diff --git a/recipe_modules/osx_sdk/api.py b/recipe_modules/osx_sdk/api.py
index 0ced868..5fff9a3 100644
--- a/recipe_modules/osx_sdk/api.py
+++ b/recipe_modules/osx_sdk/api.py
@@ -8,6 +8,7 @@
 Available only to Google-run bots."""
 
 from contextlib import contextmanager
+import re
 
 from recipe_engine import recipe_api
 from datetime import datetime, timedelta
@@ -30,6 +31,18 @@
 # runs there. See https://github.com/flutter/flutter/issues/192754.
 _INTEL_MAX_XCODE_VERSION = '17c52'
 
+# Matches simulator runtime disk image UDIDs as printed by `simctl runtime`,
+# e.g. `D: 73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2 iOS (26.2 - 23C54) (Unusable -
+# Other Failure: ... "Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916" ...)`.
+_RUNTIME_UDID_RE = re.compile(
+    r'\b[0-9A-F]{8}-[0-9A-F]{4}-[0-9A-F]{4}-[0-9A-F]{4}-[0-9A-F]{12}\b'
+)
+
+# Substring of the `simctl runtime add` output when the added image is a
+# duplicate of an already registered (possibly still deleting) image. See
+# https://github.com/flutter/flutter/issues/180141.
+_DUPLICATE_RUNTIME_ERROR = 'duplicate of'
+
 
 class OSXSDKApi(recipe_api.RecipeApi):
   """API for using OS X SDK distributed via CIPD."""
@@ -733,18 +746,14 @@
                 status=self.m.step.INFRA_FAILURE,
             )
 
-          # Skip adding the runtime if it's already mounted
-          if not self._is_runtime_mounted(runtime_version, xcode_version,
-                                          runtime_simulators):
-            self.m.step(
-                'verify and mount runtime %s' % version.lower(),
-                [
-                    'xcrun',
-                    'simctl',
-                    'runtime',
-                    'add',
-                    runtime_dmg_path,
-                ],
+          # Skip adding the runtime if it's already mounted.
+          ios_runtime_build_version = self._lookup_runtime_build_version(
+              runtime_version, xcode_version
+          )
+          if not self._is_runtime_build_listed(ios_runtime_build_version,
+                                               runtime_simulators):
+            self._mount_runtime(
+                version, runtime_dmg_path, ios_runtime_build_version
             )
 
       else:
@@ -877,7 +886,8 @@
         if parsed_xcode_version >= self.m.version.parse('15.0.0'):
           max_remaining_runtimes = 0
 
-      # Wait up to ~5 minutes until runtimes are unmounted.
+      # Wait up to ~5 minutes until runtimes are unmounted and their disk
+      # images are fully deleted.
       self.m.retry.basic_wrap(
           lambda timeout: self._is_runtimes_unmounted(
               max_remaining_runtimes,
@@ -902,32 +912,168 @@
 
   # pylint: disable=unused-argument
   def _is_runtimes_unmounted(self, max_remaining_runtimes, timeout=None):
-    '''Check if more than one runtime is currently mounted. If more than one
-    is mounted, raise a `StepFailure`.
+    '''Check if more than one runtime is currently mounted or if any runtime
+    disk image is still being deleted. If so, raise an `InfraFailure` (which
+    `retry.basic_wrap` retries; if it persists, the build is an infra failure
+    rather than a test failure).
 
     Args:
       max_remaining_runtimes: (int) How many runtimes are allowed to remain for
       it to be considered done unmounting.
     '''
-    runtime_simulators = self.m.step(
+    runtime_simulators = self._list_runtimes()
+
+    if len(runtime_simulators[1:]) > max_remaining_runtimes:
+      raise self.m.step.InfraFailure('Runtimes not unmounted yet')
+
+    # `simctl list runtimes` stops listing a runtime as soon as it is unmounted,
+    # but `simctl runtime delete` keeps the disk image registered (in the
+    # `Deleting` state) until it has been fully removed. Re-adding the same
+    # image before that finishes makes simctl register the new image as an
+    # unusable "Duplicate of" the old one, which is the root cause of
+    # https://github.com/flutter/flutter/issues/180141.
+    self._is_runtime_deletion_complete()
+
+  def _list_runtimes(self):
+    """Runs `xcrun simctl list runtimes` and returns its output lines.
+
+    Example output:
+    [
+      "== Runtimes ==",
+      "iOS 16.2 (16.2 - 20C52) - com.apple.CoreSimulator.SimRuntime.iOS-16-2",
+      "iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4"
+    ]
+    """
+    return self.m.step(
         'list runtimes', ['xcrun', 'simctl', 'list', 'runtimes'],
         stdout=self.m.raw_io.output_text(add_output_log=True)
     ).stdout.splitlines()
 
-    if len(runtime_simulators[1:]) > max_remaining_runtimes:
-      raise self.m.step.StepFailure('Runtimes not unmounted yet')
+  # pylint: disable=unused-argument
+  def _is_runtime_deletion_complete(self, timeout=None):
+    """Check if any runtime disk image is still being deleted. If so, raise an
+    `InfraFailure`.
 
-  def _is_runtime_mounted(
-      self, runtime_version, xcode_version, runtime_simulators
+    Uses `xcrun simctl runtime list` (not `simctl list runtimes`), which
+    reports the state of each runtime disk image (e.g. `Ready`, `Deleting`,
+    `Unusable`).
+    """
+    disk_images = self.m.step(
+        'list runtime disk images', ['xcrun', 'simctl', 'runtime', 'list'],
+        stdout=self.m.raw_io.output_text(add_output_log=True)
+    ).stdout
+
+    if 'Deleting' in disk_images:
+      raise self.m.step.InfraFailure('Runtime disk images not deleted yet')
+
+  def _wait_for_runtime_deletion(self):
+    """Waits up to ~5 minutes until no runtime disk image is being deleted."""
+    self.m.retry.basic_wrap(
+        lambda timeout: self._is_runtime_deletion_complete(timeout=timeout),
+        sleep=5.0,
+        backoff_factor=2,
+        max_attempts=7
+    )
+
+  def _mount_runtime(
+      self, version, runtime_dmg_path, ios_runtime_build_version
   ):
-    """Determine if iOS runtime version is already mounted.
+    """Mounts an iOS runtime dmg with `simctl runtime add`.
+
+    `simctl runtime add` fails with an `Unusable - Other Failure: ...
+    "Duplicate of <UDID>"` error when an image with the same identity is still
+    registered, typically because a previous `simctl runtime delete` of that
+    image has not finished yet (deletion is asynchronous). The runtime may
+    nevertheless be usable, so rather than failing the build outright:
+      1. wait for any pending deletions to finish,
+      2. re-check `simctl list runtimes`; if the runtime is now listed, the
+         duplicate error was benign,
+      3. otherwise delete the duplicate disk image(s) and retry the mount
+         once, failing the build if that also fails.
+    See https://github.com/flutter/flutter/issues/180141.
+
+    Args:
+      version: (string) The configured runtime version (e.g.
+        "ios-16-4_14e300c").
+      runtime_dmg_path: (string) Path to the runtime dmg to mount.
+      ios_runtime_build_version: (string) The iOS runtime build (e.g.
+        "20e247") used to verify whether the runtime is mounted.
+    """
+    step_name = 'verify and mount runtime %s' % version.lower()
+    cmd = ['xcrun', 'simctl', 'runtime', 'add', runtime_dmg_path]
+    result = self.m.step(
+        step_name,
+        cmd,
+        ok_ret='any',
+        stdout=self.m.raw_io.output_text(add_output_log=True),
+        stderr=self.m.raw_io.output_text(add_output_log=True),
+    )
+    if result.retcode == 0:
+      return
+
+    output = '%s\n%s' % (result.stdout, result.stderr)
+    if _DUPLICATE_RUNTIME_ERROR not in output.lower():
+      result.presentation.status = self.m.step.INFRA_FAILURE
+      self.m.step.empty(
+          'Failed to mount runtime %s' % version.lower(),
+          status=self.m.step.INFRA_FAILURE,
+          step_text=output.strip(),
+      )
+
+    # The presentation can only be changed until the next step starts.
+    result.presentation.step_text = (
+        'simctl reported a "Duplicate of" error (retcode %d); see the "handle '
+        'duplicate runtime %s" step.' % (result.retcode, version.lower())
+    )
+
+    with self.m.step.nest('handle duplicate runtime %s' %
+                          version.lower()) as display_step:
+      self._wait_for_runtime_deletion()
+
+      if self._is_runtime_build_listed(ios_runtime_build_version,
+                                       self._list_runtimes()):
+        display_step.step_text = (
+            'Runtime %s (%s) is already mounted; ignoring benign "Duplicate '
+            'of" error from simctl.' % (version, ios_runtime_build_version)
+        )
+        return
+
+      # The runtime is not usable, so the unusable duplicate (and the image it
+      # duplicates, which is not usable either since it is not listed) must be
+      # removed before the dmg can be added again.
+      for udid in self._parse_runtime_udids(output):
+        self.m.step(
+            'delete runtime disk image %s' % udid,
+            ['xcrun', 'simctl', 'runtime', 'delete', udid],
+            ok_ret='any',
+        )
+      self._wait_for_runtime_deletion()
+
+      self.m.step('%s (retry)' % step_name, cmd)
+
+  def _parse_runtime_udids(self, output):
+    """Returns the unique runtime disk image UDIDs found in `output`, in order.
+
+    Args:
+      output: (string) Output of a `simctl runtime` command.
+    """
+    udids = []
+    for udid in _RUNTIME_UDID_RE.findall(output.upper()):
+      if udid not in udids:
+        udids.append(udid)
+    return udids
+
+  def _lookup_runtime_build_version(self, runtime_version, xcode_version):
+    """Looks up the iOS runtime build version from CIPD.
 
     Args:
       runtime_version: (string) The iOS version (e.g. "ios-16-4").
       xcode_version: (string) The Xcode version (e.g. "14e300c").
-      runtime_simulators: (list) A list of strings of runtime versions.
     Returns:
-      A boolean for whether or not the runtime is already mounted.
+      A string of the iOS runtime build version (e.g. "20e247").
+
+    Raises:
+      InfraFailure if the build version could not be determined.
     """
 
     with self.m.step.nest('cipd describe %s_%s' %
@@ -954,10 +1100,28 @@
         )
         display_step.status = self.m.step.SUCCESS
 
-    # Check if runtime is already mounted
+    return ios_runtime_build_version
+
+  def _is_runtime_build_listed(
+      self, ios_runtime_build_version, runtime_simulators
+  ):
+    """Determine if an iOS runtime build is listed as usable by
+    `simctl list runtimes`.
+
+    Args:
+      ios_runtime_build_version: (string) The iOS runtime build (e.g. "20e247").
+      runtime_simulators: (list) Output lines of `simctl list runtimes`.
+    Returns:
+      A boolean for whether or not the runtime is mounted and usable.
+    """
     for runtime in runtime_simulators:
       # Example runtime: `iOS 14.3 (14.3 - 18C61) - com.apple.CoreSimulator.SimRuntime.iOS-14-3`
-      if ios_runtime_build_version.lower() in runtime.lower():
+      runtime = runtime.lower()
+      # A runtime reported as unavailable/unusable (e.g. an unusable duplicate
+      # disk image) does not count as mounted; it must be (re)mounted.
+      if 'unavailable' in runtime or 'unusable' in runtime:
+        continue
+      if ios_runtime_build_version.lower() in runtime:
         return True
 
     return False
diff --git a/recipe_modules/osx_sdk/examples/full.expected/explicit_package_source.json b/recipe_modules/osx_sdk/examples/full.expected/explicit_package_source.json
index 6cfcfba..71f08c2 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/explicit_package_source.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/explicit_package_source.json
@@ -240,6 +240,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -533,6 +547,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -804,6 +832,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
@@ -1063,6 +1105,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (4).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (4)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/explicit_version.json b/recipe_modules/osx_sdk/examples/full.expected/explicit_version.json
index 6a31ef1..b371253 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/explicit_version.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/explicit_version.json
@@ -240,6 +240,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -533,6 +547,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -804,6 +832,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
@@ -1063,6 +1105,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (4).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (4)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/intel_pins_xcode_to_17c52.json b/recipe_modules/osx_sdk/examples/full.expected/intel_pins_xcode_to_17c52.json
index c61abc6..70dc191 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/intel_pins_xcode_to_17c52.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/intel_pins_xcode_to_17c52.json
@@ -389,6 +389,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -660,6 +674,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -919,6 +947,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/kill_startup_assistant.json b/recipe_modules/osx_sdk/examples/full.expected/kill_startup_assistant.json
index 59d833e..067c88b 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/kill_startup_assistant.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/kill_startup_assistant.json
@@ -549,6 +549,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -877,6 +891,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1136,6 +1164,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_already_reset_invalid date.json b/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_already_reset_invalid date.json
index 6901003..8a7fcd0 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_already_reset_invalid date.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_already_reset_invalid date.json
@@ -567,6 +567,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -895,6 +909,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1154,6 +1182,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_7_days.json b/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_7_days.json
index 245cea8..f29d850 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_7_days.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_7_days.json
@@ -569,6 +569,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -897,6 +911,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1156,6 +1184,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_a_day.json b/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_a_day.json
index d5a7a19..a47166c 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_a_day.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/launch_services_unresponsive_mac_reset_within_a_day.json
@@ -569,6 +569,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -897,6 +911,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1156,6 +1184,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_arm_host.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_arm_host.json
index 1728fda..c46699d 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_13_arm_host.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_arm_host.json
@@ -382,6 +382,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -653,6 +667,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -912,6 +940,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_no_runtimes.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_no_runtimes.json
index 6a31ef1..b371253 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_no_runtimes.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_no_runtimes.json
@@ -240,6 +240,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -533,6 +547,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -804,6 +832,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
@@ -1063,6 +1105,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (4).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (4)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_runtime_deletion_never_finishes.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_runtime_deletion_never_finishes.json
new file mode 100644
index 0000000..a94924f
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_cleanup_runtime_deletion_never_finishes.json
@@ -0,0 +1,472 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "rm",
+      "-rf",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up Xcode cache"
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "Cleaning up runtimes cache",
+    "~followup_annotations": [
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "all"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up mounted simulator runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "xcodebuild",
+      "-version"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.check xcode version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@Xcode 15.0@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@Build version 15C500b@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (2)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (2)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (3)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (3)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (4)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (4)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (5)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (5)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "Cleaning up runtimes cache.sleep 80",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (6)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (6)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "Cleaning up runtimes cache.sleep 160",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (7)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (7)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "failure": {
+      "humanReason": "Runtime disk images not deleted yet"
+    },
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_already_mounted.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_already_mounted.json
index ae66416..05a4d70 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_already_mounted.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_already_mounted.json
@@ -672,6 +672,20 @@
   },
   {
     "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
       "vpython3",
       "-u",
       "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_clean.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_clean.json
index 1808374..751653c 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_clean.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_clean.json
@@ -277,6 +277,51 @@
   },
   {
     "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes (4)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images (2)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
       "vpython3",
       "-u",
       "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
@@ -425,7 +470,8 @@
     "infra_step": true,
     "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
     "~followup_annotations": [
-      "@@@STEP_NEST_LEVEL@1@@@"
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
     ]
   },
   {
@@ -640,6 +686,20 @@
   },
   {
     "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
       "vpython3",
       "-u",
       "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
@@ -839,6 +899,20 @@
   },
   {
     "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
       "vpython3",
       "-u",
       "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_not_mounted.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_not_mounted.json
index 61cfb00..b5e0295 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_not_mounted.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_explicit_runtime_version_not_mounted.json
@@ -359,7 +359,8 @@
     "infra_step": true,
     "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
     "~followup_annotations": [
-      "@@@STEP_NEST_LEVEL@1@@@"
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
     ]
   },
   {
@@ -685,6 +686,20 @@
   },
   {
     "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
       "vpython3",
       "-u",
       "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_already_mounted.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_already_mounted.json
new file mode 100644
index 0000000..e47cb49
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_already_mounted.json
@@ -0,0 +1,771 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install-runtime-dmg",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-runtime-version",
+      "ios-16-4",
+      "-xcode-version",
+      "14e300c",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.install xcode runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "listdir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list xcode runtime dmg ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg@@@",
+      "@@@STEP_LOG_END@listdir@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "cipd",
+      "describe",
+      "infra_internal/ios/xcode/ios_runtime_dmg",
+      "-version",
+      "14e300c",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"pin\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"instance_id\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"package\": \"xxx\"@@@",
+      "@@@STEP_LOG_LINE@json.output@    },@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"tags\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_build:20e247\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      },@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_version:ios-16-4\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.runtime build version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_TEXT@20e247@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@simctl reported a \"Duplicate of\" error (retcode 5); see the \"handle duplicate runtime ios-16-4_14e300c\" step.@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Runtime ios-16-4_14e300c (20e247) is already mounted; ignoring benign \"Duplicate of\" error from simctl.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Ready@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "gn",
+      "gen",
+      "out/Release"
+    ],
+    "name": "gn"
+  },
+  {
+    "cmd": [
+      "ninja",
+      "-C",
+      "out/Release"
+    ],
+    "name": "ninja"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode (2)"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CLEANUP]/tmp_tmp_1/osx_sdk",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CLEANUP]/tmp_tmp_1/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CLEANUP]/tmp_tmp_1/osx_sdk/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "/opt/flutter/xcode/17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode (2)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators (2)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "list runtimes (2)",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "rmtree",
+      "/opt/flutter/xcode/17c52"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up Xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode (3)"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CLEANUP]/tmp_tmp_2/osx_sdk",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CLEANUP]/tmp_tmp_2/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CLEANUP]/tmp_tmp_2/osx_sdk/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "/opt/flutter/xcode/17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "Cleaning up runtimes cache"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "all"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up mounted simulator runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "xcodebuild",
+      "-version"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.check xcode version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "rmtree",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up runtime cache ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart (3)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode (3)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators (3)"
+  },
+  {
+    "cmd": [
+      "gn",
+      "gen",
+      "out/Release"
+    ],
+    "name": "gn (2)"
+  },
+  {
+    "cmd": [
+      "ninja",
+      "-C",
+      "out/Release"
+    ],
+    "name": "ninja (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode (3)"
+  },
+  {
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_deletion_never_finishes.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_deletion_never_finishes.json
new file mode 100644
index 0000000..d8ac4f2
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_deletion_never_finishes.json
@@ -0,0 +1,466 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes",
+    "~followup_annotations": [
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install-runtime-dmg",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-runtime-version",
+      "ios-16-4",
+      "-xcode-version",
+      "14e300c",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.install xcode runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "listdir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list xcode runtime dmg ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg@@@",
+      "@@@STEP_LOG_END@listdir@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "cipd",
+      "describe",
+      "infra_internal/ios/xcode/ios_runtime_dmg",
+      "-version",
+      "14e300c",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"pin\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"instance_id\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"package\": \"xxx\"@@@",
+      "@@@STEP_LOG_LINE@json.output@    },@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"tags\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_build:20e247\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      },@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_version:ios-16-4\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.runtime build version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_TEXT@20e247@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@simctl reported a \"Duplicate of\" error (retcode 5); see the \"handle duplicate runtime ios-16-4_14e300c\" step.@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (2)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (3)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (4)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (5)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.sleep 80",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (6)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.sleep 160",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (7)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "failure": {
+      "humanReason": "Runtime disk images not deleted yet"
+    },
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_retry_fails.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_retry_fails.json
new file mode 100644
index 0000000..a86df21
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_retry_fails.json
@@ -0,0 +1,425 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes",
+    "~followup_annotations": [
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install-runtime-dmg",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-runtime-version",
+      "ios-16-4",
+      "-xcode-version",
+      "14e300c",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.install xcode runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "listdir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list xcode runtime dmg ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg@@@",
+      "@@@STEP_LOG_END@listdir@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "cipd",
+      "describe",
+      "infra_internal/ios/xcode/ios_runtime_dmg",
+      "-version",
+      "14e300c",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"pin\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"instance_id\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"package\": \"xxx\"@@@",
+      "@@@STEP_LOG_LINE@json.output@    },@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"tags\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_build:20e247\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      },@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_version:ios-16-4\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.runtime build version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_TEXT@20e247@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@simctl reported a \"Duplicate of\" error (retcode 5); see the \"handle duplicate runtime ios-16-4_14e300c\" step.@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.delete runtime disk image 73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "30BC4E5F-DE5F-499A-93AF-22FEF83EF916"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.delete runtime disk image 30BC4E5F-DE5F-499A-93AF-22FEF83EF916",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (2)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.verify and mount runtime ios-16-4_14e300c (retry)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "failure": {
+      "humanReason": "Infra Failure: Step('install runtimes.handle duplicate runtime ios-16-4_14e300c.verify and mount runtime ios-16-4_14e300c (retry)') (retcode: 5)"
+    },
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_retry_succeeds.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_retry_succeeds.json
new file mode 100644
index 0000000..ae3a6f9
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_duplicate_retry_succeeds.json
@@ -0,0 +1,844 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install-runtime-dmg",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-runtime-version",
+      "ios-16-4",
+      "-xcode-version",
+      "14e300c",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.install xcode runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "listdir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list xcode runtime dmg ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg@@@",
+      "@@@STEP_LOG_END@listdir@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "cipd",
+      "describe",
+      "infra_internal/ios/xcode/ios_runtime_dmg",
+      "-version",
+      "14e300c",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"pin\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"instance_id\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"package\": \"xxx\"@@@",
+      "@@@STEP_LOG_LINE@json.output@    },@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"tags\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_build:20e247\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      },@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_version:ios-16-4\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.runtime build version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_TEXT@20e247@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@simctl reported a \"Duplicate of\" error (retcode 5); see the \"handle duplicate runtime ios-16-4_14e300c\" step.@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@D: 73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2 iOS (16.4 - 20E247) (Unusable - Other Failure: Error Domain=SimDiskImageErrorDomain Code=5 \"Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916\" UserInfo={NSLocalizedDescription=Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916, unusableErrorDetail=})@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 6.6GB - Deleting@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 0 bytes - Unusable - Other Failure: Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (2)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Disk Images ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (20E247) - 0 bytes - Unusable - Other Failure: Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4 (unavailable, runtime is unusable)@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.delete runtime disk image 73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "30BC4E5F-DE5F-499A-93AF-22FEF83EF916"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.delete runtime disk image 30BC4E5F-DE5F-499A-93AF-22FEF83EF916",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (3)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.handle duplicate runtime ios-16-4_14e300c.verify and mount runtime ios-16-4_14e300c (retry)",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "gn",
+      "gen",
+      "out/Release"
+    ],
+    "name": "gn"
+  },
+  {
+    "cmd": [
+      "ninja",
+      "-C",
+      "out/Release"
+    ],
+    "name": "ninja"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode (2)"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CLEANUP]/tmp_tmp_1/osx_sdk",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CLEANUP]/tmp_tmp_1/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CLEANUP]/tmp_tmp_1/osx_sdk/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "/opt/flutter/xcode/17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode (2)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators (2)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "list runtimes (2)",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "rmtree",
+      "/opt/flutter/xcode/17c52"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up Xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode (3)"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CLEANUP]/tmp_tmp_2/osx_sdk",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CLEANUP]/tmp_tmp_2/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CLEANUP]/tmp_tmp_2/osx_sdk/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "/opt/flutter/xcode/17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "Cleaning up runtimes cache"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "all"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up mounted simulator runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "xcodebuild",
+      "-version"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.check xcode version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "rmtree",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up runtime cache ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart (3)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode (3)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators (3)"
+  },
+  {
+    "cmd": [
+      "gn",
+      "gen",
+      "out/Release"
+    ],
+    "name": "gn (2)"
+  },
+  {
+    "cmd": [
+      "ninja",
+      "-C",
+      "out/Release"
+    ],
+    "name": "ninja (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode (3)"
+  },
+  {
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_listed_unavailable_is_mounted.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_listed_unavailable_is_mounted.json
new file mode 100644
index 0000000..9f51f23
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_listed_unavailable_is_mounted.json
@@ -0,0 +1,731 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4 (unavailable, runtime profile not found)@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install-runtime-dmg",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-runtime-version",
+      "ios-16-4",
+      "-xcode-version",
+      "14e300c",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.install xcode runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "listdir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list xcode runtime dmg ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg@@@",
+      "@@@STEP_LOG_END@listdir@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "cipd",
+      "describe",
+      "infra_internal/ios/xcode/ios_runtime_dmg",
+      "-version",
+      "14e300c",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"pin\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"instance_id\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"package\": \"xxx\"@@@",
+      "@@@STEP_LOG_LINE@json.output@    },@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"tags\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_build:20e247\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      },@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_version:ios-16-4\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.runtime build version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_TEXT@20e247@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "gn",
+      "gen",
+      "out/Release"
+    ],
+    "name": "gn"
+  },
+  {
+    "cmd": [
+      "ninja",
+      "-C",
+      "out/Release"
+    ],
+    "name": "ninja"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode (2)"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CLEANUP]/tmp_tmp_1/osx_sdk",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CLEANUP]/tmp_tmp_1/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CLEANUP]/tmp_tmp_1/osx_sdk/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "/opt/flutter/xcode/17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode (2).install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode (2)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators (2)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "list runtimes (2)",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "rmtree",
+      "/opt/flutter/xcode/17c52"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up Xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode (3)"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CLEANUP]/tmp_tmp_2/osx_sdk",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CLEANUP]/tmp_tmp_2/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CLEANUP]/tmp_tmp_2/osx_sdk/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "/opt/flutter/xcode/17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode (3).install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "Cleaning up runtimes cache"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "delete",
+      "all"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up mounted simulator runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "xcodebuild",
+      "-version"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.check xcode version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "rmtree",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.Cleaning up runtime cache ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "killall",
+      "-9",
+      "-v",
+      "com.apple.CoreSimulator.CoreSimulatorDevice"
+    ],
+    "infra_step": true,
+    "name": "kill dart (3)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "/opt/flutter/xcode/17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "select xcode (3)"
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "list simulators (3)"
+  },
+  {
+    "cmd": [
+      "gn",
+      "gen",
+      "out/Release"
+    ],
+    "name": "gn (2)"
+  },
+  {
+    "cmd": [
+      "ninja",
+      "-C",
+      "out/Release"
+    ],
+    "name": "ninja (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode (2)"
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode (3)"
+  },
+  {
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_mount_fails.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_mount_fails.json
new file mode 100644
index 0000000..e708e0f
--- /dev/null
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_runtime_mount_fails.json
@@ -0,0 +1,342 @@
+[
+  {
+    "cmd": [
+      "sw_vers",
+      "-productVersion"
+    ],
+    "name": "find macOS version"
+  },
+  {
+    "cmd": [],
+    "name": "Pinning Xcode to 17c52 on Intel",
+    "~followup_annotations": [
+      "@@@STEP_TEXT@Requested Xcode deadbeef, but Intel bots cannot run macOS 26. See https://github.com/flutter/flutter/issues/192754.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "pgrep",
+      "Setup Assistant"
+    ],
+    "infra_step": true,
+    "name": "check for Setup Assistant",
+    "~followup_annotations": [
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "verify launch services"
+  },
+  {
+    "cmd": [
+      "/System/Library/Frameworks/CoreServices.framework/Frameworks/LaunchServices.framework/Support/lsregister",
+      "-kill",
+      "-r",
+      "-domain",
+      "local",
+      "-domain",
+      "system",
+      "-domain",
+      "user"
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Reset and rescan Launch Services db",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "log",
+      "show",
+      "--last",
+      "24h",
+      "--style",
+      "compact",
+      "--predicate",
+      "logType == \"error\" AND process == \"xcodebuild\" AND subsystem == \"com.apple.launchservices\" AND composedMessage CONTAINS \"disconnect event interruption received for service\""
+    ],
+    "infra_step": true,
+    "name": "verify launch services.Check if xcodebuild impacted by Launch Services",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "echo",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "show app_dir"
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache"
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk."
+  },
+  {
+    "cmd": [],
+    "name": "Running Cache Micro Manager on [CACHE]/osx_sdk..Cache Micro Manager, cache directory exists check",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Cache dir does not exist, skipping.@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk"
+    ],
+    "infra_step": true,
+    "name": "Show xcode cache (2)"
+  },
+  {
+    "cmd": [],
+    "name": "install xcode"
+  },
+  {
+    "cmd": [
+      "cipd",
+      "ensure",
+      "-root",
+      "[CACHE]/osx_sdk/xcode_17c52",
+      "-ensure-file",
+      "infra/tools/mac_toolchain/${platform} 123abc",
+      "-max-threads",
+      "0",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install xcode.ensure_installed",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"instance_id\": \"resolved-instance_id-of-123abc----------\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"package\": \"infra/tools/mac_toolchain/resolved-platform\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "ls",
+      "-al",
+      "[CACHE]/osx_sdk/xcode_17c52"
+    ],
+    "infra_step": true,
+    "name": "install xcode.Show tool_dir cache",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install",
+      "-kind",
+      "mac",
+      "-xcode-version",
+      "17c52",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-with-runtime=False",
+      "-with-metal-toolchain=True",
+      "-verbose"
+    ],
+    "infra_step": true,
+    "name": "install xcode.install xcode from cipd",
+    "timeout": 1800,
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes",
+    "~followup_annotations": [
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--switch",
+      "[CACHE]/osx_sdk/xcode_17c52/XCode.app"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.select xcode",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "list",
+      "runtimes"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list runtimes",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@== Runtimes ==@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "[CACHE]/osx_sdk/xcode_17c52/mac_toolchain",
+      "install-runtime-dmg",
+      "-cipd-package-prefix",
+      "infra_internal/ios/xcode",
+      "-runtime-version",
+      "ios-16-4",
+      "-xcode-version",
+      "14e300c",
+      "-output-dir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.install xcode runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "vpython3",
+      "-u",
+      "RECIPE_MODULE[recipe_engine::file]/resources/fileutil.py",
+      "--json-output",
+      "/path/to/tmp/json",
+      "listdir",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.list xcode runtime dmg ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd@@@",
+      "@@@STEP_LOG_LINE@listdir@[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg@@@",
+      "@@@STEP_LOG_END@listdir@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "cipd",
+      "describe",
+      "infra_internal/ios/xcode/ios_runtime_dmg",
+      "-version",
+      "14e300c",
+      "-json-output",
+      "/path/to/tmp/json"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_LOG_LINE@json.output@{@@@",
+      "@@@STEP_LOG_LINE@json.output@  \"result\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"pin\": {@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"instance_id\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@      \"package\": \"xxx\"@@@",
+      "@@@STEP_LOG_LINE@json.output@    },@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@    \"tags\": [@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_build:20e247\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      },@@@",
+      "@@@STEP_LOG_LINE@json.output@      {@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_by\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"registered_ts\": \"xxx\",@@@",
+      "@@@STEP_LOG_LINE@json.output@        \"tag\": \"ios_runtime_version:ios-16-4\"@@@",
+      "@@@STEP_LOG_LINE@json.output@      }@@@",
+      "@@@STEP_LOG_LINE@json.output@    ]@@@",
+      "@@@STEP_LOG_LINE@json.output@  }@@@",
+      "@@@STEP_LOG_LINE@json.output@}@@@",
+      "@@@STEP_LOG_END@json.output@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.cipd describe ios-16-4_14e300c.runtime build version",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@2@@@",
+      "@@@STEP_TEXT@20e247@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "add",
+      "[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg"
+    ],
+    "infra_step": true,
+    "name": "install runtimes.verify and mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_LINE@raw_io.output_text@Error Domain=SimDiskImageErrorDomain Code=1 \"Unable to verify image\"@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@",
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [],
+    "name": "install runtimes.Failed to mount runtime ios-16-4_14e300c",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_TEXT@Error Domain=SimDiskImageErrorDomain Code=1 \"Unable to verify image\"@@@",
+      "@@@STEP_EXCEPTION@@@"
+    ]
+  },
+  {
+    "cmd": [
+      "sudo",
+      "xcode-select",
+      "--reset"
+    ],
+    "infra_step": true,
+    "name": "reset XCode"
+  },
+  {
+    "failure": {
+      "humanReason": "Infra Failure: Step('install runtimes.Failed to mount runtime ios-16-4_14e300c') (retcode: 0)"
+    },
+    "name": "$result"
+  }
+]
\ No newline at end of file
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_13_x86_host.json b/recipe_modules/osx_sdk/examples/full.expected/mac_13_x86_host.json
index 34698a1..b7f4468 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_13_x86_host.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_13_x86_host.json
@@ -389,6 +389,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -660,6 +674,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -919,6 +947,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_26_launch_services_errors_without_reset.json b/recipe_modules/osx_sdk/examples/full.expected/mac_26_launch_services_errors_without_reset.json
index ad8aad1..9da9ffa 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_26_launch_services_errors_without_reset.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_26_launch_services_errors_without_reset.json
@@ -537,6 +537,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -865,6 +879,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1124,6 +1152,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/mac_26_skips_launch_services_reset.json b/recipe_modules/osx_sdk/examples/full.expected/mac_26_skips_launch_services_reset.json
index f5e78ff..7db5245 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/mac_26_skips_launch_services_reset.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/mac_26_skips_launch_services_reset.json
@@ -530,6 +530,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -858,6 +872,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1117,6 +1145,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/no_runtime_version.json b/recipe_modules/osx_sdk/examples/full.expected/no_runtime_version.json
index f47ce92..6aa5143 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/no_runtime_version.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/no_runtime_version.json
@@ -521,6 +521,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -849,6 +863,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1108,6 +1136,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/unavailable_runtime_arm_on_intel.json b/recipe_modules/osx_sdk/examples/full.expected/unavailable_runtime_arm_on_intel.json
index 5306ea6..d339f80 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/unavailable_runtime_arm_on_intel.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/unavailable_runtime_arm_on_intel.json
@@ -391,6 +391,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -662,6 +676,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.expected/xcode_install_fails_passes_on_retry.json b/recipe_modules/osx_sdk/examples/full.expected/xcode_install_fails_passes_on_retry.json
index 61f314b..15b1c07 100644
--- a/recipe_modules/osx_sdk/examples/full.expected/xcode_install_fails_passes_on_retry.json
+++ b/recipe_modules/osx_sdk/examples/full.expected/xcode_install_fails_passes_on_retry.json
@@ -484,6 +484,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
@@ -900,6 +914,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (2).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (2)"
   },
@@ -1228,6 +1256,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (3).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (3)"
   },
@@ -1487,6 +1529,20 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "infra_step": true,
+    "name": "Cleaning up runtimes cache (4).list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes (4)"
   },
diff --git a/recipe_modules/osx_sdk/examples/full.py b/recipe_modules/osx_sdk/examples/full.py
index fca51d6..81aa286 100644
--- a/recipe_modules/osx_sdk/examples/full.py
+++ b/recipe_modules/osx_sdk/examples/full.py
@@ -24,6 +24,120 @@
     return_value=datetime(2023, 12, 15, 13, 43, 21, 621929)
 )  # 2023-12-15 13:43:21
 
+# Output of `xcrun simctl runtime add` when the image is a duplicate of one
+# that is still registered (e.g. still being deleted). Copied from the failing
+# build in https://github.com/flutter/flutter/issues/180141.
+_DUPLICATE_RUNTIME_OUTPUT = (
+    'D: 73EA5108-FE5E-4ADC-B6A6-D2FBE4448EA2 iOS (16.4 - 20E247) (Unusable - '
+    'Other Failure: Error Domain=SimDiskImageErrorDomain Code=5 "Duplicate of '
+    '30BC4E5F-DE5F-499A-93AF-22FEF83EF916" UserInfo={NSLocalizedDescription='
+    'Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916, unusableErrorDetail=})'
+)
+
+_RUNTIME_16_4_LISTED = (
+    '== Runtimes ==\n' +
+    'iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4'
+)
+
+_RUNTIME_DMG_CIPD_DESCRIPTION = {
+    'result': {
+        'pin': {
+            'package': 'xxx',
+            'instance_id': 'xxx'
+        },
+        'registered_by':
+            'xxx',
+        'registered_ts':
+            'xxx',
+        'tags': [
+            {
+                'tag': 'ios_runtime_build:20e247',
+                'registered_by': 'xxx',
+                'registered_ts': 'xxx'
+            },
+            {
+                'tag': 'ios_runtime_version:ios-16-4',
+                'registered_by': 'xxx',
+                'registered_ts': 'xxx'
+            },
+        ],
+    }
+}
+
+# Number of `list runtime disk images` attempts made while waiting for runtime
+# deletions to finish (`max_attempts` of the `retry.basic_wrap` in
+# `_wait_for_runtime_deletion` / the runtimes cache cleanup).
+_DELETION_WAIT_ATTEMPTS = 7
+
+_RUNTIME_DISK_IMAGE_DELETING = (
+    '== Disk Images ==\n' + 'iOS 16.4 (20E247) - 6.6GB - Deleting'
+)
+
+
+def _runtime_disk_images_deleting(api, step_name, attempts):
+  """Test data making `attempts` consecutive `list runtime disk images` steps
+  (named `step_name`, `step_name (2)`, ...) report an image being deleted.
+  """
+  test_data = api.empty_test_data()
+  for attempt in range(attempts):
+    name = step_name if attempt == 0 else '%s (%d)' % (step_name, attempt + 1)
+    test_data += api.step_data(
+        name, stdout=api.raw_io.output_text(_RUNTIME_DISK_IMAGE_DELETING)
+    )
+  return test_data
+
+
+def _mac_13_runtime_not_mounted(
+    api, install_list_runtimes='== Runtimes ==\n', fails=False
+):
+  """Test data for a macOS 13 host with one explicit runtime that is not
+  mounted yet, so that `install runtimes` has to mount the dmg.
+
+  Args:
+    install_list_runtimes: (string) Output of `install runtimes.list runtimes`.
+    fails: (bool) Whether the test is expected to fail before the runtimes
+      are listed again after the Xcode setup.
+  """
+  test_data = [
+      api.platform.name('mac'),
+      api.step_data(
+          "find macOS version",
+          stdout=api.raw_io.output_text("13.5.1"),
+      ),
+      api.properties(
+          **{
+              '$flutter/osx_sdk': {
+                  'sdk_version': 'deadbeef',
+                  'toolchain_ver_intel': '123abc',
+                  'runtime_versions': ['ios-16-4_14e300c']
+              }
+          }
+      ),
+      api.step_data(
+          'install runtimes.list runtimes',
+          stdout=api.raw_io.output_text(install_list_runtimes)
+      ),
+      api.step_data(
+          'install runtimes.list xcode runtime dmg ios-16-4_14e300c',
+          stdout=api.raw_io.output_text(
+              '[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/.cipd\n' +
+              '[CACHE]/osx_sdk/xcode_runtime_dmg_ios-16-4_14e300c/iOS_16-4.dmg'
+          )
+      ),
+      api.step_data(
+          'install runtimes.cipd describe ios-16-4_14e300c.cipd describe infra_internal/ios/xcode/ios_runtime_dmg',
+          api.json.output(_RUNTIME_DMG_CIPD_DESCRIPTION),
+      ),
+  ]
+  if not fails:
+    test_data.append(
+        api.step_data(
+            'list runtimes',
+            stdout=api.raw_io.output_text(_RUNTIME_16_4_LISTED)
+        )
+    )
+  return sum(test_data, api.empty_test_data())
+
 
 def RunSteps(api):
   api.osx_sdk.now = _MOCK_TIME_NOW
@@ -294,6 +408,175 @@
       ),
   )
 
+  # Tests for https://github.com/flutter/flutter/issues/180141: `simctl runtime
+  # add` fails with a "Duplicate of <UDID>" error.
+
+  # (a) The duplicate error is benign: the runtime is listed after re-checking.
+  yield api.test(
+      'mac_13_runtime_duplicate_already_mounted',
+      _mac_13_runtime_not_mounted(api),
+      api.step_data(
+          'install runtimes.verify and mount runtime ios-16-4_14e300c',
+          retcode=5,
+          stdout=api.raw_io.output_text(_DUPLICATE_RUNTIME_OUTPUT),
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images',
+          stdout=api.raw_io.output_text(
+              '== Disk Images ==\n' +
+              'iOS 16.4 (20E247) - 6.6GB - Ready'
+          )
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtimes',
+          stdout=api.raw_io.output_text(_RUNTIME_16_4_LISTED)
+      ),
+  )
+
+  # (b) The runtime is not listed after the duplicate error (the duplicated
+  # image was still being deleted): the duplicate images are deleted and the
+  # mount is retried successfully.
+  yield api.test(
+      'mac_13_runtime_duplicate_retry_succeeds',
+      _mac_13_runtime_not_mounted(api),
+      api.step_data(
+          'install runtimes.verify and mount runtime ios-16-4_14e300c',
+          retcode=5,
+          stderr=api.raw_io.output_text(_DUPLICATE_RUNTIME_OUTPUT),
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images',
+          stdout=api.raw_io.output_text(
+              '== Disk Images ==\n' +
+              'iOS 16.4 (20E247) - 6.6GB - Deleting\n' +
+              'iOS 16.4 (20E247) - 0 bytes - Unusable - Other Failure: Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916'
+          )
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images (2)',
+          stdout=api.raw_io.output_text(
+              '== Disk Images ==\n' +
+              'iOS 16.4 (20E247) - 0 bytes - Unusable - Other Failure: Duplicate of 30BC4E5F-DE5F-499A-93AF-22FEF83EF916'
+          )
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtimes',
+          stdout=api.raw_io.output_text(
+              '== Runtimes ==\n' +
+              'iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4 (unavailable, runtime is unusable)'
+          )
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.delete runtime disk image 30BC4E5F-DE5F-499A-93AF-22FEF83EF916',
+          retcode=2,
+          stdout=api.raw_io.output_text('No matching images found to delete'),
+      ),
+  )
+
+  # (c) The duplicate error persists after deleting the duplicate images and
+  # retrying: the build fails with an infra failure.
+  yield api.test(
+      'mac_13_runtime_duplicate_retry_fails',
+      _mac_13_runtime_not_mounted(api, fails=True),
+      api.step_data(
+          'install runtimes.verify and mount runtime ios-16-4_14e300c',
+          retcode=5,
+          stdout=api.raw_io.output_text(_DUPLICATE_RUNTIME_OUTPUT),
+      ),
+      api.step_data(
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.verify and mount runtime ios-16-4_14e300c (retry)',
+          retcode=5,
+          stdout=api.raw_io.output_text(_DUPLICATE_RUNTIME_OUTPUT),
+      ),
+      status='INFRA_FAILURE',
+  )
+
+  # (d) A mount failure that is not a duplicate error still fails the build.
+  yield api.test(
+      'mac_13_runtime_mount_fails',
+      _mac_13_runtime_not_mounted(api, fails=True),
+      api.step_data(
+          'install runtimes.verify and mount runtime ios-16-4_14e300c',
+          retcode=1,
+          stderr=api.raw_io.output_text(
+              'Error Domain=SimDiskImageErrorDomain Code=1 "Unable to verify image"'
+          ),
+      ),
+      status='INFRA_FAILURE',
+  )
+
+  # (e) A runtime that is listed but unavailable does not count as mounted and
+  # is mounted again.
+  yield api.test(
+      'mac_13_runtime_listed_unavailable_is_mounted',
+      _mac_13_runtime_not_mounted(
+          api,
+          install_list_runtimes=(
+              '== Runtimes ==\n' +
+              'iOS 16.4 (16.4 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4 (unavailable, runtime profile not found)'
+          )
+      ),
+      api.post_process(
+          post_process.MustRun,
+          'install runtimes.verify and mount runtime ios-16-4_14e300c'
+      ),
+  )
+
+  # (f) The duplicated image never leaves the `Deleting` state within the
+  # wait: the build fails with an infra failure (not a test failure).
+  yield api.test(
+      'mac_13_runtime_duplicate_deletion_never_finishes',
+      _mac_13_runtime_not_mounted(api, fails=True),
+      api.step_data(
+          'install runtimes.verify and mount runtime ios-16-4_14e300c',
+          retcode=5,
+          stdout=api.raw_io.output_text(_DUPLICATE_RUNTIME_OUTPUT),
+      ),
+      _runtime_disk_images_deleting(
+          api,
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtime disk images',
+          _DELETION_WAIT_ATTEMPTS,
+      ),
+      api.post_process(
+          post_process.DoesNotRun,
+          'install runtimes.handle duplicate runtime ios-16-4_14e300c.list runtimes'
+      ),
+      status='INFRA_FAILURE',
+  )
+
+  # (g) After `simctl runtime delete all`, a disk image never leaves the
+  # `Deleting` state within the wait: the build fails with an infra failure.
+  yield api.test(
+      'mac_13_cleanup_runtime_deletion_never_finishes',
+      api.platform.name('mac'),
+      api.step_data(
+          "find macOS version",
+          stdout=api.raw_io.output_text("13.5.1"),
+      ),
+      api.properties(
+          **{
+              '$flutter/osx_sdk': {
+                  'sdk_version': 'deadbeef',
+                  'toolchain_ver_intel': '123abc',
+                  'runtime_versions': ['ios-16-4_14e300c'],
+                  'cleanup_cache': True,
+              }
+          }
+      ),
+      api.step_data(
+          'Cleaning up runtimes cache.check xcode version',
+          stdout=api.raw_io
+          .output_text('Xcode 15.0\n' + 'Build version 15C500b')
+      ),
+      _runtime_disk_images_deleting(
+          api,
+          'Cleaning up runtimes cache.list runtime disk images',
+          _DELETION_WAIT_ATTEMPTS,
+      ),
+      api.post_process(post_process.DoesNotRun, 'install runtimes'),
+      status='INFRA_FAILURE',
+  )
+
   yield api.test(
       'mac_13_explicit_runtime_version_build_verion_failure',
       api.platform.name('mac'),
@@ -420,6 +703,20 @@
               'iOS 16.4 (16.2 - 20E247) - com.apple.CoreSimulator.SimRuntime.iOS-16-4'
           )
       ),
+      # The runtime is no longer listed but its disk image is still being
+      # deleted; the cleanup must wait for the deletion to finish to avoid
+      # a "Duplicate of" error when the dmg is added again.
+      api.step_data(
+          'Cleaning up runtimes cache.list runtime disk images',
+          stdout=api.raw_io.output_text(
+              '== Disk Images ==\n' +
+              'iOS 16.4 (20E247) - 6.6GB - Deleting'
+          )
+      ),
+      api.step_data(
+          'Cleaning up runtimes cache.list runtime disk images (2)',
+          stdout=api.raw_io.output_text('== Disk Images ==\n')
+      ),
       api.step_data(
           'install runtimes.list xcode runtime dmg ios-16-4_14e300c',
           stdout=api.raw_io.output_text(
diff --git a/recipes/devicelab/devicelab_drone_build_test.expected/xcode-mac.json b/recipes/devicelab/devicelab_drone_build_test.expected/xcode-mac.json
index 57f7324..3c04aa9 100644
--- a/recipes/devicelab/devicelab_drone_build_test.expected/xcode-mac.json
+++ b/recipes/devicelab/devicelab_drone_build_test.expected/xcode-mac.json
@@ -1710,6 +1710,53 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "cwd": "[CLEANUP]/tmp_tmp_1/flutter sdk/dev/devicelab",
+    "env": {
+      "ARTIFACT_HUB_REPOSITORY": "artifactregistry://us-maven.pkg.dev/artifact-foundry-prod/maven-3p",
+      "DEPOT_TOOLS": "RECIPE_REPO[depot_tools]",
+      "GIT_BRANCH": "master",
+      "LUCI_BRANCH": "",
+      "LUCI_CI": "True",
+      "LUCI_PR": "",
+      "OS": "darwin",
+      "PUB_CACHE": "[START_DIR]/.pub-cache",
+      "REVISION": "12345abcde12345abcde12345abcde12345abcde",
+      "SDK_CHECKOUT_PATH": "[CLEANUP]/tmp_tmp_1/flutter sdk"
+    },
+    "env_prefixes": {
+      "PATH": [
+        "[CLEANUP]/tmp_tmp_1/flutter sdk/bin",
+        "[CLEANUP]/tmp_tmp_1/flutter sdk/bin/cache/dart-sdk/bin",
+        "[CLEANUP]/tmp_tmp_1/flutter sdk/bin",
+        "[CLEANUP]/tmp_tmp_1/flutter sdk/bin/cache/dart-sdk/bin"
+      ]
+    },
+    "infra_step": true,
+    "luci_context": {
+      "realm": {
+        "name": "project:ci"
+      },
+      "resultdb": {
+        "current_invocation": {
+          "name": "invocations/build:8945511751514863184",
+          "update_token": "token"
+        },
+        "hostname": "rdbhost"
+      }
+    },
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },
diff --git a/recipes/devicelab/devicelab_test_drone.expected/mac.json b/recipes/devicelab/devicelab_test_drone.expected/mac.json
index 01263ef..771fdc5 100644
--- a/recipes/devicelab/devicelab_test_drone.expected/mac.json
+++ b/recipes/devicelab/devicelab_test_drone.expected/mac.json
@@ -1409,6 +1409,53 @@
     ]
   },
   {
+    "cmd": [
+      "xcrun",
+      "simctl",
+      "runtime",
+      "list"
+    ],
+    "cwd": "[CLEANUP]/tmp_tmp_1/flutter sdk/dev/devicelab",
+    "env": {
+      "ARTIFACT_HUB_REPOSITORY": "artifactregistry://us-maven.pkg.dev/artifact-foundry-prod/maven-3p",
+      "DEPOT_TOOLS": "RECIPE_REPO[depot_tools]",
+      "FLUTTER_LOGS_DIR": "[CLEANUP]/flutter_logs_dir",
+      "FLUTTER_TEST_OUTPUTS_DIR": "[CLEANUP]/flutter_logs_dir",
+      "GIT_BRANCH": "master",
+      "LUCI_BRANCH": "",
+      "LUCI_CI": "True",
+      "LUCI_PR": "",
+      "OS": "darwin",
+      "PUB_CACHE": "[START_DIR]/.pub-cache",
+      "REVISION": "12345abcde12345abcde12345abcde12345abcde",
+      "SDK_CHECKOUT_PATH": "[CLEANUP]/tmp_tmp_1/flutter sdk"
+    },
+    "env_prefixes": {
+      "PATH": [
+        "[CLEANUP]/tmp_tmp_1/flutter sdk/bin",
+        "[CLEANUP]/tmp_tmp_1/flutter sdk/bin/cache/dart-sdk/bin"
+      ]
+    },
+    "infra_step": true,
+    "luci_context": {
+      "realm": {
+        "name": "project:ci"
+      },
+      "resultdb": {
+        "current_invocation": {
+          "name": "invocations/build:8945511751514863184",
+          "update_token": "token"
+        },
+        "hostname": "rdbhost"
+      }
+    },
+    "name": "Cleaning up runtimes cache.list runtime disk images",
+    "~followup_annotations": [
+      "@@@STEP_NEST_LEVEL@1@@@",
+      "@@@STEP_LOG_END@raw_io.output_text@@@"
+    ]
+  },
+  {
     "cmd": [],
     "name": "install runtimes"
   },