diff --git a/pkg/test_runner/lib/src/options.dart b/pkg/test_runner/lib/src/options.dart
index cc534cabd0f..5c991eab1a0 100644
--- a/pkg/test_runner/lib/src/options.dart
+++ b/pkg/test_runner/lib/src/options.dart
@@ -637,6 +637,11 @@ has been specified on the command line.''')
     var progress = Progress.find(data["progress"] as String);
     var nnbdMode = NnbdMode.find(data["nnbd"] as String);
 
+    // TODO: deflaking should report logs.
+    if (data['repeat'] == 5) {
+      progress = Progress.verbose;
+    }
+
     void addConfiguration(Configuration innerConfiguration,
         [String? namedConfiguration]) {
       var configuration = TestConfiguration(
diff --git a/runtime/bin/directory.h b/runtime/bin/directory.h
index 3226e387ada..43904b753ba 100644
--- a/runtime/bin/directory.h
+++ b/runtime/bin/directory.h
@@ -242,6 +242,11 @@ class Directory {
   enum ExistsResult { UNKNOWN, EXISTS, DOES_NOT_EXIST };
 
   static void List(DirectoryListing* listing);
+
+#if defined(DART_HOST_OS_WINDOWS)
+  static ExistsResult Exists(const wchar_t* path);
+#endif
+
   static ExistsResult Exists(Namespace* namespc, const char* path);
 
   // Returns the current working directory. The caller must call
diff --git a/runtime/bin/directory_win.cc b/runtime/bin/directory_win.cc
index db4ec43cff3..0fd6c77aefd 100644
--- a/runtime/bin/directory_win.cc
+++ b/runtime/bin/directory_win.cc
@@ -47,8 +47,8 @@ const char* PathBuffer::AsScopedString() const {
 }
 
 bool PathBuffer::Add(const char* name) {
-  Utf8ToWideScope wide_name(name);
-  return AddW(wide_name.wide());
+  const auto wide_name = Utf8ToWideChar(name);
+  return AddW(wide_name.get());
 }
 
 bool PathBuffer::AddW(const wchar_t* name) {
@@ -228,114 +228,137 @@ void DirectoryListingEntry::ResetLink() {
   }
 }
 
-static bool DeleteFile(const wchar_t* file_name, PathBuffer* path) {
-  if (!path->AddW(file_name)) {
-    return false;
+namespace {
+class RecursiveDeleter {
+ public:
+  RecursiveDeleter() : path_() {}
+
+  // Delete the given directory recursively. Expects an absolute long prefixed
+  // path - which allows deletion to proceed without checking if path needs to
+  // be prefixed while recursing.
+  bool DeleteRecursively(const std::unique_ptr<wchar_t[]>& path) {
+    ASSERT(wcsncmp(path.get(), L"\\\\?\\", 4) == 0);
+    path_.Reset(0);
+    if (path == nullptr || !path_.AddW(path.get()) || path_.length() == 0) {
+      return false;
+    }
+
+    if (path_.AsStringW()[path_.length() - 1] == '\\') {
+      // Strip trailing slash otherwise FindFirstFileW will fail.
+      path_.Reset(path_.length() - 1);
+    }
+
+    return DeleteDirectory();
   }
 
-  if (DeleteFileW(path->AsStringW()) != 0) {
-    return true;
-  }
+ private:
+  const wchar_t* path() const { return path_.AsStringW(); }
 
-  // If we failed because the file is read-only, make it writeable and try
-  // again. This mirrors Linux/Mac where a directory containing read-only files
-  // can still be recursively deleted.
-  if (GetLastError() == ERROR_ACCESS_DENIED) {
-    DWORD attributes = GetFileAttributesW(path->AsStringW());
+  bool DeleteDirectory() {
+    DWORD attributes = GetFileAttributesW(path());
     if (attributes == INVALID_FILE_ATTRIBUTES) {
       return false;
     }
 
-    if ((attributes & FILE_ATTRIBUTE_READONLY) == FILE_ATTRIBUTE_READONLY) {
-      attributes &= ~FILE_ATTRIBUTE_READONLY;
+    // If the directory is a junction, it's pointing to some other place in the
+    // filesystem that we do not want to recurse into.
+    if ((attributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0) {
+      // Just delete the junction itself.
+      return RemoveDirectoryW(path()) != 0;
+    }
 
-      if (SetFileAttributesW(path->AsStringW(), attributes) == 0) {
+    // If it's a file, remove it directly.
+    if ((attributes & FILE_ATTRIBUTE_DIRECTORY) == 0) {
+      return DeleteFile();
+    }
+
+    if (!path_.AddW(L"\\*")) {
+      return false;
+    }
+
+    WIN32_FIND_DATAW find_file_data;
+    HANDLE find_handle = FindFirstFileW(path(), &find_file_data);
+
+    if (find_handle == INVALID_HANDLE_VALUE) {
+      return false;
+    }
+
+    // Adjust the path by removing the '*' used for the search.
+    const int path_length = path_.length() - 1;
+    path_.Reset(path_length);
+
+    do {
+      if (!DeleteEntry(&find_file_data)) {
+        break;
+      }
+      path_.Reset(path_length);  // DeleteEntry adds to the path.
+    } while (FindNextFileW(find_handle, &find_file_data) != 0);
+
+    DWORD last_error = GetLastError();
+    // Always close handle.
+    FindClose(find_handle);
+    if (last_error != ERROR_NO_MORE_FILES) {
+      // Unexpected error, set and return.
+      SetLastError(last_error);
+      return false;
+    }
+    // All content deleted successfully, try to delete directory.
+    // Drop the "\" from the end of the path.
+    path_.Reset(path_length - 1);
+    return RemoveDirectoryW(path()) != 0;
+  }
+
+  bool DeleteEntry(LPWIN32_FIND_DATAW find_file_data) {
+    wchar_t* entry_name = find_file_data->cFileName;
+    if ((wcscmp(entry_name, L".") == 0) || (wcscmp(entry_name, L"..") == 0)) {
+      return true;
+    }
+
+    if (!path_.AddW(entry_name)) {
+      return false;
+    }
+
+    DWORD attributes = find_file_data->dwFileAttributes;
+    if ((attributes & FILE_ATTRIBUTE_DIRECTORY) != 0) {
+      return DeleteDirectory();
+    } else {
+      return DeleteFile();
+    }
+  }
+
+  bool DeleteFile() {
+    if (DeleteFileW(path()) != 0) {
+      return true;
+    }
+
+    // If we failed because the file is read-only, make it writeable and try
+    // again. This mirrors Linux/Mac where a directory containing read-only
+    // files can still be recursively deleted.
+    if (GetLastError() == ERROR_ACCESS_DENIED) {
+      DWORD attributes = GetFileAttributesW(path());
+      if (attributes == INVALID_FILE_ATTRIBUTES) {
         return false;
       }
 
-      return DeleteFileW(path->AsStringW()) != 0;
+      if ((attributes & FILE_ATTRIBUTE_READONLY) == FILE_ATTRIBUTE_READONLY) {
+        attributes &= ~FILE_ATTRIBUTE_READONLY;
+
+        if (SetFileAttributesW(path(), attributes) == 0) {
+          return false;
+        }
+
+        return DeleteFileW(path()) != 0;
+      }
     }
-  }
 
-  return false;
-}
-
-static bool DeleteDir(const wchar_t* dir_name, PathBuffer* path) {
-  if ((wcscmp(dir_name, L".") == 0) || (wcscmp(dir_name, L"..") == 0)) {
-    return true;
-  }
-  return path->AddW(dir_name) && DeleteRecursively(path);
-}
-
-static bool DeleteEntry(LPWIN32_FIND_DATAW find_file_data, PathBuffer* path) {
-  DWORD attributes = find_file_data->dwFileAttributes;
-
-  if ((attributes & FILE_ATTRIBUTE_DIRECTORY) != 0) {
-    return DeleteDir(find_file_data->cFileName, path);
-  } else {
-    return DeleteFile(find_file_data->cFileName, path);
-  }
-}
-
-static bool DeleteRecursively(PathBuffer* path) {
-  PathBuffer prefixed_path;
-  if (!prefixed_path.Add(PrefixLongDirectoryPath(path->AsScopedString()))) {
     return false;
   }
 
-  DWORD attributes = GetFileAttributesW(prefixed_path.AsStringW());
-  if (attributes == INVALID_FILE_ATTRIBUTES) {
-    return false;
-  }
-  // If the directory is a junction, it's pointing to some other place in the
-  // filesystem that we do not want to recurse into.
-  if ((attributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0) {
-    // Just delete the junction itself.
-    return RemoveDirectoryW(prefixed_path.AsStringW()) != 0;
-  }
-  // If it's a file, remove it directly.
-  if ((attributes & FILE_ATTRIBUTE_DIRECTORY) == 0) {
-    return DeleteFile(L"", &prefixed_path);
-  }
+  PathBuffer path_;
+};
+}  // namespace
 
-  if (!prefixed_path.AddW(L"\\*")) {
-    return false;
-  }
-
-  WIN32_FIND_DATAW find_file_data;
-  HANDLE find_handle =
-      FindFirstFileW(prefixed_path.AsStringW(), &find_file_data);
-
-  if (find_handle == INVALID_HANDLE_VALUE) {
-    return false;
-  }
-
-  // Adjust the path by removing the '*' used for the search.
-  int path_length = prefixed_path.length() - 1;
-  prefixed_path.Reset(path_length);
-
-  do {
-    if (!DeleteEntry(&find_file_data, &prefixed_path)) {
-      break;
-    }
-    prefixed_path.Reset(path_length);  // DeleteEntry adds to the path.
-  } while (FindNextFileW(find_handle, &find_file_data) != 0);
-
-  DWORD last_error = GetLastError();
-  // Always close handle.
-  FindClose(find_handle);
-  if (last_error != ERROR_NO_MORE_FILES) {
-    // Unexpected error, set and return.
-    SetLastError(last_error);
-    return false;
-  }
-  // All content deleted successfully, try to delete directory.
-  prefixed_path.Reset(path_length -
-                      1);  // Drop the "\" from the end of the path.
-  return RemoveDirectoryW(prefixed_path.AsStringW()) != 0;
-}
-
-static Directory::ExistsResult ExistsHelper(const wchar_t* dir_name) {
+Directory::ExistsResult Directory::Exists(const wchar_t* dir_name) {
   DWORD attributes = GetFileAttributesW(dir_name);
   if (attributes == INVALID_FILE_ATTRIBUTES) {
     DWORD last_error = GetLastError();
@@ -356,9 +379,8 @@ static Directory::ExistsResult ExistsHelper(const wchar_t* dir_name) {
 
 Directory::ExistsResult Directory::Exists(Namespace* namespc,
                                           const char* dir_name) {
-  const char* prefixed_dir_name = PrefixLongDirectoryPath(dir_name);
-  Utf8ToWideScope system_name(prefixed_dir_name);
-  return ExistsHelper(system_name.wide());
+  const auto path = ToWinAPIDirectoryPath(dir_name);
+  return Exists(path.get());
 }
 
 char* Directory::CurrentNoScope() {
@@ -378,12 +400,11 @@ char* Directory::CurrentNoScope() {
 }
 
 bool Directory::Create(Namespace* namespc, const char* dir_name) {
-  const char* prefixed_dir_name = PrefixLongDirectoryPath(dir_name);
-  Utf8ToWideScope system_name(prefixed_dir_name);
-  int create_status = CreateDirectoryW(system_name.wide(), nullptr);
+  const auto path = ToWinAPIDirectoryPath(dir_name);
+  int create_status = CreateDirectoryW(path.get(), nullptr);
   // If the directory already existed, treat it as a success.
   if ((create_status == 0) && (GetLastError() == ERROR_ALREADY_EXISTS) &&
-      (ExistsHelper(system_name.wide()) == EXISTS)) {
+      (Exists(path.get()) == EXISTS)) {
     return true;
   }
   return (create_status != 0);
@@ -399,8 +420,8 @@ const char* Directory::SystemTemp(Namespace* namespc) {
 // Creates a new temporary directory with a UUID as suffix.
 static const char* CreateTempFromUUID(const char* prefix) {
   PathBuffer path;
-  Utf8ToWideScope system_prefix(prefix);
-  if (!path.AddW(system_prefix.wide())) {
+  const auto system_prefix = Utf8ToWideChar(prefix);
+  if (!path.AddW(system_prefix.get())) {
     return nullptr;
   }
 
@@ -414,14 +435,14 @@ static const char* CreateTempFromUUID(const char* prefix) {
   if ((status != RPC_S_OK) && (status != RPC_S_UUID_LOCAL_ONLY)) {
     return nullptr;
   }
-  RPC_WSTR uuid_string;
+  wchar_t* uuid_string;
   status = UuidToStringW(&uuid, &uuid_string);
   if (status != RPC_S_OK) {
     return nullptr;
   }
 
   // RPC_WSTR is an unsigned short*, so we cast to wchar_t*.
-  if (!path.AddW(reinterpret_cast<wchar_t*>(uuid_string))) {
+  if (!path.AddW(uuid_string)) {
     return nullptr;
   }
   RpcStringFreeW(&uuid_string);
@@ -445,8 +466,8 @@ static const char* CreateTempFromUUID(const char* prefix) {
 // to have a small bound on the number of calls to CreateDirectoryW().
 const char* Directory::CreateTemp(Namespace* namespc, const char* prefix) {
   PathBuffer path;
-  Utf8ToWideScope system_prefix(prefix);
-  if (!path.AddW(system_prefix.wide())) {
+  const auto system_prefix = Utf8ToWideChar(prefix);
+  if (!path.AddW(system_prefix.get())) {
     return nullptr;
   }
 
@@ -485,39 +506,35 @@ const char* Directory::CreateTemp(Namespace* namespc, const char* prefix) {
 bool Directory::Delete(Namespace* namespc,
                        const char* dir_name,
                        bool recursive) {
-  const char* prefixed_dir_name = PrefixLongDirectoryPath(dir_name);
+  const auto path =
+      ToWinAPIDirectoryPath(dir_name, /*force_long_prefix=*/recursive);
   bool result = false;
-  Utf8ToWideScope system_dir_name(prefixed_dir_name);
   if (!recursive) {
-    if (File::GetType(namespc, prefixed_dir_name, true) == File::kIsDirectory) {
-      result = (RemoveDirectoryW(system_dir_name.wide()) != 0);
+    if (File::GetType(path.get(), /*follow_links=*/true) ==
+        File::kIsDirectory) {
+      result = (RemoveDirectoryW(path.get()) != 0);
     } else {
       SetLastError(ERROR_FILE_NOT_FOUND);
     }
   } else {
-    PathBuffer path;
-    if (path.AddW(system_dir_name.wide())) {
-      result = DeleteRecursively(&path);
-    }
+    RecursiveDeleter deleter;
+    result = deleter.DeleteRecursively(path);
   }
   return result;
 }
 
 bool Directory::Rename(Namespace* namespc,
-                       const char* path,
-                       const char* new_path) {
-  const char* prefixed_dir = PrefixLongDirectoryPath(path);
-  Utf8ToWideScope system_path(prefixed_dir);
-  ExistsResult exists = ExistsHelper(system_path.wide());
+                       const char* old_name,
+                       const char* new_name) {
+  const auto old_path = ToWinAPIDirectoryPath(old_name);
+  ExistsResult exists = Exists(old_path.get());
   if (exists != EXISTS) {
     SetLastError(ERROR_FILE_NOT_FOUND);
     return false;
   }
-  const char* prefixed_new_dir = PrefixLongDirectoryPath(new_path);
-  Utf8ToWideScope system_new_path(prefixed_new_dir);
+  const auto new_path = ToWinAPIDirectoryPath(new_name);
   DWORD flags = MOVEFILE_WRITE_THROUGH;
-  int move_status =
-      MoveFileExW(system_path.wide(), system_new_path.wide(), flags);
+  int move_status = MoveFileExW(old_path.get(), new_path.get(), flags);
   return (move_status != 0);
 }
 
diff --git a/runtime/bin/file.h b/runtime/bin/file.h
index 6c217a8ac5f..237d424fd9e 100644
--- a/runtime/bin/file.h
+++ b/runtime/bin/file.h
@@ -269,6 +269,9 @@ class File : public ReferenceCounted<File> {
   static bool IsAbsolutePath(const char* path);
   static const char* PathSeparator();
   static const char* StringEscapedPathSeparator();
+#if defined(DART_HOST_OS_WINDOWS)
+  static Type GetType(const wchar_t* path, bool follow_links);
+#endif
   static Type GetType(Namespace* namespc, const char* path, bool follow_links);
   static Identical AreIdentical(Namespace* namespc_1,
                                 const char* file_1,
diff --git a/runtime/bin/file_system_watcher_win.cc b/runtime/bin/file_system_watcher_win.cc
index 84a4c82a2ea..9ba9f687c54 100644
--- a/runtime/bin/file_system_watcher_win.cc
+++ b/runtime/bin/file_system_watcher_win.cc
@@ -36,9 +36,9 @@ intptr_t FileSystemWatcher::WatchPath(intptr_t id,
                                       int events,
                                       bool recursive) {
   USE(id);
-  Utf8ToWideScope name(path);
+  const auto name = Utf8ToWideChar(path);
   HANDLE dir =
-      CreateFileW(name.wide(), FILE_LIST_DIRECTORY,
+      CreateFileW(name.get(), FILE_LIST_DIRECTORY,
                   FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE,
                   nullptr, OPEN_EXISTING,
                   FILE_FLAG_BACKUP_SEMANTICS | FILE_FLAG_OVERLAPPED, nullptr);
diff --git a/runtime/bin/file_win.cc b/runtime/bin/file_win.cc
index a6c608bbbb8..d1132fd681b 100644
--- a/runtime/bin/file_win.cc
+++ b/runtime/bin/file_win.cc
@@ -7,7 +7,7 @@
 
 #include <functional>
 #include <memory>
-#include <string>
+#include <utility>
 
 #include <Shlwapi.h>  // NOLINT
 #include <fcntl.h>     // NOLINT
@@ -322,153 +322,126 @@ File* File::OpenFD(int fd) {
   return new File(new FileHandle(fd));
 }
 
-class StringRAII {
- public:
-  StringRAII(StringRAII& origin) {
-    own_ = origin.own_;
-    s_ = origin.release();
-  }
-
-  explicit StringRAII(const char* s) : own_(false), s_(s) {}
-  explicit StringRAII(char* s) : own_(true), s_(s) {}
-  ~StringRAII() {
-    if (own_) {
-      free(const_cast<char*>(s_));
+static std::unique_ptr<wchar_t[]> ConvertToAbsolutePath(
+    const std::unique_ptr<wchar_t[]>& path) {
+  // Initial buffer size is selected to avoid overallocating too much
+  // memory.
+  int buffer_size = 1024;
+  do {
+    auto buffer = std::make_unique<wchar_t[]>(buffer_size);
+    int full_path_length =
+        GetFullPathNameW(path.get(), buffer_size, buffer.get(),
+                         /*lpFilePart=*/nullptr);
+    if (full_path_length == 0) {
+      return nullptr;
     }
-  }
-  const char* str() const { return s_; }
-  const char* release() {
-    own_ = false;
-    return s_;
-  }
 
- private:
-  bool own_;
-  const char* s_;
-};
+    // Note: when sucessful full_path_length does *not* include terminating
+    // NUL character, but on failure it *does* include it when returning
+    // the size of buffer which we need. Hence comparison here is `<`, rather
+    // than `<=`.
+    if (full_path_length < buffer_size) {
+      return buffer;
+    }
 
-class Wchart {
- public:
-  explicit Wchart(int size) {
-    buf_ = reinterpret_cast<wchar_t*>(malloc(size * sizeof(wchar_t)));
-  }
-  ~Wchart() { free(buf_); }
-  wchar_t* buf() const { return buf_; }
-
- private:
-  wchar_t* buf_;
-};
-
-static StringRAII ConvertToAbsolutePath(const char* path,
-                                        bool* p_has_converted_successfully) {
-  const int kPathLength = 16384;
-  Wchart buffer(kPathLength);  // use some reasonably large initial buffer
-  Utf8ToWideScope path_utf8_to_wide(path);
-  *p_has_converted_successfully = true;
-  int full_path_length =
-      GetFullPathNameW(path_utf8_to_wide.wide(), kPathLength, buffer.buf(),
-                       /*lpFilePart=*/nullptr);
-  if (full_path_length == 0) {
-    *p_has_converted_successfully = false;
-    // GetFullPathNameW failed
-    return StringRAII(path);
-  }
-  if (full_path_length < kPathLength) {
-    WideToUtf8Scope scope(buffer.buf());
-    return StringRAII(Utils::StrDup(scope.utf8()));
-  }
-
-  // Try again with bigger buffer.
-  Wchart bigger_buffer(full_path_length);
-  if (GetFullPathNameW(path_utf8_to_wide.wide(), full_path_length,
-                       bigger_buffer.buf(),
-                       /*lpFilePart=*/nullptr) == 0) {
-    *p_has_converted_successfully = false;
-    // GetFullPathNameW failed
-    return StringRAII(path);
-  }
-  WideToUtf8Scope scope(bigger_buffer.buf());
-  return StringRAII(Utils::StrDup(scope.utf8()));
+    buffer_size = full_path_length;
+  } while (true);
 }
 
-static StringRAII PrefixLongPathIfExceedLimit(
-    const char* path,
-    bool is_file,
-    std::function<char*(int)> allocate) {
+static bool IsAbsolutePath(const wchar_t* pathname) {
+  if (pathname == nullptr) return false;
+  char first = pathname[0];
+  char second = pathname[1];
+  if (first == L'\\' && second == L'\\') return true;
+  if (second != L':') return false;
+  first |= 0x20;
+  char third = pathname[2];
+  return (first >= L'a') && (first <= L'z') &&
+         (third == L'\\' || third == L'/');
+}
+
+// Converts the given UTF8 path to wide char. If resulting path does not
+// fit into MAX_PATH / MAX_DIRECTORY_PATH (or if |force_long_prefix| is true)
+// then converts the path to the absolute `\\?\`-prefixed form.
+//
+// Note:
+// 1. Some WinAPI functions (like SetCurrentDirectoryW) are always limited
+//    to MAX_PATH long paths and converting to `\\?\`-prefixed form does not
+//    remove this limitation. Always check Win API documentation.
+// 2. This function might change relative path to an absolute path.
+static std::unique_ptr<wchar_t[]> ToWinAPIPath(const char* utf8_path,
+                                               bool is_file,
+                                               bool force_long_prefix) {
+  auto path = Utf8ToWideChar(utf8_path);
+
   // File name and Directory name have different size limit.
   // Reference: https://docs.microsoft.com/en-us/windows/win32/fileio/naming-a-file#maximum-path-length-limitation
   const int path_short_limit = is_file ? MAX_PATH : MAX_DIRECTORY_PATH;
 
-  const char* kLongPathPrefix = "\\\\?\\";
+  const wchar_t* kLongPathPrefix = L"\\\\?\\";
   const int kLongPathPrefixLength = 4;
 
-  // if absolute path is short or already prefixed, just return it.
-  if ((File::IsAbsolutePath(path) && strlen(path) < path_short_limit) ||
-      strncmp(path, kLongPathPrefix, kLongPathPrefixLength) == 0) {
-    return StringRAII(path);
+  std::unique_ptr<wchar_t[]> absolute_path;
+  if (!IsAbsolutePath(path.get())) {
+    absolute_path = ConvertToAbsolutePath(path);
+    if (absolute_path == nullptr) {
+      return path;
+    }
+  } else {
+    absolute_path = std::move(path);
   }
 
-  // Long relative path have to be converted to absolute path before prefixing.
-  bool is_ok = true;
-  StringRAII absolute_path_raii(
-      File::IsAbsolutePath(path)
-          ? StringRAII(path)
-          : StringRAII(ConvertToAbsolutePath(path, &is_ok)));
-  if (!is_ok) {
-    return StringRAII(path);
+  int path_length = wcslen(absolute_path.get());
+
+  if (!force_long_prefix && path_length < path_short_limit) {
+    if (path == nullptr) {
+      return absolute_path;
+    } else {
+      return path;
+    }
   }
-  const char* absolute_path = absolute_path_raii.str();
-  int length = strlen(absolute_path);
-  if (length < path_short_limit) {
-    // No need for a prefix if absolute path is short
-    return StringRAII(path);
-  }
-  if (strncmp(absolute_path, kLongPathPrefix, kLongPathPrefixLength) == 0) {
-    // Relative path converted to absolute could get a prefix.
-    return StringRAII(absolute_path);
+
+  if (wcsncmp(absolute_path.get(), kLongPathPrefix, kLongPathPrefixLength) ==
+      0) {
+    return absolute_path;
   }
 
   // Add prefix and replace forward slashes with backward slashes.
-  char* result = allocate((kLongPathPrefixLength + length + 1) * sizeof(char));
-  strncpy(result, kLongPathPrefix, kLongPathPrefixLength);
-  for (int i = 0; i < length; i++) {
-    result[kLongPathPrefixLength + i] =
-        absolute_path[i] == '/' ? '\\' : absolute_path[i];
+  auto result =
+      std::make_unique<wchar_t[]>(kLongPathPrefixLength + path_length + 1);
+  wcsncpy(result.get(), kLongPathPrefix, kLongPathPrefixLength);
+  for (int i = 0; i < path_length; i++) {
+    result.get()[kLongPathPrefixLength + i] =
+        absolute_path[i] == L'/' ? L'\\' : absolute_path[i];
   }
-  result[length + kLongPathPrefixLength] = '\0';
-  return StringRAII(result);
+  result.get()[path_length + kLongPathPrefixLength] = L'\0';
+  return result;
 }
 
-static const char* PrefixLongFilePath(const char* path) {
-  return PrefixLongPathIfExceedLimit(
-             path, /*is_file=*/true,
-             [](int size) {
-               return reinterpret_cast<char*>(Dart_ScopeAllocate(size));
-             })
-      .release();
+// Converts the given UTF8 path to wide char. If resulting path does not
+// fit into MAX_DIRECTORY_PATH (or if |force_long_prefix| is true) then
+// converts the path to the absolute `\\?\`-prefixed form.
+//
+// Note:
+// 1. Some WinAPI functions (like SetCurrentDirectoryW) are always limited
+//    to MAX_PATH long paths and converting to `\\?\`-prefixed form does not
+//    remove this limitation. Always check Win API documentation.
+// 2. This function might change relative path to an absolute path.
+static std::unique_ptr<wchar_t[]> ToWinAPIFilePath(
+    const char* path,
+    bool force_long_prefix = false) {
+  return ToWinAPIPath(path, /*is_file=*/true, force_long_prefix);
 }
 
-static StringRAII PrefixLongFilePathNoScope(const char* path) {
-  return PrefixLongPathIfExceedLimit(path, /*is_file=*/true, [](int size) {
-    return reinterpret_cast<char*>(malloc(size));
-  });
+std::unique_ptr<wchar_t[]> ToWinAPIDirectoryPath(
+    const char* path,
+    bool force_long_prefix /* = false */) {
+  return ToWinAPIPath(path, /*is_file=*/false, force_long_prefix);
 }
 
-const char* PrefixLongDirectoryPath(const char* path) {
-  return PrefixLongPathIfExceedLimit(
-             path, /*is_file=*/false,
-             [](int size) {
-               return reinterpret_cast<char*>(Dart_ScopeAllocate(size));
-             })
-      .release();
-}
-
-File* File::Open(Namespace* namespc, const char* path, FileOpenMode mode) {
-  // File::Open can be called without scope(when launching isolate),
-  // so it mallocs prefixed path
-  StringRAII string_raii = PrefixLongFilePathNoScope(path);
-  Utf8ToWideScope system_name(string_raii.str());
-  File* file = FileOpenW(system_name.wide(), mode);
+File* File::Open(Namespace* namespc, const char* name, FileOpenMode mode) {
+  const auto path = ToWinAPIFilePath(name);
+  File* file = FileOpenW(path.get(), mode);
   return file;
 }
 
@@ -479,13 +452,13 @@ Utils::CStringUniquePtr File::UriToPath(const char* uri) {
     return Utils::CreateCStringUniquePtr(nullptr);
   }
 
-  Utf8ToWideScope uri_w(uri_decoder.decoded());
-  if (!UrlIsFileUrlW(uri_w.wide())) {
+  const auto uri_w = Utf8ToWideChar(uri_decoder.decoded());
+  if (!UrlIsFileUrlW(uri_w.get())) {
     return Utils::CreateCStringUniquePtr(Utils::StrDup(uri_decoder.decoded()));
   }
   wchar_t filename_w[MAX_PATH];
   DWORD filename_len = MAX_PATH;
-  HRESULT result = PathCreateFromUrlW(uri_w.wide(), filename_w, &filename_len,
+  HRESULT result = PathCreateFromUrlW(uri_w.get(), filename_w, &filename_len,
                                       /* dwFlags= */ 0);
   if (result != S_OK) {
     return Utils::CreateCStringUniquePtr(nullptr);
@@ -519,7 +492,7 @@ File* File::OpenStdio(int fd) {
   return new File(new FileHandle(stdio_fd));
 }
 
-static bool StatHelper(wchar_t* path, struct __stat64* st) {
+static bool StatHelper(const wchar_t* path, struct __stat64* st) {
   int stat_status = _wstat64(path, st);
   if (stat_status != 0) {
     return false;
@@ -531,11 +504,14 @@ static bool StatHelper(wchar_t* path, struct __stat64* st) {
   return true;
 }
 
-bool File::Exists(Namespace* namespc, const char* name) {
-  StringRAII string_raii = PrefixLongFilePathNoScope(name);
-  Utf8ToWideScope system_name(string_raii.str());
+static bool FileExists(const wchar_t* path) {
   struct __stat64 st;
-  return StatHelper(system_name.wide(), &st);
+  return StatHelper(path, &st);
+}
+
+bool File::Exists(Namespace* namespc, const char* name) {
+  const auto path = ToWinAPIFilePath(name);
+  return FileExists(path.get());
 }
 
 bool File::ExistsUri(Namespace* namespc, const char* uri) {
@@ -548,12 +524,12 @@ bool File::ExistsUri(Namespace* namespc, const char* uri) {
 }
 
 bool File::Create(Namespace* namespc, const char* name, bool exclusive) {
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
+  const auto path = ToWinAPIFilePath(name);
   int flags = O_RDONLY | O_CREAT;
   if (exclusive) {
     flags |= O_EXCL;
   }
-  int fd = _wopen(system_name.wide(), flags, 0666);
+  int fd = _wopen(path.get(), flags, 0666);
   if (fd < 0) {
     return false;
   }
@@ -593,13 +569,14 @@ typedef struct _REPARSE_DATA_BUFFER {
 bool File::CreateLink(Namespace* namespc,
                       const char* utf8_name,
                       const char* utf8_target) {
-  Utf8ToWideScope name(PrefixLongFilePath(utf8_name));
-  Utf8ToWideScope target(PrefixLongFilePath(utf8_target));
-  DWORD flags = SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE;
+  const auto name = ToWinAPIFilePath(utf8_name);
 
-  File::Type type;
+  std::unique_ptr<wchar_t[]> target;
+  bool target_is_directory;
   if (File::IsAbsolutePath(utf8_target)) {
-    type = File::GetType(namespc, utf8_target, true);
+    target = ToWinAPIFilePath(utf8_target);
+    target_is_directory =
+        File::GetType(target.get(), /*follow_links=*/true) == kIsDirectory;
   } else {
     // The path of `target` is relative to `name`.
     //
@@ -618,15 +595,17 @@ bool File::CreateLink(Namespace* namespc,
     // 1. target_path := name                           ..\..\Link
     // 2. target_path := remove_file(target_path)       ..\..\
     // 3. target_path := combine(target_path, target)   ..\..\..\Dir\MyFile
+    target = Utf8ToWideChar(utf8_target);
 
     // 1. target_path := name
-    intptr_t target_path_max_length = name.length() + target.length();
-    Wchart target_path(target_path_max_length);
-    wcscpy_s(target_path.buf(), target_path_max_length, name.wide());
+    intptr_t target_path_max_length =
+        wcslen(name.get()) + wcslen(target.get()) + 2;
+    auto target_path = std::make_unique<wchar_t[]>(target_path_max_length);
+    wcscpy_s(target_path.get(), target_path_max_length, name.get());
 
     // 2. target_path := remove_file(target_path)
     HRESULT remove_result =
-        PathCchRemoveFileSpec(target_path.buf(), target_path_max_length);
+        PathCchRemoveFileSpec(target_path.get(), target_path_max_length);
     if (remove_result == S_FALSE) {
       // If the file component could not be removed, then `name` is
       // top-level, like "C:\" or "/". Attempts to create files at those paths
@@ -640,27 +619,29 @@ bool File::CreateLink(Namespace* namespc,
 
     // 3. target_path := combine(target_path, target)
     HRESULT combine_result = PathCchCombineEx(
-        target_path.buf(), target_path_max_length, target_path.buf(),
-        target.wide(), PATHCCH_ALLOW_LONG_PATHS);
+        target_path.get(), target_path_max_length, target_path.get(),
+        target.get(), PATHCCH_ALLOW_LONG_PATHS);
     if (combine_result != S_OK) {
       SetLastError(combine_result);
       return false;
     }
 
-    type = PathIsDirectoryW(target_path.buf()) ? kIsDirectory : kIsFile;
+    target_is_directory =
+        File::GetType(target_path.get(), /*follow_links=*/true) == kIsDirectory;
   }
 
-  if (type == kIsDirectory) {
+  DWORD flags = SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE;
+  if (target_is_directory) {
     flags |= SYMBOLIC_LINK_FLAG_DIRECTORY;
   }
-  int create_status = CreateSymbolicLinkW(name.wide(), target.wide(), flags);
+  int create_status = CreateSymbolicLinkW(name.get(), target.get(), flags);
 
   // If running on a Windows 10 build older than 14972, an invalid parameter
   // error will be returned when trying to use the
   // SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE flag. Retry without the flag.
   if ((create_status == 0) && (GetLastError() == ERROR_INVALID_PARAMETER)) {
     flags &= ~SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE;
-    create_status = CreateSymbolicLinkW(name.wide(), target.wide(), flags);
+    create_status = CreateSymbolicLinkW(name.get(), target.get(), flags);
   }
 
   return (create_status != 0);
@@ -678,15 +659,14 @@ bool File::CreatePipe(Namespace* namespc, File** readPipe, File** writePipe) {
 }
 
 bool File::Delete(Namespace* namespc, const char* name) {
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
-  int status = _wremove(system_name.wide());
+  const auto path = ToWinAPIFilePath(name);
+  int status = _wremove(path.get());
   return status != -1;
 }
 
-bool File::DeleteLink(Namespace* namespc, const char* name) {
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
+static bool DeleteLinkHelper(const wchar_t* path) {
   bool result = false;
-  DWORD attributes = GetFileAttributesW(system_name.wide());
+  DWORD attributes = GetFileAttributesW(path);
   if ((attributes == INVALID_FILE_ATTRIBUTES) ||
       ((attributes & FILE_ATTRIBUTE_REPARSE_POINT) == 0)) {
     SetLastError(ERROR_NOT_A_REPARSE_POINT);
@@ -695,207 +675,176 @@ bool File::DeleteLink(Namespace* namespc, const char* name) {
   if ((attributes & FILE_ATTRIBUTE_DIRECTORY) != 0) {
     // It's a junction, which is a special type of directory, or a symbolic
     // link to a directory. Remove the directory.
-    result = (RemoveDirectoryW(system_name.wide()) != 0);
+    result = (RemoveDirectoryW(path) != 0);
   } else {
     // Symbolic link to a file. Remove the file.
-    result = (DeleteFileW(system_name.wide()) != 0);
+    result = (DeleteFileW(path) != 0);
   }
   return result;
 }
 
-bool File::Rename(Namespace* namespc,
-                  const char* old_path,
-                  const char* new_path) {
-  const char* prefixed_old_path = PrefixLongFilePath(old_path);
-  File::Type type = GetType(namespc, prefixed_old_path, false);
-  if (type != kIsFile) {
+bool File::DeleteLink(Namespace* namespc, const char* name) {
+  const auto path = ToWinAPIFilePath(name);
+  return DeleteLinkHelper(path.get());
+}
+
+static bool RenameHelper(File::Type expected,
+                         const char* old_name,
+                         const char* new_name) {
+  const auto old_path = ToWinAPIFilePath(old_name);
+  File::Type type = File::GetType(old_path.get(), /*follow_links=*/false);
+  if (type != expected) {
     SetLastError(ERROR_FILE_NOT_FOUND);
     return false;
   }
-  const char* prefixed_new_path = PrefixLongFilePath(new_path);
-  Utf8ToWideScope system_old_path(prefixed_old_path);
-  Utf8ToWideScope system_new_path(prefixed_new_path);
+  const auto new_path = ToWinAPIFilePath(new_name);
   DWORD flags = MOVEFILE_WRITE_THROUGH | MOVEFILE_REPLACE_EXISTING;
 
   // Symbolic links (e.g. produced by Link.create) to directories on Windows
   // appear as special directories. MoveFileExW's MOVEFILE_REPLACE_EXISTING
   // does not allow for replacement of directories, so we need to remove it
   // before renaming.
-  if ((Directory::Exists(namespc, prefixed_new_path) == Directory::EXISTS) &&
-      (GetType(namespc, prefixed_new_path, false) == kIsLink)) {
+  if ((Directory::Exists(new_path.get()) == Directory::EXISTS) &&
+      (File::GetType(new_path.get(), /*follow_links=*/false) ==
+       File::kIsLink)) {
     // Bail out if the DeleteLink call fails.
-    if (!DeleteLink(namespc, prefixed_new_path)) {
+    if (!DeleteLinkHelper(new_path.get())) {
       return false;
     }
   }
-  int move_status =
-      MoveFileExW(system_old_path.wide(), system_new_path.wide(), flags);
+  int move_status = MoveFileExW(old_path.get(), new_path.get(), flags);
   return (move_status != 0);
 }
 
+bool File::Rename(Namespace* namespc,
+                  const char* old_name,
+                  const char* new_name) {
+  return RenameHelper(File::kIsFile, old_name, new_name);
+}
+
 bool File::RenameLink(Namespace* namespc,
-                      const char* old_path,
-                      const char* new_path) {
-  const char* prefixed_old_path = PrefixLongFilePath(old_path);
-  File::Type type = GetType(namespc, prefixed_old_path, false);
-  if (type != kIsLink) {
-    SetLastError(ERROR_FILE_NOT_FOUND);
-    return false;
-  }
-  Utf8ToWideScope system_old_path(prefixed_old_path);
-  const char* prefixed_new_path = PrefixLongFilePath(new_path);
-  Utf8ToWideScope system_new_path(prefixed_new_path);
-  DWORD flags = MOVEFILE_WRITE_THROUGH | MOVEFILE_REPLACE_EXISTING;
-
-  // Symbolic links (e.g. produced by Link.create) to directories on Windows
-  // appear as special directories. MoveFileExW's MOVEFILE_REPLACE_EXISTING
-  // does not allow for replacement of directories, so we need to remove it
-  // before renaming.
-  if ((Directory::Exists(namespc, prefixed_new_path) == Directory::EXISTS) &&
-      (GetType(namespc, prefixed_new_path, false) == kIsLink)) {
-    // Bail out if the DeleteLink call fails.
-    if (!DeleteLink(namespc, prefixed_new_path)) {
-      return false;
-    }
-  }
-  int move_status =
-      MoveFileExW(system_old_path.wide(), system_new_path.wide(), flags);
-  return (move_status != 0);
+                      const char* old_name,
+                      const char* new_name) {
+  return RenameHelper(File::kIsLink, old_name, new_name);
 }
 
-static wchar_t* CopyToDartScopeString(wchar_t* string) {
-  wchar_t* wide_path = reinterpret_cast<wchar_t*>(
-      Dart_ScopeAllocate(MAX_PATH * sizeof(wchar_t) + 1));
-  wcscpy(wide_path, string);
-  return wide_path;
-}
-
-static wchar_t* CopyIntoTempFile(const char* src, const char* dest) {
-  // This function will copy the file to a temp file in the destination
-  // directory and return the path of temp file.
-  // Creating temp file name has the same logic as Directory::CreateTemp(),
-  // which tries with the rng and falls back to a uuid if it failed.
-  const char* last_back_slash = strrchr(dest, '\\');
-  // It is possible the path uses forwardslash as path separator.
-  const char* last_forward_slash = strrchr(dest, '/');
-  const char* last_path_separator = nullptr;
-  if (last_back_slash == nullptr && last_forward_slash == nullptr) {
-    return nullptr;
-  } else if (last_forward_slash != nullptr && last_forward_slash != nullptr) {
-    // If both types occur in the path, use the one closer to the end.
-    if (last_back_slash - dest > last_forward_slash - dest) {
-      last_path_separator = last_back_slash;
-    } else {
-      last_path_separator = last_forward_slash;
+static std::unique_ptr<wchar_t[]> GetDirectoryPath(
+    const std::unique_ptr<wchar_t[]>& path) {
+  for (intptr_t i = wcslen(path.get()) - 1; i >= 0; --i) {
+    if (path.get()[i] == '\\' || path.get()[i] == '/') {
+      auto result = std::make_unique<wchar_t[]>(i + 1);
+      wcsncpy(result.get(), path.get(), i);
+      return result;
     }
-  } else {
-    last_path_separator =
-        (last_forward_slash == nullptr) ? last_back_slash : last_forward_slash;
-  }
-  int length_of_parent_dir = last_path_separator - dest + 1;
-  if (length_of_parent_dir + 8 > MAX_PATH) {
-    return nullptr;
-  }
-  uint32_t suffix_bytes = 0;
-  const int kSuffixSize = sizeof(suffix_bytes);
-  if (Crypto::GetRandomBytes(kSuffixSize,
-                             reinterpret_cast<uint8_t*>(&suffix_bytes))) {
-    PathBuffer buffer;
-    char* dir = reinterpret_cast<char*>(
-        Dart_ScopeAllocate(1 + sizeof(char) * length_of_parent_dir));
-    memmove(dir, dest, length_of_parent_dir);
-    dir[length_of_parent_dir] = '\0';
-    if (!buffer.Add(dir)) {
-      return nullptr;
-    }
-
-    char suffix[8 + 1];
-    Utils::SNPrint(suffix, sizeof(suffix), "%x", suffix_bytes);
-    Utf8ToWideScope source_path(src);
-    if (!buffer.Add(suffix)) {
-      return nullptr;
-    }
-    if (CopyFileExW(source_path.wide(), buffer.AsStringW(), nullptr, nullptr,
-                    nullptr, 0) != 0) {
-      return CopyToDartScopeString(buffer.AsStringW());
-    }
-    // If CopyFileExW() fails to copy to a temp file with random hex, fall
-    // back to copy to a uuid temp file.
-  }
-  // UUID has a total of 36 characters in the form of
-  // xxxxxxxx-xxxx-Mxxx-Nxxx-xxxxxxxxxxxx.
-  if (length_of_parent_dir + 36 > MAX_PATH) {
-    return nullptr;
-  }
-  UUID uuid;
-  RPC_STATUS status = UuidCreateSequential(&uuid);
-  if ((status != RPC_S_OK) && (status != RPC_S_UUID_LOCAL_ONLY)) {
-    return nullptr;
-  }
-  RPC_WSTR uuid_string;
-  status = UuidToStringW(&uuid, &uuid_string);
-  if (status != RPC_S_OK) {
-    return nullptr;
-  }
-  PathBuffer buffer;
-  char* dir = reinterpret_cast<char*>(
-      Dart_ScopeAllocate(1 + sizeof(char) * length_of_parent_dir));
-  memmove(dir, dest, length_of_parent_dir);
-  dir[length_of_parent_dir] = '\0';
-  Utf8ToWideScope dest_path(dir);
-  if (!buffer.AddW(dest_path.wide()) ||
-      !buffer.AddW(reinterpret_cast<wchar_t*>(uuid_string))) {
-    return nullptr;
-  }
-
-  RpcStringFreeW(&uuid_string);
-  Utf8ToWideScope source_path(src);
-  if (CopyFileExW(source_path.wide(), buffer.AsStringW(), nullptr, nullptr,
-                  nullptr, 0) != 0) {
-    return CopyToDartScopeString(buffer.AsStringW());
   }
   return nullptr;
 }
 
+static void FreeUUID(wchar_t* ptr) {
+  RpcStringFreeW(&ptr);
+}
+
+static std::unique_ptr<wchar_t, decltype(FreeUUID) *> GenerateUUIDString() {
+  UUID uuid;
+  RPC_STATUS status = UuidCreateSequential(&uuid);
+  if ((status != RPC_S_OK) && (status != RPC_S_UUID_LOCAL_ONLY)) {
+    return {nullptr, nullptr};
+  }
+  wchar_t* uuid_string;
+  status = UuidToStringW(&uuid, &uuid_string);
+  if (status != RPC_S_OK) {
+    return {nullptr, nullptr};
+  }
+
+  return {uuid_string, &FreeUUID};
+}
+
+// This function will copy the |src| file to a temporary file in the
+// directory where |dest| resides and returns the path of temp file.
+static std::unique_ptr<wchar_t[]> CopyIntoTempFile(
+    const std::unique_ptr<wchar_t[]>& src,
+    const std::unique_ptr<wchar_t[]>& dest) {
+  const auto dir = GetDirectoryPath(dest);
+  if (dir == nullptr) {
+    return nullptr;
+  }
+
+  uint32_t suffix_bytes = 0;
+  const int kSuffixSize = sizeof(suffix_bytes);
+  if (Crypto::GetRandomBytes(kSuffixSize,
+                             reinterpret_cast<uint8_t*>(&suffix_bytes))) {
+    const size_t file_path_buf_size = wcslen(dir.get()) + 8 + 1;
+    auto file_path = std::make_unique<wchar_t[]>(file_path_buf_size);
+    swprintf(file_path.get(), file_path_buf_size, L"%s%x", dir.get(),
+             suffix_bytes);
+
+    if (CopyFileExW(src.get(), file_path.get(), nullptr, nullptr, nullptr, 0) !=
+        0) {
+      return file_path;
+    }
+
+    // If CopyFileExW() fails to copy to a temp file with random hex, fall
+    // back to copy to a uuid temp file.
+  }
+
+  const auto uuid_str = GenerateUUIDString();
+  if (uuid_str == nullptr) {
+    return nullptr;
+  }
+
+  const size_t file_path_buf_size =
+      wcslen(dir.get()) + wcslen(uuid_str.get()) + 1;
+  auto file_path = std::make_unique<wchar_t[]>(file_path_buf_size);
+  swprintf(file_path.get(), file_path_buf_size, L"%s%s", dir.get(),
+           uuid_str.get());
+
+  if (CopyFileExW(src.get(), file_path.get(), nullptr, nullptr, nullptr, 0) !=
+      0) {
+    return file_path;
+  }
+
+  return nullptr;
+}
+
 bool File::Copy(Namespace* namespc,
-                const char* old_path,
-                const char* new_path) {
-  const char* prefixed_old_path = PrefixLongFilePath(old_path);
-  const char* prefixed_new_path = PrefixLongFilePath(new_path);
-  File::Type type = GetType(namespc, prefixed_old_path, false);
+                const char* old_name,
+                const char* new_name) {
+  // We are going to concatenate old path with temporary file names in
+  // CopyIntoTempFile so we force long prefix no matter what.
+  const auto old_path = ToWinAPIFilePath(old_name, /*force_long_prefix=*/true);
+  const auto new_path = ToWinAPIFilePath(new_name);
+  File::Type type = GetType(old_path.get(), /*follow_links=*/false);
   if (type != kIsFile) {
     SetLastError(ERROR_FILE_NOT_FOUND);
     return false;
   }
 
-  wchar_t* temp_file = CopyIntoTempFile(prefixed_old_path, prefixed_new_path);
+  const auto temp_file = CopyIntoTempFile(old_path, new_path);
   if (temp_file == nullptr) {
     // If temp file creation fails, fall back on doing a direct copy.
-    Utf8ToWideScope system_old_path(prefixed_old_path);
-    Utf8ToWideScope system_new_path(prefixed_new_path);
-    return CopyFileExW(system_old_path.wide(), system_new_path.wide(), nullptr,
-                       nullptr, nullptr, 0) != 0;
+    return CopyFileExW(old_path.get(), new_path.get(), nullptr, nullptr,
+                       nullptr, 0) != 0;
   }
-  Utf8ToWideScope system_new_dest(prefixed_new_path);
 
   // Remove the existing file. Otherwise, renaming will fail.
-  if (Exists(namespc, prefixed_new_path)) {
-    DeleteFileW(system_new_dest.wide());
+  if (FileExists(new_path.get())) {
+    DeleteFileW(new_path.get());
   }
 
-  if (!MoveFileW(temp_file, system_new_dest.wide())) {
+  if (!MoveFileW(temp_file.get(), new_path.get())) {
     DWORD error = GetLastError();
-    DeleteFileW(temp_file);
+    DeleteFileW(temp_file.get());
     SetLastError(error);
     return false;
   }
+
   return true;
 }
 
 int64_t File::LengthFromPath(Namespace* namespc, const char* name) {
   struct __stat64 st;
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
-  if (!StatHelper(system_name.wide(), &st)) {
+  const auto path = ToWinAPIFilePath(name);
+  if (!StatHelper(path.get(), &st)) {
     return -1;
   }
   return st.st_size;
@@ -905,10 +854,9 @@ const char* File::LinkTarget(Namespace* namespc,
                              const char* pathname,
                              char* dest,
                              int dest_size) {
-  const wchar_t* name =
-      StringUtilsWin::Utf8ToWide(PrefixLongFilePath(pathname));
+  const auto path = ToWinAPIFilePath(pathname);
   HANDLE dir_handle = CreateFileW(
-      name, GENERIC_READ,
+      path.get(), GENERIC_READ,
       FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE, nullptr,
       OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS | FILE_FLAG_OPEN_REPARSE_POINT,
       nullptr);
@@ -993,13 +941,12 @@ const char* File::LinkTarget(Namespace* namespc,
 }
 
 void File::Stat(Namespace* namespc, const char* name, int64_t* data) {
-  const char* prefixed_name = PrefixLongFilePath(name);
-  File::Type type = GetType(namespc, prefixed_name, true);
+  const auto path = ToWinAPIFilePath(name);
+  File::Type type = GetType(path.get(), /*follow_links=*/true);
   data[kType] = type;
   if (type != kDoesNotExist) {
     struct _stat64 st;
-    Utf8ToWideScope system_name(prefixed_name);
-    int stat_status = _wstat64(system_name.wide(), &st);
+    int stat_status = _wstat64(path.get(), &st);
     if (stat_status == 0) {
       data[kCreatedTime] = st.st_ctime * 1000;
       data[kModifiedTime] = st.st_mtime * 1000;
@@ -1014,8 +961,8 @@ void File::Stat(Namespace* namespc, const char* name, int64_t* data) {
 
 time_t File::LastAccessed(Namespace* namespc, const char* name) {
   struct __stat64 st;
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
-  if (!StatHelper(system_name.wide(), &st)) {
+  const auto path = ToWinAPIFilePath(name);
+  if (!StatHelper(path.get(), &st)) {
     return -1;
   }
   return st.st_atime;
@@ -1023,8 +970,8 @@ time_t File::LastAccessed(Namespace* namespc, const char* name) {
 
 time_t File::LastModified(Namespace* namespc, const char* name) {
   struct __stat64 st;
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
-  if (!StatHelper(system_name.wide(), &st)) {
+  const auto path = ToWinAPIFilePath(name);
+  if (!StatHelper(path.get(), &st)) {
     return -1;
   }
   return st.st_mtime;
@@ -1034,8 +981,8 @@ bool File::SetLastAccessed(Namespace* namespc,
                            const char* name,
                            int64_t millis) {
   struct __stat64 st;
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
-  if (!StatHelper(system_name.wide(), &st)) {  // Checks that it is a file.
+  const auto path = ToWinAPIFilePath(name);
+  if (!StatHelper(path.get(), &st)) {  // Checks that it is a file.
     return false;
   }
 
@@ -1047,7 +994,7 @@ bool File::SetLastAccessed(Namespace* namespc,
   // So set the file access time directly using SetFileTime.
   FILETIME at = GetFiletimeFromMillis(millis);
   HANDLE file_handle =
-      CreateFileW(system_name.wide(), FILE_WRITE_ATTRIBUTES,
+      CreateFileW(path.get(), FILE_WRITE_ATTRIBUTES,
                   FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE,
                   nullptr, OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS, nullptr);
   if (file_handle == INVALID_HANDLE_VALUE) {
@@ -1063,8 +1010,8 @@ bool File::SetLastModified(Namespace* namespc,
                            int64_t millis) {
   // First get the current times.
   struct __stat64 st;
-  Utf8ToWideScope system_name(PrefixLongFilePath(name));
-  if (!StatHelper(system_name.wide(), &st)) {
+  const auto path = ToWinAPIFilePath(name);
+  if (!StatHelper(path.get(), &st)) {
     return false;
   }
 
@@ -1072,7 +1019,7 @@ bool File::SetLastModified(Namespace* namespc,
   struct __utimbuf64 times;
   times.actime = st.st_atime;
   times.modtime = millis / kMillisecondsPerSecond;
-  return _wutime64(system_name.wide(), &times) == 0;
+  return _wutime64(path.get(), &times) == 0;
 }
 
 // Keep this function synchronized with the behavior
@@ -1092,10 +1039,10 @@ const char* File::GetCanonicalPath(Namespace* namespc,
                                    const char* pathname,
                                    char* dest,
                                    int dest_size) {
-  Utf8ToWideScope system_name(PrefixLongFilePath(pathname));
+  const auto path = ToWinAPIFilePath(pathname);
   HANDLE file_handle =
-      CreateFileW(system_name.wide(), 0, FILE_SHARE_READ, nullptr,
-                  OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS, nullptr);
+      CreateFileW(path.get(), 0, FILE_SHARE_READ, nullptr, OPEN_EXISTING,
+                  FILE_FLAG_BACKUP_SEMANTICS, nullptr);
   if (file_handle == INVALID_HANDLE_VALUE) {
     return nullptr;
   }
@@ -1108,8 +1055,9 @@ const char* File::GetCanonicalPath(Namespace* namespc,
     SetLastError(error);
     return nullptr;
   }
-  auto path = std::unique_ptr<wchar_t[]>(new wchar_t[required_size]);
-  int result_size = GetFinalPathNameByHandle(file_handle, path.get(),
+
+  const auto canonical_path = std::make_unique<wchar_t[]>(required_size);
+  int result_size = GetFinalPathNameByHandle(file_handle, canonical_path.get(),
                                              required_size, VOLUME_NAME_DOS);
   ASSERT(result_size <= required_size - 1);
   CloseHandle(file_handle);
@@ -1117,16 +1065,18 @@ const char* File::GetCanonicalPath(Namespace* namespc,
   // Remove leading \\?\ since it is only to overcome MAX_PATH limitation.
   // Leave it if input used it though.
   int offset = 0;
-  if ((result_size > 4) && (wcsncmp(path.get(), L"\\\\?\\", 4) == 0) &&
+  if ((result_size > 4) &&
+      (wcsncmp(canonical_path.get(), L"\\\\?\\", 4) == 0) &&
       (strncmp(pathname, "\\\\?\\", 4) != 0)) {
-    if ((result_size > 8) && (wcsncmp(path.get(), L"\\\\?\\UNC\\", 8) == 0)) {
+    if ((result_size > 8) &&
+        (wcsncmp(canonical_path.get(), L"\\\\?\\UNC\\", 8) == 0)) {
       // Leave '\\?\UNC\' prefix intact - stripping it makes invalid UNC name.
     } else {
       offset = 4;
     }
   }
-  int utf8_size = WideCharToMultiByte(CP_UTF8, 0, path.get() + offset, -1,
-                                      nullptr, 0, nullptr, nullptr);
+  int utf8_size = WideCharToMultiByte(CP_UTF8, 0, canonical_path.get() + offset,
+                                      -1, nullptr, 0, nullptr, nullptr);
   if (dest == nullptr) {
     dest = DartUtils::ScopedCString(utf8_size);
     dest_size = utf8_size;
@@ -1134,8 +1084,8 @@ const char* File::GetCanonicalPath(Namespace* namespc,
   if (dest_size != 0) {
     ASSERT(utf8_size <= dest_size);
   }
-  if (0 == WideCharToMultiByte(CP_UTF8, 0, path.get() + offset, -1, dest,
-                               dest_size, nullptr, nullptr)) {
+  if (0 == WideCharToMultiByte(CP_UTF8, 0, canonical_path.get() + offset, -1,
+                               dest, dest_size, nullptr, nullptr)) {
     return nullptr;
   }
   return dest;
@@ -1157,27 +1107,17 @@ File::StdioHandleType File::GetStdioHandleType(int fd) {
   return kPipe;
 }
 
-File::Type File::GetType(Namespace* namespc,
-                         const char* pathname,
-                         bool follow_links) {
-  // File::GetType can be called without scope(when launching isolate),
-  // so it mallocs prefixed path.
-  StringRAII string_raii = PrefixLongFilePathNoScope(pathname);
-  const char* prefixed_path = string_raii.str();
-
-  // Convert to wchar_t string.
-  Utf8ToWideScope name(prefixed_path);
-  DWORD attributes = GetFileAttributesW(name.wide());
+File::Type File::GetType(const wchar_t* path, bool follow_links) {
+  DWORD attributes = GetFileAttributesW(path);
   if (attributes == INVALID_FILE_ATTRIBUTES) {
-    return kDoesNotExist;
+    return File::kDoesNotExist;
   } else if ((attributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0) {
     if (follow_links) {
       HANDLE target_handle = CreateFileW(
-          name.wide(), 0,
-          FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE, nullptr,
-          OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS, nullptr);
+          path, 0, FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE,
+          nullptr, OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS, nullptr);
       if (target_handle == INVALID_HANDLE_VALUE) {
-        return kDoesNotExist;
+        return File::kDoesNotExist;
       } else {
         BY_HANDLE_FILE_INFORMATION info;
         if (!GetFileInformationByHandle(target_handle, &info)) {
@@ -1186,16 +1126,23 @@ File::Type File::GetType(Namespace* namespc,
         }
         CloseHandle(target_handle);
         return ((info.dwFileAttributes & FILE_ATTRIBUTE_DIRECTORY) != 0)
-                   ? kIsDirectory
-                   : kIsFile;
+                   ? File::kIsDirectory
+                   : File::kIsFile;
       }
     } else {
-      return kIsLink;
+      return File::kIsLink;
     }
   } else if ((attributes & FILE_ATTRIBUTE_DIRECTORY) != 0) {
-    return kIsDirectory;
+    return File::kIsDirectory;
   }
-  return kIsFile;
+  return File::kIsFile;
+}
+
+File::Type File::GetType(Namespace* namespc,
+                         const char* name,
+                         bool follow_links) {
+  const auto path = ToWinAPIFilePath(name);
+  return GetType(path.get(), follow_links);
 }
 
 File::Identical File::AreIdentical(Namespace* namespc_1,
@@ -1205,12 +1152,11 @@ File::Identical File::AreIdentical(Namespace* namespc_1,
   USE(namespc_1);
   USE(namespc_2);
   BY_HANDLE_FILE_INFORMATION file_info[2];
-  const char* file_names[2] = {PrefixLongFilePath(file_1),
-                               PrefixLongFilePath(file_2)};
+  const std::unique_ptr<wchar_t[]> file_names[2] = {ToWinAPIFilePath(file_1),
+                                                    ToWinAPIFilePath(file_2)};
   for (int i = 0; i < 2; ++i) {
-    Utf8ToWideScope wide_name(file_names[i]);
     HANDLE file_handle = CreateFileW(
-        wide_name.wide(), 0,
+        file_names[i].get(), 0,
         FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE, nullptr,
         OPEN_EXISTING,
         FILE_FLAG_BACKUP_SEMANTICS | FILE_FLAG_OPEN_REPARSE_POINT, nullptr);
diff --git a/runtime/bin/file_win.h b/runtime/bin/file_win.h
index ef5f73255ce..9ba7da02b71 100644
--- a/runtime/bin/file_win.h
+++ b/runtime/bin/file_win.h
@@ -5,6 +5,8 @@
 #ifndef RUNTIME_BIN_FILE_WIN_H_
 #define RUNTIME_BIN_FILE_WIN_H_
 
+#include <memory>
+
 #include "bin/file.h"
 
 // The limit for a regular directory is 248.
@@ -14,7 +16,18 @@
 namespace dart {
 namespace bin {
 
-const char* PrefixLongDirectoryPath(const char* path);
+// Converts the given UTF8 path to wide char. If resulting path does not
+// fit into MAX_DIRECTORY_PATH (or if |force_long_prefix| is true) then
+// converts the path to the absolute `\\?\`-prefixed form.
+//
+// Note:
+// 1. Some WinAPI functions (like SetCurrentDirectoryW) are always limited
+//    to MAX_PATH long paths and converting to `\\?\`-prefixed form does not
+//    remove this limitation. Always check Win API documentation.
+// 2. This function might change relative path to an absolute path.
+std::unique_ptr<wchar_t[]> ToWinAPIDirectoryPath(
+    const char* path,
+    bool force_long_prefix = false);
 
 }  // namespace bin
 }  // namespace dart
diff --git a/runtime/bin/namespace_win.cc b/runtime/bin/namespace_win.cc
index 141ca38c9ee..297c44ca4fc 100644
--- a/runtime/bin/namespace_win.cc
+++ b/runtime/bin/namespace_win.cc
@@ -48,11 +48,14 @@ const char* Namespace::GetCurrent(Namespace* namespc) {
 }
 
 bool Namespace::SetCurrent(Namespace* namespc, const char* path) {
-  // TODO(zichangguo): "\\?\" prepended long path doesn't work.
-  // https://github.com/dart-lang/sdk/issues/42416
-  path = PrefixLongDirectoryPath(path);
-  Utf8ToWideScope system_path(path);
-  bool result = SetCurrentDirectoryW(system_path.wide()) != 0;
+  // 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
+  const auto system_path = Utf8ToWideChar(path);
+  bool result = SetCurrentDirectoryW(system_path.get()) != 0;
   return result;
 }
 
diff --git a/runtime/bin/socket_base_win.cc b/runtime/bin/socket_base_win.cc
index 852395395e3..a46a2c024e3 100644
--- a/runtime/bin/socket_base_win.cc
+++ b/runtime/bin/socket_base_win.cc
@@ -307,12 +307,12 @@ bool SocketBase::ReverseLookup(const RawAddr& addr,
 
 bool SocketBase::ParseAddress(int type, const char* address, RawAddr* addr) {
   int result;
-  Utf8ToWideScope system_address(address);
+  const auto system_address = Utf8ToWideChar(address);
   if (type == SocketAddress::TYPE_IPV4) {
-    result = InetPton(AF_INET, system_address.wide(), &addr->in.sin_addr);
+    result = InetPton(AF_INET, system_address.get(), &addr->in.sin_addr);
   } else {
     ASSERT(type == SocketAddress::TYPE_IPV6);
-    result = InetPton(AF_INET6, system_address.wide(), &addr->in6.sin6_addr);
+    result = InetPton(AF_INET6, system_address.get(), &addr->in6.sin6_addr);
   }
   return result == 1;
 }
diff --git a/runtime/bin/utils_win.cc b/runtime/bin/utils_win.cc
index b05e4f28766..79a7eb80129 100644
--- a/runtime/bin/utils_win.cc
+++ b/runtime/bin/utils_win.cc
@@ -7,6 +7,7 @@
 
 #include <errno.h>  // NOLINT
 #include <time.h>   // NOLINT
+#include <memory>
 
 #include "bin/utils.h"
 #include "bin/utils_win.h"
@@ -237,6 +238,13 @@ void TimerUtils::Sleep(int64_t millis) {
   ::Sleep(millis);
 }
 
+std::unique_ptr<wchar_t[]> Utf8ToWideChar(const char* path) {
+  int wide_len = MultiByteToWideChar(CP_UTF8, 0, path, -1, nullptr, 0);
+  auto result = std::make_unique<wchar_t[]>(wide_len);
+  MultiByteToWideChar(CP_UTF8, 0, path, -1, result.get(), wide_len);
+  return result;
+}
+
 }  // namespace bin
 }  // namespace dart
 
diff --git a/runtime/bin/utils_win.h b/runtime/bin/utils_win.h
index 61a761c890f..21fc212b353 100644
--- a/runtime/bin/utils_win.h
+++ b/runtime/bin/utils_win.h
@@ -5,6 +5,7 @@
 #ifndef RUNTIME_BIN_UTILS_WIN_H_
 #define RUNTIME_BIN_UTILS_WIN_H_
 
+#include <memory>
 #include <utility>
 
 #include "platform/utils.h"
@@ -75,30 +76,7 @@ class WideToUtf8Scope {
   DISALLOW_IMPLICIT_CONSTRUCTORS(WideToUtf8Scope);
 };
 
-class Utf8ToWideScope {
- public:
-  explicit Utf8ToWideScope(const char* utf8, intptr_t length = -1) {
-    int wide_len = MultiByteToWideChar(CP_UTF8, 0, utf8, length, nullptr, 0);
-    wchar_t* wide =
-        reinterpret_cast<wchar_t*>(malloc(sizeof(wchar_t) * wide_len));
-    MultiByteToWideChar(CP_UTF8, 0, utf8, length, wide, wide_len);
-    length_ = wide_len;
-    wide_ = wide;
-  }
-
-  ~Utf8ToWideScope() { free(wide_); }
-
-  wchar_t* wide() const { return wide_; }
-  intptr_t length() const { return length_; }
-  intptr_t size_in_bytes() const { return length_ * sizeof(*wide_); }
-
- private:
-  intptr_t length_;
-  wchar_t* wide_;
-
-  DISALLOW_ALLOCATION();
-  DISALLOW_IMPLICIT_CONSTRUCTORS(Utf8ToWideScope);
-};
+std::unique_ptr<wchar_t[]> Utf8ToWideChar(const char* path);
 
 }  // namespace bin
 }  // namespace dart
diff --git a/runtime/platform/globals.h b/runtime/platform/globals.h
index c9f6dec27ef..29bbb969d1d 100644
--- a/runtime/platform/globals.h
+++ b/runtime/platform/globals.h
@@ -65,6 +65,7 @@
 #endif
 
 #include <intrin.h>
+#define RPC_USE_NATIVE_WCHAR
 #include <rpc.h>
 #include <shellapi.h>
 #include <versionhelpers.h>
diff --git a/tests/standalone/io/directory_test.dart b/tests/standalone/io/directory_test.dart
index 1053368d0ab..e58218943cf 100644
--- a/tests/standalone/io/directory_test.dart
+++ b/tests/standalone/io/directory_test.dart
@@ -251,6 +251,38 @@ class DirectoryTest {
     });
   }
 
+  static void testExistsCreateDeleteWithTrailingBackslashSync() {
+    // Check that adding trailing backslash does not break anything on
+    // Windows.
+    if (!Platform.isWindows) {
+      return;
+    }
+    Directory d = Directory.systemTemp.createTempSync('dart_directory_test');
+    try {
+      Directory d2 = new Directory('${d.path}\\');
+      Expect.isTrue(d.existsSync());
+      Expect.isTrue(d2.existsSync());
+      Directory created1 = new Directory("${d.path}\\subdir\\");
+      Directory created2 = new Directory("${d.path}\\subdir\\subdir\\");
+      created1.createSync();
+      created2.createSync();
+      Expect.isTrue(created1.existsSync());
+      Expect.isTrue(created2.existsSync());
+      created2.deleteSync();
+      created1.deleteSync();
+      Expect.isFalse(created1.existsSync());
+      Expect.isFalse(created2.existsSync());
+      created1.createSync();
+      created2.createSync();
+      created1.deleteSync(recursive: true);
+      Expect.isFalse(created1.existsSync());
+      Expect.isFalse(created2.existsSync());
+    } finally {
+      d.deleteSync(recursive: true);
+      Expect.isFalse(d.existsSync());
+    }
+  }
+
   static void testExistsCreateDeleteSync() {
     Directory d = Directory.systemTemp.createTempSync('dart_directory_test');
     Directory d2 = new Directory('${d.path}/');
@@ -437,6 +469,7 @@ class DirectoryTest {
     testDeleteTooLongNameSync();
     testExistsCreateDelete();
     testExistsCreateDeleteSync();
+    testExistsCreateDeleteWithTrailingBackslashSync();
     testDeleteLinkSync();
     testDeleteLinkAsFileSync();
     testDeleteBrokenLinkAsFileSync();
diff --git a/tests/standalone/io/file_long_path_test.dart b/tests/standalone/io/file_long_path_test.dart
index 2ba7c8e0178..bf82bf310d8 100644
--- a/tests/standalone/io/file_long_path_test.dart
+++ b/tests/standalone/io/file_long_path_test.dart
@@ -6,30 +6,28 @@
 
 import 'dart:io';
 
-import "package:expect/expect.dart";
+import 'package:expect/expect.dart';
+import 'package:path/path.dart' as p;
 
 const maxPath = 260;
 const maxDirectoryPath = maxPath - 12;
 String longName = '${'x' * 248}';
 
-Directory createLongPathDir(Directory tmp) {
-  if (tmp.path.length <= maxDirectoryPath) {
-    var path = tmp.path;
-    path += '\\${'t' * 248}';
-    var dir = Directory(path);
-    dir.createSync(recursive: true);
-    // Test the rename() of directory
-    dir = dir.renameSync(tmp.path + '\\$longName');
-    Expect.isTrue(dir.existsSync());
-    Expect.isFalse(Directory(path).existsSync());
-    return dir;
-  } else {
-    return tmp;
-  }
+Directory createLongPathDir(Directory tmp, [String? suffix]) {
+  var path = tmp.path;
+  path = p.join(path, 't' * 248);
+  var dir = Directory(path);
+  dir.createSync(recursive: true);
+  Expect.isTrue(dir.existsSync());
+  // Test the rename() of directory
+  dir = dir.renameSync(p.join(tmp.path, '$longName$suffix'));
+  Expect.isTrue(dir.existsSync());
+  Expect.isFalse(Directory(path).existsSync());
+  return dir;
 }
 
 void testCreate(String dir) {
-  final path = '${dir}\\a_long_path_filename';
+  final path = p.join(dir, 'a_long_path_filename');
   Expect.isTrue(path.length > maxPath);
   final file = File(path);
   file.createSync();
@@ -38,8 +36,8 @@ void testCreate(String dir) {
 }
 
 void testCopy(String dir) {
-  final src = '${dir}\\a_long_path_filename_1';
-  final dest = '${dir}\\a_long_path_filename_2';
+  final src = p.join(dir, 'a_long_path_filename_1');
+  final dest = p.join(dir, 'a_long_path_filename_2');
   Expect.isTrue(src.length > maxPath);
   final file1 = File(src);
   file1.createSync();
@@ -51,7 +49,7 @@ void testCopy(String dir) {
 }
 
 void testRename(String dir) {
-  final path = '${dir}\\a_long_path_filename';
+  final path = p.join(dir, 'a_long_path_filename');
   Expect.isTrue(path.length > maxPath);
   final file = File(path);
   file.createSync();
@@ -65,7 +63,7 @@ void testRename(String dir) {
 }
 
 void testReadWrite(String dir) {
-  final path = '${dir}\\a_long_path_filename';
+  final path = p.join(dir, 'a_long_path_filename');
   Expect.isTrue(path.length > maxPath);
   final file = File(path);
 
@@ -82,7 +80,7 @@ void testReadWrite(String dir) {
 }
 
 void testOpen(String dir) {
-  final path = '${dir}\\a_long_path_filename';
+  final path = p.join(dir, 'a_long_path_filename');
   Expect.isTrue(path.length > maxPath);
   final file = File(path);
   file.createSync();
@@ -91,7 +89,7 @@ void testOpen(String dir) {
 }
 
 void testFileStat(String dir) {
-  final path = '${dir}\\a_long_path_filename';
+  final path = p.join(dir, 'a_long_path_filename');
   Expect.isTrue(path.length > maxPath);
   final file = File(path);
   file.createSync();
@@ -108,21 +106,37 @@ void testFileStat(String dir) {
       stat.accessed.toString(), file.lastAccessedSync().toString());
 }
 
-void testCreateLinkToDir(String dir) {
-  final linkPath = '$dir\\a_long_path_linkname';
-  final renamedPath = '$dir\\a_long_renamed_path_linkname';
+String _createDirectoryHelper(String currentDir, String targetDir) {
+  if (p.isRelative(targetDir)) {
+    targetDir = p.normalize(p.absolute(currentDir, targetDir));
+  }
+  final dir = Directory(targetDir)..createSync();
+  Expect.isTrue(dir.existsSync());
+  return dir.path;
+}
+
+void testCreateLinkToDir(String dir, String dir2) {
+  final linkPath = p.join(dir, 'a_long_path_linkname');
+  final renamedPath = p.join(dir, 'a_long_renamed_path_linkname');
 
   Expect.isTrue(linkPath.length > maxPath);
   Expect.isTrue(renamedPath.length > maxPath);
 
-  var targetDirectory1 = '$dir\\a_long_directory_target1';
-  var targetDirectory2 = '$dir\\a_long_directory_target2';
+  final targetDirectory1 =
+      _createDirectoryHelper(dir, p.join(dir2, 'a_long_directory_target1'));
+  final targetDirectory2 =
+      _createDirectoryHelper(dir, p.join(dir2, 'a_long_directory_target2'));
 
-  Directory(targetDirectory1).createSync();
-  Directory(targetDirectory2).createSync();
+  final linkTarget1 = p.isRelative(dir2)
+      ? p.relative(targetDirectory1, from: p.dirname(p.absolute(linkPath)))
+      : targetDirectory1;
+
+  final linkTarget2 = p.isRelative(dir2)
+      ? p.relative(targetDirectory2, from: p.dirname(p.absolute(linkPath)))
+      : targetDirectory2;
 
   // Create link
-  final link = Link(linkPath)..createSync(targetDirectory1);
+  final link = Link(linkPath)..createSync(linkTarget1);
   Expect.isTrue(link.existsSync());
   final resolvedCreatePath = link.resolveSymbolicLinksSync();
   Expect.isTrue(
@@ -139,7 +153,7 @@ void testCreateLinkToDir(String dir) {
       '${link.path} should resolve to $targetDirectory1 but resolved to $resolvedRenamePath');
 
   // Update link target
-  renamedLink.updateSync(targetDirectory2);
+  renamedLink.updateSync(linkTarget2);
   final resolvedUpdatedPath = renamedLink.resolveSymbolicLinksSync();
   Expect.isTrue(
       FileSystemEntity.identicalSync(targetDirectory2, resolvedUpdatedPath),
@@ -150,11 +164,30 @@ void testCreateLinkToDir(String dir) {
   renamedLink.deleteSync();
 }
 
-void testCreateLinkToFile(String dir) {
-  final path = '${dir}\\a_long_path_linkname';
+void testCreateLinkToFile(String dir, String dir2) {
+  final path = p.join(dir, 'a_long_path_linkname');
   Expect.isTrue(path.length > maxPath);
-  var target = '$dir\\a_long_path_target';
-  final link = Link(path)..createSync(target);
+
+  String _pathHelper(String currentDir, String targetPath) {
+    if (p.isRelative(targetPath)) {
+      return p.normalize(p.absolute(currentDir, targetPath));
+    } else {
+      return targetPath;
+    }
+  }
+
+  var target = _pathHelper(dir, p.join(dir2, 'a_long_path_target'));
+  var target2 = _pathHelper(dir, p.join(dir2, 'an_updated_target'));
+
+  var linkTarget = p.isRelative(dir2)
+      ? p.relative(target, from: p.dirname(p.absolute(path)))
+      : target;
+
+  var linkTarget2 = p.isRelative(dir2)
+      ? p.relative(target2, from: p.dirname(p.absolute(path)))
+      : target2;
+
+  final link = Link(path)..createSync(linkTarget);
 
   final dest = File(target)..createSync();
   Expect.isTrue(dest.existsSync());
@@ -165,15 +198,14 @@ void testCreateLinkToFile(String dir) {
       '${link.path} should resolve to $target but resolved to $resolvedPath');
 
   // Rename link
-  var renamedLink = link.renameSync('${dir}\\a_renamed_long_path_link');
+  var renamedLink = link.renameSync(p.join(dir, 'a_renamed_long_path_link'));
   Expect.isTrue(renamedLink.existsSync());
   Expect.isFalse(link.existsSync());
   Expect.isTrue(renamedLink.targetSync().contains('a_long_path_target'));
 
   // Update link target
-  target = '$dir\\an_updated_target';
-  final renamedDest = File(target)..createSync();
-  renamedLink.updateSync(target);
+  final renamedDest = File(target2)..createSync();
+  renamedLink.updateSync(linkTarget2);
   Expect.isTrue(renamedLink.targetSync().contains('an_updated_target'));
 
   dest.deleteSync();
@@ -182,8 +214,8 @@ void testCreateLinkToFile(String dir) {
 }
 
 testNormalLinkToLongPath(String short, String long) {
-  var target = File('$long\\file_target')..createSync();
-  final link = Link('$short\\link')..createSync(target.path);
+  var target = File(p.join(long, 'file_target'))..createSync();
+  final link = Link(p.join(short, 'link'))..createSync(target.path);
   Expect.isTrue(target.path.length > maxPath);
   Expect.isTrue(link.resolveSymbolicLinksSync().length > maxPath);
   Expect.isTrue(link.path.length < maxPath);
@@ -192,7 +224,7 @@ testNormalLinkToLongPath(String short, String long) {
   Expect.isTrue(link.existsSync());
   Expect.equals(target.path, link.targetSync());
 
-  var targetDir = Directory('$long\\dir_target')..createSync();
+  var targetDir = Directory(p.join(long, 'dir_target'))..createSync();
   link.updateSync(targetDir.path);
   Expect.equals(targetDir.path, link.targetSync());
 
@@ -202,8 +234,8 @@ testNormalLinkToLongPath(String short, String long) {
 }
 
 testLongPathLinkToNormal(String short, String long) {
-  var target = File('$short\\file_target')..createSync();
-  final link = Link('$long\\link')..createSync(target.path);
+  var target = File(p.join(short, 'file_target'))..createSync();
+  final link = Link(p.join(long, 'link'))..createSync(target.path);
 
   Expect.isTrue(target.path.length < maxPath);
   Expect.isTrue(link.path.length > maxPath);
@@ -212,7 +244,7 @@ testLongPathLinkToNormal(String short, String long) {
   Expect.isTrue(link.existsSync());
   Expect.equals(target.path, link.targetSync());
 
-  var targetDir = Directory('$short\\dir_target')..createSync();
+  var targetDir = Directory(p.join(short, 'dir_target'))..createSync();
   link.updateSync(targetDir.path);
   Expect.equals(targetDir.path, link.targetSync());
 
@@ -221,38 +253,49 @@ testLongPathLinkToNormal(String short, String long) {
   targetDir.deleteSync();
 }
 
-testDirectorySetCurrent(String dir) {
+testDirectorySetCurrentFails(String dir) {
   // This tests setting a long path directory to current directory.
-  // This will fail.
   Expect.isTrue(dir.length > maxPath);
-  Expect.throws<FileSystemException>(() {
-    Directory.current = dir;
-  }, (e) => e.toString().contains('extension is too long'));
+  if (Platform.isWindows) {
+    // On Windows current directory path is limited to MAX_PATH characters.
+    // Windows 10, Version 1607 introduced a way to lift this limitation but
+    // it requires opt-in from both application and the OS configuration.
+    //
+    // 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
+    Expect.throws<FileSystemException>(() {
+      Directory.current = dir;
+    }, (e) => e.toString().contains('extension is too long'));
+  }
 }
 
 void main() {
-  if (!Platform.isWindows) {
-    return;
-  }
-  final tmp = Directory.systemTemp.createTempSync('dart-file-long-path');
+  final tmp = Directory.systemTemp.createTempSync('flpt');
   final oldCurrent = Directory.current;
   Directory.current = tmp;
   try {
-    String dir = createLongPathDir(tmp).path;
-    testDirectorySetCurrent(dir);
-    for (final path in [dir, ".\\$longName", ".\\$longName\\..\\$longName"]) {
+    String dir1 = createLongPathDir(tmp, 'dir1').path;
+    String dir2 = createLongPathDir(tmp, 'dir2').path;
+    testDirectorySetCurrentFails(dir1);
+    for (final path in [
+      dir1,
+      p.join('.', '${longName}dir1'),
+      p.join('.', '${longName}dir1', '..', '${longName}dir1'),
+    ]) {
       testCreate(path);
       testCopy(path);
       testRename(path);
       testReadWrite(path);
       testOpen(path);
       testFileStat(path);
-      testCreateLinkToDir(path);
-      testCreateLinkToFile(path);
+      for (var relative in [true, false]) {
+        final targetDir = relative ? p.relative(dir2, from: dir1) : dir2;
+        testCreateLinkToDir(path, targetDir);
+        testCreateLinkToFile(path, targetDir);
+      }
     }
 
-    testNormalLinkToLongPath(tmp.path, dir);
-    testLongPathLinkToNormal(tmp.path, dir);
+    testNormalLinkToLongPath(tmp.path, dir1);
+    testLongPathLinkToNormal(tmp.path, dir1);
   } finally {
     // Reset the current Directory.
     Directory.current = oldCurrent;