diff --git a/lib/src/testing/core_matchers.dart b/lib/src/testing/core_matchers.dart
index 502afd1..6ca3388 100644
--- a/lib/src/testing/core_matchers.dart
+++ b/lib/src/testing/core_matchers.dart
@@ -5,6 +5,8 @@
 import 'package:file/file.dart';
 import 'package:test/test.dart';
 
+import 'internal.dart';
+
 /// Matcher that successfully matches against any instance of [Directory].
 const Matcher isDirectory = const isInstanceOf<Directory>();
 
@@ -70,7 +72,14 @@
   final Matcher _matcher;
 
   _FileSystemException(dynamic osErrorCode)
-      : _matcher = osErrorCode == null ? null : wrapMatcher(osErrorCode);
+      : _matcher = _wrapMatcher(osErrorCode);
+
+  static Matcher _wrapMatcher(dynamic osErrorCode) {
+    if (osErrorCode == null) {
+      return null;
+    }
+    return ignoreOsErrorCodes ? anything : wrapMatcher(osErrorCode);
+  }
 
   @override
   bool matches(dynamic item, Map<dynamic, dynamic> matchState) {
diff --git a/lib/src/testing/internal.dart b/lib/src/testing/internal.dart
new file mode 100644
index 0000000..d0cf002
--- /dev/null
+++ b/lib/src/testing/internal.dart
@@ -0,0 +1,9 @@
+// Copyright (c) 2017, the Dart project authors.  Please see the AUTHORS file
+// for details. 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:meta/meta.dart';
+
+/// True if we should ignore OS error codes in our matchers.
+@visibleForTesting
+bool ignoreOsErrorCodes = false;
diff --git a/test/local_test.dart b/test/local_test.dart
index 2b39b66..b8b854c 100644
--- a/test/local_test.dart
+++ b/test/local_test.dart
@@ -6,6 +6,7 @@
 import 'dart:io' as io;
 
 import 'package:file/local.dart';
+import 'package:file/src/testing/internal.dart';
 import 'package:test/test.dart';
 
 import 'common_tests.dart';
@@ -29,89 +30,50 @@
       tmp.deleteSync(recursive: true);
     });
 
+    setUpAll(() {
+      if (io.Platform.isWindows) {
+        // TODO(tvolkert): Remove once all more serious test failures are fixed
+        // https://github.com/google/file.dart/issues/56
+        ignoreOsErrorCodes = true;
+      }
+    });
+
+    tearDownAll(() {
+      ignoreOsErrorCodes = false;
+    });
+
     Map<String, List<String>> skipOnPlatform = <String, List<String>>{
       'windows': <String>[
         'FileSystem > currentDirectory > throwsIfHasNonExistentPathInComplexChain',
         'FileSystem > currentDirectory > staysAtRootIfSetToParentOfRoot',
-        'FileSystem > currentDirectory > throwsIfSetToFilePathSegmentAtTail',
-        'FileSystem > currentDirectory > throwsIfSetToFilePathSegmentViaTraversal',
         'FileSystem > currentDirectory > resolvesLinksIfEncountered',
         'FileSystem > currentDirectory > succeedsIfSetToDirectoryLinkAtTail',
-        'FileSystem > currentDirectory > throwsIfSetToLinkLoop',
         'FileSystem > stat > isFileForLinkToFile',
         'FileSystem > type > isFileForLinkToFileAndFollowLinksTrue',
         'FileSystem > type > isNotFoundForLinkWithCircularReferenceAndFollowLinksTrue',
         'Directory > uri',
         'Directory > exists > falseIfExistsAsLinkToFile',
         'Directory > exists > falseIfNotFoundSegmentExistsThenIsBackedOut',
-        'Directory > create > throwsIfAlreadyExistsAsFile',
         'Directory > create > throwsIfAlreadyExistsAsLinkToFile',
-        'Directory > create > throwsIfAlreadyExistsAsLinkToNotFoundViaTraversal',
-        'Directory > create > throwsIfAncestorDoesntExistRecursiveFalse',
-        'Directory > rename > throwsIfDestinationIsFile',
-        'Directory > rename > throwsIfDestinationParentFolderDoesntExist',
         'Directory > rename > throwsIfDestinationIsNonEmptyDirectory',
-        'Directory > rename > throwsIfSourceIsFile',
-        'Directory > rename > throwsIfDestinationIsLinkToNotFound',
         'Directory > rename > throwsIfDestinationIsLinkToEmptyDirectory',
-        'Directory > delete > throwsIfNonEmptyDirectoryExistsAndRecursiveFalse',
-        'Directory > delete > throwsIfPathReferencesFileAndRecursiveFalse',
         'Directory > delete > throwsIfPathReferencesLinkToFileAndRecursiveFalse',
-        'Directory > delete > throwsIfPathReferencesLinkToNotFoundAndRecursiveFalse',
-        'Directory > resolveSymbolicLinks > throwsIfLoopInLinkChain',
-        'Directory > resolveSymbolicLinks > throwsIfPathNotFoundInTraversal',
         'Directory > resolveSymbolicLinks > throwsIfPathNotFoundInMiddleThenBackedOut',
-        'Directory > createTemp > throwsIfDirectoryDoesntExist',
         'Directory > createTemp > succeedsWithNestedPathPrefixThatExists',
-        'Directory > createTemp > throwsWithNestedPathPrefixThatDoesntExist',
-        'Directory > list > throwsIfDirectoryDoesntExist',
         'Directory > list > followsLinksIfFollowLinksTrue',
         'Directory > list > returnsLinkObjectsForRecursiveLinkIfFollowLinksTrue',
         'File > uri',
-        'File > create > throwsIfAncestorDoesntExistRecursiveFalse',
         'File > create > succeedsIfAlreadyExistsAsLinkToFile',
         'File > create > succeedsIfAlreadyExistsAsLinkToNotFoundAtTail',
-        'File > create > throwsIfAlreadyExistsAsLinkToNotFoundViaTraversal',
         'File > create > succeedsIfAlreadyExistsAsLinkToNotFoundInDifferentDirectory',
-        'File > rename > throwsIfDestinationDoesntExistViaTraversal',
-        'File > rename > throwsIfDestinationExistsAsDirectory',
         'File > rename > succeedsIfDestinationExistsAsLinkToFile',
         'File > rename > succeedsIfDestinationExistsAsLinkToNotFound',
-        'File > rename > throwsIfSourceExistsAsDirectory',
         'File > rename > succeedsIfSourceExistsAsLinkToFile',
-        'File > rename > throwsIfSourceExistsAsLinkToDirectory',
-        'File > copy > throwsIfDestinationDoesntExistViaTraversal',
-        'File > copy > throwsIfDestinationExistsAsDirectory',
         'File > copy > succeedsIfDestinationExistsAsLinkToFile',
-        'File > copy > throwsIfDestinationExistsAsLinkToDirectory',
-        'File > copy > throwsIfSourceExistsAsDirectory',
         'File > copy > succeedsIfSourceExistsAsLinkToFile',
         'File > copy > succeedsIfSourceIsLinkToFileInDifferentDirectory',
         'File > copy > succeedsIfDestinationIsLinkToFileInDifferentDirectory',
-        'File > open > READ > throwsIfDoesntExistViaTraversal',
-        'File > open > READ > RandomAccessFile > throwsIfWriteByte',
-        'File > open > READ > RandomAccessFile > throwsIfWriteFrom',
-        'File > open > READ > RandomAccessFile > throwsIfWriteString',
-        'File > open > READ > RandomAccessFile > position > throwsIfSetToNegativeNumber',
-        'File > open > READ > RandomAccessFile > throwsIfTruncate',
-        'File > open > WRITE > throwsIfDoesntExistViaTraversal',
-        'File > open > WRITE > RandomAccessFile > position > throwsIfSetToNegativeNumber',
-        'File > open > APPEND > throwsIfDoesntExistViaTraversal',
-        'File > open > APPEND > RandomAccessFile > position > throwsIfSetToNegativeNumber',
-        'File > open > WRITE_ONLY > throwsIfDoesntExistViaTraversal',
-        'File > open > WRITE_ONLY > RandomAccessFile > throwsIfReadByte',
-        'File > open > WRITE_ONLY > RandomAccessFile > throwsIfRead',
-        'File > open > WRITE_ONLY > RandomAccessFile > throwsIfReadInto',
-        'File > open > WRITE_ONLY > RandomAccessFile > position > throwsIfSetToNegativeNumber',
-        'File > open > WRITE_ONLY_APPEND > throwsIfDoesntExistViaTraversal',
-        'File > open > WRITE_ONLY_APPEND > RandomAccessFile > throwsIfReadByte',
-        'File > open > WRITE_ONLY_APPEND > RandomAccessFile > throwsIfRead',
-        'File > open > WRITE_ONLY_APPEND > RandomAccessFile > throwsIfReadInto',
-        'File > open > WRITE_ONLY_APPEND > RandomAccessFile > position > throwsIfSetToNegativeNumber',
-        'File > openRead > throwsIfExistsAsDirectory',
         'File > openRead > succeedsIfExistsAsLinkToFile',
-        'File > openWrite > throwsIfExistsAsDirectory',
-        'File > openWrite > throwsIfExistsAsLinkToDirectory',
         'File > openWrite > succeedsIfExistsAsLinkToFile',
         'File > openWrite > ioSink > throwsIfEncodingIsNullAndWriteObject',
         'File > openWrite > ioSink > allowsChangingEncoding',
@@ -127,48 +89,19 @@
         'File > openWrite > ioSink > addStream > blocksCallToWriteCharCodeWhileStreamIsActive',
         'File > openWrite > ioSink > addStream > blocksCallToWritelnWhileStreamIsActive',
         'File > openWrite > ioSink > addStream > blocksCallToFlushWhileStreamIsActive',
-        'File > readAsBytes > throwsIfExistsAsDirectory',
-        'File > readAsBytes > throwsIfExistsAsLinkToDirectory',
         'File > readAsBytes > succeedsIfExistsAsLinkToFile',
-        'File > readAsString > throwsIfExistsAsDirectory',
-        'File > readAsString > throwsIfExistsAsLinkToDirectory',
         'File > readAsString > succeedsIfExistsAsLinkToFile',
-        'File > readAsLines > throwsIfExistsAsDirectory',
-        'File > readAsLines > throwsIfExistsAsLinkToDirectory',
-        'File > writeAsBytes > throwsIfExistsAsDirectory',
-        'File > writeAsBytes > throwsIfExistsAsLinkToDirectory',
         'File > writeAsBytes > succeedsIfExistsAsLinkToFile',
-        'File > writeAsBytes > throwsIfFileModeRead',
-        'File > writeAsString > throwsIfExistsAsDirectory',
-        'File > writeAsString > throwsIfExistsAsLinkToDirectory',
         'File > writeAsString > succeedsIfExistsAsLinkToFile',
-        'File > writeAsString > throwsIfFileModeRead',
         'File > stat > isFileIfExistsAsLinkToFile',
-        'File > delete > throwsIfExistsAsDirectoryAndRecursiveFalse',
         'File > delete > succeedsIfExistsAsLinkToFileAndRecursiveFalse',
-        'File > delete > throwsIfExistsAsLinkToDirectoryAndRecursiveFalse',
         'Link > uri > whenTargetIsDirectory',
         'Link > uri > whenTargetIsFile',
         'Link > uri > whenLinkDoesntExist',
         'Link > stat > isFileIfTargetIsFile',
         'Link > stat > isDirectoryIfTargetIsDirectory',
-        'Link > delete > throwsIfPathReferencesFileAndRecursiveFalse',
-        'Link > delete > throwsIfPathReferencesDirectoryAndRecursiveFalse',
-        'Link > create > throwsIfLinkDoesntExistViaTraversalAndRecursiveFalse',
         'Link > create > succeedsIfLinkDoesntExistViaTraversalAndRecursiveTrue',
-        'Link > create > throwsIfAlreadyExistsAsFile',
-        'Link > create > throwsIfAlreadyExistsAsDirectory',
-        'Link > create > throwsIfAlreadyExistsWithSameTarget',
-        'Link > create > throwsIfAlreadyExistsWithDifferentTarget',
-        'Link > update > throwsIfPathReferencesFile',
-        'Link > update > throwsIfPathReferencesDirectory',
-        'Link > target > throwsIfLinkDoesntExistViaTraversal',
-        'Link > target > throwsIfPathReferencesFile',
-        'Link > target > throwsIfPathReferencesDirectory',
         'Link > rename > returnsCovariantType',
-        'Link > rename > throwsIfSourceIsFile',
-        'Link > rename > throwsIfSourceIsDirectory',
-        'Link > rename > throwsIfDestinationDoesntExistViaTraversal',
         'Link > rename > succeedsIfDestinationExistsAsLinkToFile',
         'Link > rename > throwsIfDestinationExistsAsLinkToDirectory',
         'Link > rename > succeedsIfDestinationExistsAsLinkToNotFound',