diff --git a/pkgs/io_file/constants.json b/pkgs/io_file/constants.json
index 3635513c..2f05dec5 100644
--- a/pkgs/io_file/constants.json
+++ b/pkgs/io_file/constants.json
@@ -48,5 +48,8 @@
   "<fcntl.h>": [
     "AT_FDCWD",
     "AT_REMOVEDIR"
+  ],
+  "<limits.h>": [
+    "PATH_MAX"
   ]
 }
\ No newline at end of file
diff --git a/pkgs/io_file/dart_test.yaml b/pkgs/io_file/dart_test.yaml
new file mode 100644
index 00000000..f11f1a15
--- /dev/null
+++ b/pkgs/io_file/dart_test.yaml
@@ -0,0 +1,3 @@
+concurrency: 1
+reporter: compact
+test-randomize-ordering-seed: random
diff --git a/pkgs/io_file/lib/src/constant_bindings.g.dart b/pkgs/io_file/lib/src/constant_bindings.g.dart
index bed9de56..d209cf44 100644
--- a/pkgs/io_file/lib/src/constant_bindings.g.dart
+++ b/pkgs/io_file/lib/src/constant_bindings.g.dart
@@ -49,6 +49,9 @@ external int get_AT_FDCWD();
 @ffi.Native<ffi.Int64 Function()>(symbol: 'libc_shim_get_AT_REMOVEDIR')
 external int get_AT_REMOVEDIR();
 
+@ffi.Native<ffi.Int64 Function()>(symbol: 'libc_shim_get_PATH_MAX')
+external int get_PATH_MAX();
+
 @ffi.Native<ffi.Int64 Function()>(symbol: 'libc_shim_get_S_IEXEC')
 external int get_S_IEXEC();
 
diff --git a/pkgs/io_file/lib/src/constants.g.dart b/pkgs/io_file/lib/src/constants.g.dart
index 0c31f77a..dba1e09d 100644
--- a/pkgs/io_file/lib/src/constants.g.dart
+++ b/pkgs/io_file/lib/src/constants.g.dart
@@ -131,6 +131,15 @@ int get AT_REMOVEDIR {
   }
 }
 
+int get PATH_MAX {
+  final v = get_PATH_MAX();
+  if (v == libc_shim_UNDEFINED) {
+    throw UnsupportedError('PATH_MAX');
+  } else {
+    return v;
+  }
+}
+
 int get S_IEXEC {
   final v = get_S_IEXEC();
   if (v == libc_shim_UNDEFINED) {
diff --git a/pkgs/io_file/lib/src/file_system.dart b/pkgs/io_file/lib/src/file_system.dart
index eb815410..a5612754 100644
--- a/pkgs/io_file/lib/src/file_system.dart
+++ b/pkgs/io_file/lib/src/file_system.dart
@@ -86,6 +86,24 @@ base class FileSystem {
     throw UnsupportedError('createTemporaryDirectory');
   }
 
+  /// The current
+  /// [working directory](https://en.wikipedia.org/wiki/Working_directory) of
+  /// the Dart process.
+  ///
+  /// Setting the value of this field will change the working directory for
+  /// *all* isolates.
+  ///
+  /// On Windows, unless
+  /// [long paths are enabled](https://learn.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation),
+  /// the maximum length of the [currentDirectory] path is 260 characters.
+  String get currentDirectory {
+    throw UnsupportedError('currentDirectory');
+  }
+
+  set currentDirectory(String path) {
+    throw UnsupportedError('currentDirectory');
+  }
+
   /// Deletes the directory at the given path.
   ///
   /// If `path` is a directory but the directory is not empty, then
diff --git a/pkgs/io_file/lib/src/libc_bindings.g.dart b/pkgs/io_file/lib/src/libc_bindings.g.dart
index ecfcc5e4..d0fc37bd 100644
--- a/pkgs/io_file/lib/src/libc_bindings.g.dart
+++ b/pkgs/io_file/lib/src/libc_bindings.g.dart
@@ -78,9 +78,17 @@ external ffi.Pointer<ffi.Char> mkdtemp(ffi.Pointer<ffi.Char> template);
 external ffi.Pointer<ffi.Char> strerror(int errnum);
 
 /// <unistd.h>
+@ffi.Native<ffi.Int Function(ffi.Pointer<ffi.Char>)>(symbol: 'libc_shim_chdir')
+external int chdir(ffi.Pointer<ffi.Char> path);
+
 @ffi.Native<ffi.Int Function(ffi.Int)>(symbol: 'libc_shim_close')
 external int close(int fd);
 
+@ffi.Native<ffi.Pointer<ffi.Char> Function(ffi.Pointer<ffi.Char>, ffi.Int64)>(
+  symbol: 'libc_shim_getcwd',
+)
+external ffi.Pointer<ffi.Char> getcwd(ffi.Pointer<ffi.Char> buf, int size);
+
 @ffi.Native<ffi.Int Function(ffi.Int, ffi.Pointer<ffi.Char>, ffi.Int)>(
   symbol: 'libc_shim_unlinkat',
 )
diff --git a/pkgs/io_file/lib/src/vm_posix_file_system.dart b/pkgs/io_file/lib/src/vm_posix_file_system.dart
index 826c12da..bb1dbe9c 100644
--- a/pkgs/io_file/lib/src/vm_posix_file_system.dart
+++ b/pkgs/io_file/lib/src/vm_posix_file_system.dart
@@ -21,7 +21,7 @@ const _defaultMode = 438; // => 0666 => rw-rw-rw-
 /// The default `mode` to use when creating a directory.
 const _defaultDirectoryMode = 511; // => 0777 => rwxrwxrwx
 
-Exception _getError(int err, String message, String path) {
+Exception _getError(int err, String message, [String? path]) {
   //TODO(brianquinlan): In the long-term, do we need to avoid exceptions that
   // are part of `dart:io`? Can we move those exceptions into a different
   // namespace?
@@ -30,12 +30,16 @@ Exception _getError(int err, String message, String path) {
     err,
   );
 
-  if (err == libc.EPERM || err == libc.EACCES) {
-    return io.PathAccessException(path, osError, message);
-  } else if (err == libc.EEXIST) {
-    return io.PathExistsException(path, osError, message);
-  } else if (err == libc.ENOENT) {
-    return io.PathNotFoundException(path, osError, message);
+  if (path != null) {
+    if (err == libc.EPERM || err == libc.EACCES) {
+      return io.PathAccessException(path, osError, message);
+    } else if (err == libc.EEXIST) {
+      return io.PathExistsException(path, osError, message);
+    } else if (err == libc.ENOENT) {
+      return io.PathNotFoundException(path, osError, message);
+    } else {
+      return io.FileSystemException(message, path, osError);
+    }
   } else {
     return io.FileSystemException(message, path, osError);
   }
@@ -95,6 +99,24 @@ base class PosixFileSystem extends FileSystem {
     }
   });
 
+  @override
+  set currentDirectory(String path) => ffi.using((arena) {
+    if (libc.chdir(path.toNativeUtf8(allocator: arena).cast()) == -1) {
+      final errno = libc.errno;
+      throw _getError(errno, 'chdir failed', path);
+    }
+  });
+
+  @override
+  String get currentDirectory => ffi.using((arena) {
+    final buffer = arena<Char>(libc.PATH_MAX);
+    if (libc.getcwd(buffer, libc.PATH_MAX) == nullptr) {
+      final errno = libc.errno;
+      throw _getError(errno, 'getcwd failed', null);
+    }
+    return buffer.cast<ffi.Utf8>().toDartString();
+  });
+
   @override
   String createTemporaryDirectory({String? parent, String? prefix}) =>
       ffi.using((arena) {
diff --git a/pkgs/io_file/lib/src/vm_windows_file_system.dart b/pkgs/io_file/lib/src/vm_windows_file_system.dart
index 8dcfe9a8..101064d5 100644
--- a/pkgs/io_file/lib/src/vm_windows_file_system.dart
+++ b/pkgs/io_file/lib/src/vm_windows_file_system.dart
@@ -23,6 +23,33 @@ void _primeGetLastError() {
   win32.GetLastError();
 }
 
+Pointer<Utf16> _apiPath(String path, Allocator a) =>
+    (r'\\?\' + p.canonicalize(path)).toNativeUtf16(allocator: a);
+
+/*
+Pointer<Utf16> _apiPath(String path, Allocator a) {
+  var length = 256;
+  var utf16Path = path.toNativeUtf16(allocator: a);
+  do {
+    final buffer = win32.wsalloc(length);
+    try {
+      final result = win32.GetFullPathName(utf16Path, length, buffer, nullptr);
+      if (result == 0) {
+        final errorCode = win32.GetLastError();
+        throw _getError(errorCode, 'GetFullPathName failed', path);
+      }
+      if (result < length) {
+        win32.PathAllocCanonicalize()
+      } else {
+        length = result;
+      }
+    } finally {
+      win32.free(buffer);
+    }
+  } while (true);
+}
+*/
+
 String _formatMessage(int errorCode) {
   final buffer = win32.wsalloc(1024);
   try {
@@ -130,8 +157,7 @@ base class WindowsFileSystem extends FileSystem {
   void createDirectory(String path) => using((arena) {
     _primeGetLastError();
 
-    if (win32.CreateDirectory(path.toNativeUtf16(allocator: arena), nullptr) ==
-        win32.FALSE) {
+    if (win32.CreateDirectory(_apiPath(path, arena), nullptr) == win32.FALSE) {
       final errorCode = win32.GetLastError();
       throw _getError(errorCode, 'create directory failed', path);
     }
@@ -148,6 +174,44 @@ base class WindowsFileSystem extends FileSystem {
     return path;
   }
 
+  @override
+  set currentDirectory(String path) => using((arena) {
+    // XXX
+    // SetCurrentDirectory does not actually support paths larger than MAX_PATH,
+    // this limitation is due to the size of the internal buffer used for
+    // storing
+    // current directory. In Windows 10, version 1607, changes have been made
+    // to the OS to lift MAX_PATH limitations from file and directory management
+    // APIs, but both application and OS need to opt-in into new behavior.
+    // See https://learn.microsoft.com/en-us/windows/win32/fileio/maximum-file-path-limitation?tabs=registry#enable-long-paths-in-windows-10-version-1607-and-later
+
+    _primeGetLastError();
+    if (win32.SetCurrentDirectory(path.toNativeUtf16()) == win32.FALSE) {
+      final errorCode = win32.GetLastError();
+      throw _getError(errorCode, 'SetCurrentDirectory failed', path);
+    }
+  });
+
+  @override
+  String get currentDirectory => using((arena) {
+    _primeGetLastError();
+
+    var length = 256;
+    do {
+      final buffer = win32.wsalloc(length);
+      try {
+        final result = win32.GetCurrentDirectory(length, buffer);
+        if (result < length) {
+          return buffer.toDartString();
+        } else {
+          length = result;
+        }
+      } finally {
+        win32.free(buffer);
+      }
+    } while (true);
+  });
+
   @override
   void removeDirectory(String path) => using((arena) {
     _primeGetLastError();
@@ -247,7 +311,7 @@ base class WindowsFileSystem extends FileSystem {
     _primeGetLastError();
 
     final f = win32.CreateFile(
-      path.toNativeUtf16(),
+      _apiPath(path, arena),
       win32.GENERIC_READ | win32.FILE_SHARE_READ,
       win32.FILE_SHARE_READ | win32.FILE_SHARE_WRITE,
       nullptr,
@@ -383,7 +447,7 @@ base class WindowsFileSystem extends FileSystem {
     };
 
     final f = win32.CreateFile(
-      path.toNativeUtf16(allocator: arena),
+      _apiPath(path, arena),
       mode == WriteMode.appendExisting
           ? win32.FILE_APPEND_DATA
           : win32.FILE_GENERIC_WRITE,
diff --git a/pkgs/io_file/pubspec.yaml b/pkgs/io_file/pubspec.yaml
index d5ed591d..b8a29f7b 100644
--- a/pkgs/io_file/pubspec.yaml
+++ b/pkgs/io_file/pubspec.yaml
@@ -14,7 +14,7 @@ dependencies:
   logging: ^1.3.0
   native_toolchain_c: ^0.16.0
   path: ^1.9.1
-  win32: ^5.11.0
+  win32: ^5.13.0
 
 dev_dependencies:
   args: ^2.7.0
diff --git a/pkgs/io_file/src/constants.g.c b/pkgs/io_file/src/constants.g.c
index 07f52f40..7eb9de23 100644
--- a/pkgs/io_file/src/constants.g.c
+++ b/pkgs/io_file/src/constants.g.c
@@ -7,6 +7,7 @@
 
 #include <errno.h>
 #include <fcntl.h>
+#include <limits.h>
 #include <sys/stat.h>
 int64_t libc_shim_get_EACCES(void) {
 #ifdef EACCES
@@ -106,6 +107,13 @@ int64_t libc_shim_get_AT_REMOVEDIR(void) {
 #endif
   return libc_shim_UNDEFINED;
 }
+int64_t libc_shim_get_PATH_MAX(void) {
+#ifdef PATH_MAX
+  assert(PATH_MAX != libc_shim_UNDEFINED);
+  return PATH_MAX;
+#endif
+  return libc_shim_UNDEFINED;
+}
 int64_t libc_shim_get_S_IEXEC(void) {
 #ifdef S_IEXEC
   assert(S_IEXEC != libc_shim_UNDEFINED);
diff --git a/pkgs/io_file/src/constants.g.h b/pkgs/io_file/src/constants.g.h
index 2d724b4c..780c0c7b 100644
--- a/pkgs/io_file/src/constants.g.h
+++ b/pkgs/io_file/src/constants.g.h
@@ -38,6 +38,8 @@ int64_t libc_shim_get_AT_FDCWD(void);
 __attribute__((visibility("default"))) __attribute__((used))
 int64_t libc_shim_get_AT_REMOVEDIR(void);
 __attribute__((visibility("default"))) __attribute__((used))
+int64_t libc_shim_get_PATH_MAX(void);
+__attribute__((visibility("default"))) __attribute__((used))
 int64_t libc_shim_get_S_IEXEC(void);
 __attribute__((visibility("default"))) __attribute__((used))
 int64_t libc_shim_get_S_IFBLK(void);
diff --git a/pkgs/io_file/src/libc_shim.c b/pkgs/io_file/src/libc_shim.c
index ac86db45..41eaf6a5 100644
--- a/pkgs/io_file/src/libc_shim.c
+++ b/pkgs/io_file/src/libc_shim.c
@@ -142,8 +142,12 @@ char *libc_shim_strerror(int errnum) { return strerror(errnum); }
 
 // <unistd.h>
 
+int libc_shim_chdir(const char *path) { return chdir(path); }
+
 int libc_shim_close(int fd) { return close(fd); }
 
+char *libc_shim_getcwd(char *buf, int64_t size) { return getcwd(buf, size); }
+
 int libc_shim_unlinkat(int dirfd, const char *pathname, int flags) {
   return unlinkat(dirfd, pathname, flags);
 }
diff --git a/pkgs/io_file/src/libc_shim.h b/pkgs/io_file/src/libc_shim.h
index 0ebe26b5..a2a89924 100644
--- a/pkgs/io_file/src/libc_shim.h
+++ b/pkgs/io_file/src/libc_shim.h
@@ -106,6 +106,8 @@ LIBC_SHIM_EXPORT char *libc_shim_strerror(int errnum);
 
 // <unistd.h>
 
+LIBC_SHIM_EXPORT int libc_shim_chdir(const char *path);
 LIBC_SHIM_EXPORT int libc_shim_close(int fd);
+LIBC_SHIM_EXPORT char *libc_shim_getcwd(char *buf, int64_t size);
 LIBC_SHIM_EXPORT int libc_shim_unlinkat(int dirfd, const char *pathname,
                                         int flags);
diff --git a/pkgs/io_file/test/create_directory_test.dart b/pkgs/io_file/test/create_directory_test.dart
index fb0f8672..cff3e883 100644
--- a/pkgs/io_file/test/create_directory_test.dart
+++ b/pkgs/io_file/test/create_directory_test.dart
@@ -8,6 +8,7 @@ library;
 import 'dart:io';
 
 import 'package:io_file/io_file.dart';
+import 'package:path/path.dart' as p;
 import 'package:test/test.dart';
 import 'package:win32/win32.dart' as win32;
 
@@ -17,12 +18,18 @@ import 'test_utils.dart';
 void main() {
   group('createDirectory', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('createDirectory'));
-
-    tearDown(() => deleteTemp(tmp));
+    setUp(() {
+      tmp = createTemp('createDirectory');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    //TODO(brianquinlan): test with a very long path.
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     test('success', () {
       final path = '$tmp/dir';
@@ -31,6 +38,75 @@ void main() {
       expect(FileSystemEntity.isDirectorySync(path), isTrue);
     });
 
+    test('absolute path, long directory name', () {
+      // On Windows:
+      // When using an API to create a directory, the specified path cannot be
+      // so long that you cannot append an 8.3 file name (that is, the directory
+      // name cannot exceed MAX_PATH minus 12).
+      final dirname = ''.padLeft(
+        Platform.isWindows ? win32.MAX_PATH - 12 : 255,
+        'd',
+      );
+      final path = p.join(tmp, dirname);
+
+      fileSystem.createDirectory(path);
+      expect(FileSystemEntity.isDirectorySync(path), isTrue);
+    });
+
+    test('absolute path, too long directory name', () {
+      final path = p.join(tmp, ''.padRight(256, 'd'));
+
+      expect(
+        () => fileSystem.createDirectory(path),
+        throwsA(
+          isA<FileSystemException>()
+              .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
+              .having(
+                (e) => e.osError?.errorCode,
+                'errorCode',
+                Platform.isWindows
+                    ? win32.ERROR_INVALID_NAME
+                    : errors.enametoolong,
+              ),
+        ),
+      );
+    });
+
+    test('relative path, long directory name', () {
+      // On Windows:
+      // When using an API to create a directory, the specified path cannot be
+      // so long that you cannot append an 8.3 file name (that is, the directory
+      // name cannot exceed MAX_PATH minus 12).
+      final path = ''.padLeft(
+        Platform.isWindows ? win32.MAX_PATH - 12 : 255,
+        'd',
+      );
+      fileSystem.createDirectory(path);
+
+      expect(FileSystemEntity.isDirectorySync(path), isTrue);
+    });
+
+    test('relative path, too long directory name', () {
+      final path = ''.padRight(256, 'd');
+
+      expect(
+        () => fileSystem.createDirectory(path),
+        throwsA(
+          isA<FileSystemException>()
+              .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
+              .having(
+                (e) => e.osError?.errorCode,
+                'errorCode',
+                Platform.isWindows
+                    ? win32.ERROR_INVALID_NAME
+                    : errors.enametoolong,
+              ),
+        ),
+      );
+    });
+
     test('create in non-existent directory', () {
       final path = '$tmp/foo/dir';
 
@@ -39,6 +115,7 @@ void main() {
         throwsA(
           isA<PathNotFoundException>()
               .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
               .having(
                 (e) => e.osError?.errorCode,
                 'errorCode',
@@ -57,6 +134,41 @@ void main() {
         throwsA(
           isA<PathExistsException>()
               .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
+              .having(
+                (e) => e.osError?.errorCode,
+                'errorCode',
+                Platform.isWindows ? win32.ERROR_ALREADY_EXISTS : errors.eexist,
+              ),
+        ),
+      );
+    });
+
+    test('create "."', () {
+      const path = '.';
+      expect(
+        () => fileSystem.createDirectory(path),
+        throwsA(
+          isA<PathExistsException>()
+              .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
+              .having(
+                (e) => e.osError?.errorCode,
+                'errorCode',
+                Platform.isWindows ? win32.ERROR_ALREADY_EXISTS : errors.eexist,
+              ),
+        ),
+      );
+    });
+
+    test('create ".."', () {
+      const path = '..';
+      expect(
+        () => fileSystem.createDirectory(path),
+        throwsA(
+          isA<PathExistsException>()
+              .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
               .having(
                 (e) => e.osError?.errorCode,
                 'errorCode',
@@ -75,6 +187,7 @@ void main() {
         throwsA(
           isA<PathExistsException>()
               .having((e) => e.message, 'message', 'create directory failed')
+              .having((e) => e.path, 'path', path)
               .having(
                 (e) => e.osError?.errorCode,
                 'errorCode',
diff --git a/pkgs/io_file/test/create_temporary_directory_test.dart b/pkgs/io_file/test/create_temporary_directory_test.dart
index 1df8ef1e..031b190f 100644
--- a/pkgs/io_file/test/create_temporary_directory_test.dart
+++ b/pkgs/io_file/test/create_temporary_directory_test.dart
@@ -18,12 +18,18 @@ import 'test_utils.dart';
 void main() {
   group('createTemporaryDirectory', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('createTemporaryDirectory'));
-
-    tearDown(() => deleteTemp(tmp));
+    setUp(() {
+      tmp = createTemp('createTemporaryDirectory');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    //TODO(brianquinlan): test with a very long path.
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     test('no arguments', () {
       final tmp1 = fileSystem.createTemporaryDirectory();
diff --git a/pkgs/io_file/test/current_directory_test.dart b/pkgs/io_file/test/current_directory_test.dart
new file mode 100644
index 00000000..34f0d53f
--- /dev/null
+++ b/pkgs/io_file/test/current_directory_test.dart
@@ -0,0 +1,96 @@
+// Copyright (c) 2025, 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.
+
+@TestOn('vm')
+library;
+
+import 'dart:io';
+
+import 'package:io_file/io_file.dart';
+import 'package:path/path.dart' as p;
+import 'package:test/test.dart';
+import 'package:win32/win32.dart' as win32;
+
+import 'test_utils.dart';
+
+void main() {
+  group('currentDirectory', () {
+    late String tmp;
+    late String cwd;
+
+    setUp(() {
+      tmp = createTemp('currentDirectory');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
+
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
+
+    //TODO(brianquinlan): test with a very long path.
+
+    test('absolute path', () {
+      final path = '$tmp/dir';
+      Directory(path).createSync(recursive: true);
+
+      fileSystem.currentDirectory = path;
+
+      expect(
+        fileSystem.same(fileSystem.currentDirectory, path),
+        isTrue,
+        reason:
+            '${fileSystem.currentDirectory} is a diffent directory than'
+            '$path',
+      );
+      expect(
+        p.isAbsolute(fileSystem.currentDirectory),
+        isTrue,
+        reason: '${fileSystem.currentDirectory} is not absolute',
+      );
+    });
+
+    test('absolute path, too long path', () {
+      // On Windows, limited to MAX_PATH (260) characters.
+      final path = p.join(tmp, ''.padLeft(200, 'a'), ''.padLeft(200, 'b'));
+      Directory(path).createSync(recursive: true);
+      final oldCurrentDirectory = fileSystem.currentDirectory;
+
+      expect(
+        () => fileSystem.currentDirectory = path,
+        throwsA(
+          isA<FileSystemException>()
+              .having((e) => e.path, 'path', path)
+              .having(
+                (e) => e.osError?.errorCode,
+                'errorCode',
+                win32.ERROR_FILENAME_EXCED_RANGE,
+              ),
+        ),
+      );
+      expect(fileSystem.currentDirectory, oldCurrentDirectory);
+    }, skip: !Platform.isWindows);
+
+    test('relative path', () {
+      final path = '$tmp/dir';
+      Directory(path).createSync(recursive: true);
+
+      fileSystem.currentDirectory = 'dir';
+
+      expect(
+        fileSystem.same(fileSystem.currentDirectory, path),
+        isTrue,
+        reason:
+            '${fileSystem.currentDirectory} is a diffent directory than '
+            '$path',
+      );
+      expect(
+        p.isAbsolute(fileSystem.currentDirectory),
+        isTrue,
+        reason: '${fileSystem.currentDirectory} is not absolute',
+      );
+    });
+  });
+}
diff --git a/pkgs/io_file/test/errors.dart b/pkgs/io_file/test/errors.dart
index 77a630f6..0c70a3eb 100644
--- a/pkgs/io_file/test/errors.dart
+++ b/pkgs/io_file/test/errors.dart
@@ -9,6 +9,9 @@ int get eexist => Platform.isMacOS ? DarwinErrors.eexist : LinuxErrors.eexist;
 
 int get eisdir => Platform.isMacOS ? DarwinErrors.eisdir : LinuxErrors.eisdir;
 
+int get enametoolong =>
+    Platform.isMacOS ? DarwinErrors.enametoolong : LinuxErrors.enametoolong;
+
 int get enoent => Platform.isMacOS ? DarwinErrors.enoent : LinuxErrors.enoent;
 
 int get enotdir =>
diff --git a/pkgs/io_file/test/read_as_bytes_test.dart b/pkgs/io_file/test/read_as_bytes_test.dart
index 858efe35..b65798c3 100644
--- a/pkgs/io_file/test/read_as_bytes_test.dart
+++ b/pkgs/io_file/test/read_as_bytes_test.dart
@@ -10,6 +10,7 @@ import 'dart:typed_data';
 
 import 'package:io_file/io_file.dart';
 import 'package:io_file/src/internal_constants.dart';
+import 'package:path/path.dart' as p;
 import 'package:test/test.dart';
 import 'package:win32/win32.dart' as win32;
 
@@ -22,10 +23,18 @@ void main() {
 
   group('readAsBytes', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('readAsBytes'));
+    setUp(() {
+      tmp = createTemp('readAsBytes');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    tearDown(() => deleteTemp(tmp));
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     test('non-existant file', () {
       expect(
@@ -136,6 +145,16 @@ void main() {
       }
     });
     group('regular files', () {
+      test('absolute path, long file name', () {
+        final data = randomUint8List(20);
+        final subdir = p.join(tmp, ''.padRight(255, 'f'));
+        final path = '$subdir/file';
+        Directory(subdir).createSync();
+
+        File(path).writeAsBytesSync(data);
+        expect(fileSystem.readAsBytes(path), data);
+      });
+
       for (var i = 0; i <= 1024; ++i) {
         test('Read small file: $i bytes', () {
           final data = randomUint8List(i);
diff --git a/pkgs/io_file/test/remove_directory_test.dart b/pkgs/io_file/test/remove_directory_test.dart
index 7be6ba5b..431e6c22 100644
--- a/pkgs/io_file/test/remove_directory_test.dart
+++ b/pkgs/io_file/test/remove_directory_test.dart
@@ -17,10 +17,18 @@ import 'test_utils.dart';
 void main() {
   group('removeDirectory', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('removeDirectory'));
+    setUp(() {
+      tmp = createTemp('removeDirectory');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    tearDown(() => deleteTemp(tmp));
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     //TODO(brianquinlan): test with a very long path.
 
diff --git a/pkgs/io_file/test/remove_directory_tree_test.dart b/pkgs/io_file/test/remove_directory_tree_test.dart
index 370a3f98..7f34c8a4 100644
--- a/pkgs/io_file/test/remove_directory_tree_test.dart
+++ b/pkgs/io_file/test/remove_directory_tree_test.dart
@@ -17,10 +17,18 @@ import 'test_utils.dart';
 void main() {
   group('removeDirectoryTree', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('removeDirectoryTree'));
+    setUp(() {
+      tmp = createTemp('removeDirectoryTree');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    tearDown(() => deleteTemp(tmp));
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     //TODO(brianquinlan): test with a very long path.
 
diff --git a/pkgs/io_file/test/rename_test.dart b/pkgs/io_file/test/rename_test.dart
index 4deef9b6..8d22f4e0 100644
--- a/pkgs/io_file/test/rename_test.dart
+++ b/pkgs/io_file/test/rename_test.dart
@@ -13,12 +13,20 @@ import 'package:test/test.dart';
 import 'test_utils.dart';
 
 void main() {
-  group('move', () {
+  group('rename', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('move'));
+    setUp(() {
+      tmp = createTemp('rename');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    tearDown(() => deleteTemp(tmp));
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     //TODO(brianquinlan): test with a very long path.
 
diff --git a/pkgs/io_file/test/same_test.dart b/pkgs/io_file/test/same_test.dart
index 9f296b81..d31b8ee7 100644
--- a/pkgs/io_file/test/same_test.dart
+++ b/pkgs/io_file/test/same_test.dart
@@ -18,20 +18,19 @@ import 'test_utils.dart';
 void main() {
   group('same', () {
     late String tmp;
-    late Directory cwd;
+    late String cwd;
 
     setUp(() {
       tmp = createTemp('same');
-      cwd = Directory.current;
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
     });
 
     tearDown(() {
-      Directory.current = cwd;
+      fileSystem.currentDirectory = cwd;
       deleteTemp(tmp);
     });
 
-    //TODO(brianquinlan): test with a very long path.
-
     test('path1 does not exist', () {
       final path1 = '$tmp/file1';
       final path2 = '$tmp/file2';
@@ -157,7 +156,7 @@ void main() {
     });
 
     test('same file, absolute and relative paths', () {
-      Directory.current = tmp;
+      fileSystem.currentDirectory = tmp;
       final path1 = '$tmp/file1';
       const path2 = 'file1';
       File(path1).writeAsStringSync('Hello World');
@@ -216,7 +215,6 @@ void main() {
     });
 
     test('same directory, absolute and relative paths', () {
-      Directory.current = tmp;
       final path1 = '$tmp/dir1';
       const path2 = 'dir1';
       Directory(path1).createSync();
diff --git a/pkgs/io_file/test/write_as_bytes_test.dart b/pkgs/io_file/test/write_as_bytes_test.dart
index ce479db2..844483c7 100644
--- a/pkgs/io_file/test/write_as_bytes_test.dart
+++ b/pkgs/io_file/test/write_as_bytes_test.dart
@@ -9,6 +9,7 @@ import 'dart:io';
 import 'dart:typed_data';
 
 import 'package:io_file/io_file.dart';
+import 'package:path/path.dart' as p;
 import 'package:test/test.dart';
 import 'package:win32/win32.dart' as win32;
 
@@ -16,14 +17,20 @@ import 'errors.dart' as errors;
 import 'test_utils.dart';
 
 void main() {
-  //TODO(brianquinlan): test with a very long path.
-
   group('writeAsBytes', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('writeAsBytes'));
+    setUp(() {
+      tmp = createTemp('writeAsBytes');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    tearDown(() => deleteTemp(tmp));
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     test('directory', () {
       expect(
@@ -204,6 +211,16 @@ void main() {
       });
     });
 
+    test('absolute path, long file name', () {
+      final data = randomUint8List(20);
+      final subdir = p.join(tmp, ''.padRight(255, 'f'));
+      final path = '$subdir/file';
+      Directory(subdir).createSync();
+
+      fileSystem.writeAsBytes(path, data, WriteMode.truncateExisting);
+      expect(File(path).readAsBytesSync(), data);
+    });
+
     group('regular files', () {
       for (var i = 0; i <= 1024; ++i) {
         test('Write small file: $i bytes', () {
diff --git a/pkgs/io_file/test/write_as_string_test.dart b/pkgs/io_file/test/write_as_string_test.dart
index c6b5a12a..c3c3cc0e 100644
--- a/pkgs/io_file/test/write_as_string_test.dart
+++ b/pkgs/io_file/test/write_as_string_test.dart
@@ -10,6 +10,7 @@ import 'dart:io';
 import 'dart:typed_data';
 
 import 'package:io_file/io_file.dart';
+import 'package:path/path.dart' as p;
 import 'package:test/test.dart';
 import 'package:win32/win32.dart' as win32;
 
@@ -21,10 +22,18 @@ void main() {
 
   group('writeAsString', () {
     late String tmp;
+    late String cwd;
 
-    setUp(() => tmp = createTemp('writeAsString'));
+    setUp(() {
+      tmp = createTemp('writeAsString');
+      cwd = fileSystem.currentDirectory;
+      fileSystem.currentDirectory = tmp;
+    });
 
-    tearDown(() => deleteTemp(tmp));
+    tearDown(() {
+      fileSystem.currentDirectory = cwd;
+      deleteTemp(tmp);
+    });
 
     test('directory', () {
       expect(
@@ -204,6 +213,15 @@ void main() {
       });
     });
 
+    test('absolute path, long file name', () {
+      final subdir = p.join(tmp, ''.padRight(255, 'f'));
+      final path = '$subdir/file';
+      Directory(subdir).createSync();
+
+      fileSystem.writeAsString(path, 'Hello World!');
+      expect(File(path).readAsStringSync(), 'Hello World!');
+    });
+
     group('encoding', () {
       test('non-ascii', () {
         final path = '$tmp/file';