diff --git a/packages/flutter_tools/lib/src/devfs.dart b/packages/flutter_tools/lib/src/devfs.dart
index c4ba45c..8795c4d 100644
--- a/packages/flutter_tools/lib/src/devfs.dart
+++ b/packages/flutter_tools/lib/src/devfs.dart
@@ -289,7 +289,7 @@
     while ((_inFlight < kMaxInFlight) && (!_completer.isCompleted) && _outstanding.isNotEmpty) {
       final Uri deviceUri = _outstanding.keys.first;
       final DevFSContent content = _outstanding.remove(deviceUri);
-      _startWrite(deviceUri, content);
+      _startWrite(deviceUri, content, retry: 10);
       _inFlight += 1;
     }
     if ((_inFlight == 0) && (!_completer.isCompleted) && _outstanding.isEmpty) {
@@ -299,22 +299,33 @@
 
   Future<void> _startWrite(
     Uri deviceUri,
-    DevFSContent content, [
+    DevFSContent content, {
     int retry = 0,
-  ]) async {
-    try {
-      final HttpClientRequest request = await _client.putUrl(httpAddress);
-      request.headers.removeAll(HttpHeaders.acceptEncodingHeader);
-      request.headers.add('dev_fs_name', fsName);
-      request.headers.add('dev_fs_uri_b64', base64.encode(utf8.encode('$deviceUri')));
-      final Stream<List<int>> contents = content.contentsAsCompressedStream();
-      await request.addStream(contents);
-      final HttpClientResponse response = await request.close();
-      await response.drain<void>();
-    } catch (error, trace) {
-      if (!_completer.isCompleted) {
-        printTrace('Error writing "$deviceUri" to DevFS: $error');
-        _completer.completeError(error, trace);
+  }) async {
+    while(true) {
+      try {
+        final HttpClientRequest request = await _client.putUrl(httpAddress);
+        request.headers.removeAll(HttpHeaders.acceptEncodingHeader);
+        request.headers.add('dev_fs_name', fsName);
+        request.headers.add('dev_fs_uri_b64', base64.encode(utf8.encode('$deviceUri')));
+        final Stream<List<int>> contents = content.contentsAsCompressedStream();
+        await request.addStream(contents);
+        final HttpClientResponse response = await request.close();
+        response.listen((_) => null,
+            onError: (dynamic error) { printTrace('error: $error'); },
+            cancelOnError: true);
+        break;
+      } catch (error, trace) {
+        if (!_completer.isCompleted) {
+          printTrace('Error writing "$deviceUri" to DevFS: $error');
+          if (retry > 0) {
+            retry--;
+            printTrace('trying again in a few - $retry more attempts left');
+            await Future<void>.delayed(const Duration(milliseconds: 500));
+            continue;
+          }
+          _completer.completeError(error, trace);
+        }
       }
     }
     _inFlight -= 1;