diff --git a/packages/flutter_tools/lib/src/base/error_handling_file_system.dart b/packages/flutter_tools/lib/src/base/error_handling_file_system.dart
new file mode 100644
index 0000000000..325cbf63d2
--- /dev/null
+++ b/packages/flutter_tools/lib/src/base/error_handling_file_system.dart
@@ -0,0 +1,241 @@
+// Copyright 2014 The Flutter Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+import 'dart:convert';
+import 'dart:io' as io show Directory, File, Link;
+
+import 'package:file/file.dart';
+import 'package:meta/meta.dart';
+
+import 'common.dart' show throwToolExit;
+import 'platform.dart';
+
+// The Flutter tool hits file system errors that only the end-user can address.
+// We would like these errors to not hit crash logging. In these cases, we
+// should exit gracefully and provide potentially useful advice. For example, if
+// a write fails because the target device is full, we can explain that with a
+// ToolExit and a message that is more clear than the FileSystemException by
+// itself.
+
+/// A [FileSystem] that throws a [ToolExit] on certain errors.
+///
+/// If a [FileSystem] error is not caused by the Flutter tool, and can only be
+/// addressed by the user, it should be caught by this [FileSystem] and thrown
+/// as a [ToolExit] using [throwToolExit].
+///
+/// Cf. If there is some hope that the tool can continue when an operation fails
+/// with an error, then that error/operation should not be handled here. For
+/// example, the tool should gernerally be able to continue executing even if it
+/// fails to delete a file.
+class ErrorHandlingFileSystem extends ForwardingFileSystem {
+  ErrorHandlingFileSystem(FileSystem delegate) : super(delegate);
+
+  @visibleForTesting
+  FileSystem get fileSystem => delegate;
+
+  @override
+  File file(dynamic path) => ErrorHandlingFile(delegate, delegate.file(path));
+}
+
+class ErrorHandlingFile
+    extends ForwardingFileSystemEntity<File, io.File>
+    with ForwardingFile {
+  ErrorHandlingFile(this.fileSystem, this.delegate);
+
+  @override
+  final io.File delegate;
+
+  @override
+  final FileSystem fileSystem;
+
+  @override
+  File wrapFile(io.File delegate) =>
+    ErrorHandlingFile(fileSystem, delegate);
+
+  @override
+  Directory wrapDirectory(io.Directory delegate) =>
+    ErrorHandlingDirectory(fileSystem, delegate);
+
+  @override
+  Link wrapLink(io.Link delegate) =>
+    ErrorHandlingLink(fileSystem, delegate);
+
+  @override
+  Future<File> writeAsBytes(
+    List<int> bytes, {
+    FileMode mode = FileMode.write,
+    bool flush = false,
+  }) async {
+    return _run<File>(
+      () async => wrap(await delegate.writeAsBytes(
+        bytes,
+        mode: mode,
+        flush: flush,
+      )),
+      failureMessage: 'Flutter failed to write to a file at "${delegate.path}"',
+    );
+  }
+
+  @override
+  void writeAsBytesSync(
+    List<int> bytes, {
+    FileMode mode = FileMode.write,
+    bool flush = false,
+  }) {
+    _runSync<void>(
+      () => delegate.writeAsBytesSync(bytes, mode: mode, flush: flush),
+      failureMessage: 'Flutter failed to write to a file at "${delegate.path}"',
+    );
+  }
+
+  @override
+  Future<File> writeAsString(
+    String contents, {
+    FileMode mode = FileMode.write,
+    Encoding encoding = utf8,
+    bool flush = false,
+  }) async {
+    return _run<File>(
+      () async => wrap(await delegate.writeAsString(
+        contents,
+        mode: mode,
+        encoding: encoding,
+        flush: flush,
+      )),
+      failureMessage: 'Flutter failed to write to a file at "${delegate.path}"',
+    );
+  }
+
+  @override
+  void writeAsStringSync(
+    String contents, {
+    FileMode mode = FileMode.write,
+    Encoding encoding = utf8,
+    bool flush = false,
+  }) {
+    _runSync<void>(
+      () => delegate.writeAsStringSync(
+        contents,
+        mode: mode,
+        encoding: encoding,
+        flush: flush,
+      ),
+      failureMessage: 'Flutter failed to write to a file at "${delegate.path}"',
+    );
+  }
+
+  Future<T> _run<T>(Future<T> Function() op, { String failureMessage }) async {
+    try {
+      return await op();
+    } on FileSystemException catch (e) {
+      if (platform.isWindows) {
+        _handleWindowsException(e, failureMessage);
+      }
+      rethrow;
+    }
+  }
+
+  T _runSync<T>(T Function() op, { String failureMessage }) {
+    try {
+      return op();
+    } on FileSystemException catch (e) {
+      if (platform.isWindows) {
+        _handleWindowsException(e, failureMessage);
+      }
+      rethrow;
+    }
+  }
+
+  void _handleWindowsException(FileSystemException e, String message) {
+    // From:
+    // https://docs.microsoft.com/en-us/windows/win32/debug/system-error-codes
+    const int kDeviceFull = 112;
+    const int kUserMappedSectionOpened = 1224;
+    final int errorCode = e.osError?.errorCode ?? 0;
+    // Catch errors and bail when:
+    switch (errorCode) {
+      case kDeviceFull:
+        throwToolExit(
+          '$message. The target device is full.'
+          '\n$e\n'
+          'Free up space and try again.',
+        );
+        break;
+      case kUserMappedSectionOpened:
+        throwToolExit(
+          '$message. The file is being used by another program.'
+          '\n$e\n'
+          'Do you have an antivirus program running? '
+          'Try disabling your antivirus program and try again.',
+        );
+        break;
+      default:
+        // Caller must rethrow the exception.
+        break;
+    }
+  }
+}
+
+class ErrorHandlingDirectory
+    extends ForwardingFileSystemEntity<Directory, io.Directory>
+    with ForwardingDirectory<Directory> {
+  ErrorHandlingDirectory(this.fileSystem, this.delegate);
+
+  @override
+  final io.Directory delegate;
+
+  @override
+  final FileSystem fileSystem;
+
+  @override
+  File wrapFile(io.File delegate) =>
+    ErrorHandlingFile(fileSystem, delegate);
+
+  @override
+  Directory wrapDirectory(io.Directory delegate) =>
+    ErrorHandlingDirectory(fileSystem, delegate);
+
+  @override
+  Link wrapLink(io.Link delegate) =>
+    ErrorHandlingLink(fileSystem, delegate);
+
+  // For the childEntity methods, we first obtain an instance of the entity
+  // from the underlying file system, then invoke childEntity() on it, then
+  // wrap in the ErrorHandling version.
+  @override
+  Directory childDirectory(String basename) =>
+    wrapDirectory(fileSystem.directory(delegate).childDirectory(basename));
+
+  @override
+  File childFile(String basename) =>
+    wrapFile(fileSystem.directory(delegate).childFile(basename));
+
+  @override
+  Link childLink(String basename) =>
+    wrapLink(fileSystem.directory(delegate).childLink(basename));
+}
+
+class ErrorHandlingLink
+    extends ForwardingFileSystemEntity<Link, io.Link>
+    with ForwardingLink {
+  ErrorHandlingLink(this.fileSystem, this.delegate);
+
+  @override
+  final io.Link delegate;
+
+  @override
+  final FileSystem fileSystem;
+
+  @override
+  File wrapFile(io.File delegate) =>
+    ErrorHandlingFile(fileSystem, delegate);
+
+  @override
+  Directory wrapDirectory(io.Directory delegate) =>
+    ErrorHandlingDirectory(fileSystem, delegate);
+
+  @override
+  Link wrapLink(io.Link delegate) =>
+    ErrorHandlingLink(fileSystem, delegate);
+}
diff --git a/packages/flutter_tools/lib/src/base/file_system.dart b/packages/flutter_tools/lib/src/base/file_system.dart
index b8d7bc0f82..b9e927a183 100644
--- a/packages/flutter_tools/lib/src/base/file_system.dart
+++ b/packages/flutter_tools/lib/src/base/file_system.dart
@@ -9,6 +9,7 @@ import 'package:meta/meta.dart';
 
 import 'common.dart' show throwToolExit;
 import 'context.dart';
+import 'error_handling_file_system.dart';
 import 'platform.dart';
 
 export 'package:file/file.dart';
@@ -20,7 +21,9 @@ const FileSystem _kLocalFs = LocalFileSystem();
 ///
 /// By default it uses local disk-based implementation. Override this in tests
 /// with [MemoryFileSystem].
-FileSystem get fs => context.get<FileSystem>() ?? _kLocalFs;
+FileSystem get fs => ErrorHandlingFileSystem(
+  context.get<FileSystem>() ?? _kLocalFs,
+);
 
 /// Create the ancestor directories of a file path if they do not already exist.
 void ensureDirectoryExists(String filePath) {
diff --git a/packages/flutter_tools/test/commands.shard/hermetic/precache_test.dart b/packages/flutter_tools/test/commands.shard/hermetic/precache_test.dart
index 4575ee92b8..d8bc857cc4 100644
--- a/packages/flutter_tools/test/commands.shard/hermetic/precache_test.dart
+++ b/packages/flutter_tools/test/commands.shard/hermetic/precache_test.dart
@@ -174,6 +174,7 @@ void main() {
     FlutterVersion: () => flutterVersion,
     FeatureFlags: () => TestFeatureFlags(isWebEnabled: false),
   });
+
   testUsingContext('precache downloads artifacts when --force is provided', () async {
     when(cache.isUpToDate()).thenReturn(true);
     final PrecacheCommand command = PrecacheCommand();
diff --git a/packages/flutter_tools/test/general.shard/base/error_handling_file_system_test.dart b/packages/flutter_tools/test/general.shard/base/error_handling_file_system_test.dart
new file mode 100644
index 0000000000..1c9e6c9c90
--- /dev/null
+++ b/packages/flutter_tools/test/general.shard/base/error_handling_file_system_test.dart
@@ -0,0 +1,99 @@
+// Copyright 2014 The Flutter Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+import 'package:file/file.dart';
+import 'package:flutter_tools/src/base/error_handling_file_system.dart';
+import 'package:mockito/mockito.dart';
+import 'package:platform/platform.dart';
+
+import '../../src/common.dart';
+import '../../src/context.dart';
+import '../../src/testbed.dart';
+
+class MockFile extends Mock implements File {}
+class MockFileSystem extends Mock implements FileSystem {}
+class MockPlatform extends Mock implements Platform {}
+
+void main() {
+  group('throws ToolExit on Windows', () {
+    const int kDeviceFull = 112;
+    const int kUserMappedSectionOpened = 1224;
+    Testbed testbed;
+    MockFileSystem mockFileSystem;
+    MockPlatform windowsPlatform;
+    ErrorHandlingFileSystem fs;
+
+    setUp(() {
+      mockFileSystem = MockFileSystem();
+      fs = ErrorHandlingFileSystem(mockFileSystem);
+
+      windowsPlatform = MockPlatform();
+      when(windowsPlatform.isWindows).thenReturn(true);
+      when(windowsPlatform.isLinux).thenReturn(false);
+      when(windowsPlatform.isMacOS).thenReturn(false);
+      testbed = Testbed(overrides: <Type, Generator>{
+        Platform: () => windowsPlatform,
+      });
+    });
+
+    void writeTests({
+      String testName,
+      int errorCode,
+      String expectedMessage,
+    }) {
+      test(testName, () => testbed.run(() async {
+        final MockFile mockFile = MockFile();
+        when(mockFileSystem.file(any)).thenReturn(mockFile);
+        when(mockFile.writeAsBytes(
+          any,
+          mode: anyNamed('mode'),
+          flush: anyNamed('flush'),
+        )).thenAnswer((_) async {
+          throw FileSystemException('', '', OSError('', errorCode));
+        });
+        when(mockFile.writeAsString(
+          any,
+          mode: anyNamed('mode'),
+          encoding: anyNamed('encoding'),
+          flush: anyNamed('flush'),
+        )).thenAnswer((_) async {
+          throw FileSystemException('', '', OSError('', errorCode));
+        });
+        when(mockFile.writeAsBytesSync(
+          any,
+          mode: anyNamed('mode'),
+          flush: anyNamed('flush'),
+        )).thenThrow(FileSystemException('', '', OSError('', errorCode)));
+        when(mockFile.writeAsStringSync(
+          any,
+          mode: anyNamed('mode'),
+          encoding: anyNamed('encoding'),
+          flush: anyNamed('flush'),
+        )).thenThrow(FileSystemException('', '', OSError('', errorCode)));
+
+        final File file = fs.file('file');
+
+        expect(() async => await file.writeAsBytes(<int>[0]),
+               throwsToolExit(message: expectedMessage));
+        expect(() async => await file.writeAsString(''),
+               throwsToolExit(message: expectedMessage));
+        expect(() => file.writeAsBytesSync(<int>[0]),
+               throwsToolExit(message: expectedMessage));
+        expect(() => file.writeAsStringSync(''),
+               throwsToolExit(message: expectedMessage));
+      }));
+    }
+
+    writeTests(
+      testName: 'when writing to a full device',
+      errorCode: kDeviceFull,
+      expectedMessage: 'The target device is full',
+    );
+    writeTests(
+      testName: 'when the file is being used by another program',
+      errorCode: kUserMappedSectionOpened,
+      expectedMessage: 'The file is being used by another program',
+    );
+  });
+}
diff --git a/packages/flutter_tools/test/general.shard/forbidden_imports_test.dart b/packages/flutter_tools/test/general.shard/forbidden_imports_test.dart
index babe4260fb..4819c3e1cc 100644
--- a/packages/flutter_tools/test/general.shard/forbidden_imports_test.dart
+++ b/packages/flutter_tools/test/general.shard/forbidden_imports_test.dart
@@ -39,6 +39,7 @@ void main() {
   test('no unauthorized imports of dart:io', () {
     final List<String> whitelistedPaths = <String>[
       fs.path.join(flutterTools, 'lib', 'src', 'base', 'io.dart'),
+      fs.path.join(flutterTools, 'lib', 'src', 'base', 'error_handling_file_system.dart'),
     ];
     bool _isNotWhitelisted(FileSystemEntity entity) => whitelistedPaths.every((String path) => path != entity.path);
 
@@ -83,6 +84,7 @@ void main() {
   test('no unauthorized imports of dart:convert', () {
     final List<String> whitelistedPaths = <String>[
       fs.path.join(flutterTools, 'lib', 'src', 'convert.dart'),
+      fs.path.join(flutterTools, 'lib', 'src', 'base', 'error_handling_file_system.dart'),
     ];
     bool _isNotWhitelisted(FileSystemEntity entity) => whitelistedPaths.every((String path) => path != entity.path);
 
diff --git a/packages/flutter_tools/test/general.shard/runner/flutter_command_test.dart b/packages/flutter_tools/test/general.shard/runner/flutter_command_test.dart
index fa2125e77c..6bd474ffa6 100644
--- a/packages/flutter_tools/test/general.shard/runner/flutter_command_test.dart
+++ b/packages/flutter_tools/test/general.shard/runner/flutter_command_test.dart
@@ -6,6 +6,8 @@ import 'dart:async';
 import 'dart:io' as io;
 
 import 'package:flutter_tools/src/base/common.dart';
+import 'package:flutter_tools/src/base/error_handling_file_system.dart';
+import 'package:flutter_tools/src/base/file_system.dart';
 import 'package:flutter_tools/src/base/io.dart';
 import 'package:flutter_tools/src/base/signals.dart';
 import 'package:flutter_tools/src/base/time.dart';
@@ -65,6 +67,16 @@ void main() {
       Cache: () => cache,
     });
 
+    testUsingContext('uses the error handling file system', () async {
+      final DummyFlutterCommand flutterCommand = DummyFlutterCommand(
+        commandFunction: () async {
+          expect(fs, isA<ErrorHandlingFileSystem>());
+          return const FlutterCommandResult(ExitStatus.success);
+        }
+      );
+      await flutterCommand.run();
+    });
+
     void testUsingCommandContext(String testName, dynamic Function() testBody) {
       testUsingContext(testName, testBody, overrides: <Type, Generator>{
         ProcessInfo: () => mockProcessInfo,
diff --git a/packages/flutter_tools/test/general.shard/testbed_test.dart b/packages/flutter_tools/test/general.shard/testbed_test.dart
index a2d0274cac..7d1c396ecf 100644
--- a/packages/flutter_tools/test/general.shard/testbed_test.dart
+++ b/packages/flutter_tools/test/general.shard/testbed_test.dart
@@ -5,9 +5,11 @@
 import 'dart:async';
 import 'dart:io';
 
+import 'package:file/file.dart';
 import 'package:file/memory.dart';
 import 'package:flutter_tools/src/base/context.dart';
 import 'package:flutter_tools/src/base/file_system.dart';
+import 'package:flutter_tools/src/base/error_handling_file_system.dart';
 
 import '../src/common.dart';
 import '../src/testbed.dart';
@@ -23,7 +25,9 @@ void main() {
         localFileSystem = fs;
       });
 
-      expect(localFileSystem, isA<MemoryFileSystem>());
+      expect(localFileSystem, isA<ErrorHandlingFileSystem>());
+      expect((localFileSystem as ErrorHandlingFileSystem).fileSystem,
+             isA<MemoryFileSystem>());
     });
 
     test('Can provide setup interfaces', () async {