diff --git a/CHANGELOG.md b/CHANGELOG.md
index 87f7b1f0711..50e71af4a31 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -47,6 +47,18 @@
 *   **Breaking change:** The `klass` getter on the `InstanceConstant` class in
     the Kernel AST API has been renamed to `classNode` for consistency.
 
+*   **Breaking change:** Updated `Link` implementation to utilize true symbolic
+    links instead of junctions on Windows. Existing junctions will continue to
+    work with the new `Link` implementation, but all new links will create
+    symbolic links.
+    
+    To create a symbolic link, Dart must be run with
+    administrative privileges or Developer Mode must be enabled, otherwise a
+    `FileSystemException` will be raised with errno set to
+    `ERROR_PRIVILEGE_NOT_HELD` (Issue [33966]).
+
+[33966]: https://github.com/dart-lang/sdk/issues/33966
+
 ### Dart VM
 
 ### Tool Changes
diff --git a/runtime/bin/file_win.cc b/runtime/bin/file_win.cc
index d7d5b3f84bf..0b59b20303b 100644
--- a/runtime/bin/file_win.cc
+++ b/runtime/bin/file_win.cc
@@ -375,63 +375,32 @@ typedef struct _REPARSE_DATA_BUFFER {
 static const int kReparseDataHeaderSize = sizeof ULONG + 2 * sizeof USHORT;
 static const int kMountPointHeaderSize = 4 * sizeof USHORT;
 
+// Note: CreateLink used to create junctions on Windows instead of true
+// symbolic links. All File::*Link methods now support handling links created
+// as junctions and symbolic links.
 bool File::CreateLink(Namespace* namespc,
                       const char* utf8_name,
                       const char* utf8_target) {
   Utf8ToWideScope name(utf8_name);
-  int create_status = CreateDirectoryW(name.wide(), NULL);
-  // If the directory already existed, treat it as a success.
-  if ((create_status == 0) &&
-      ((GetLastError() != ERROR_ALREADY_EXISTS) ||
-       ((GetFileAttributesW(name.wide()) & FILE_ATTRIBUTE_DIRECTORY) != 0))) {
-    return false;
-  }
-
-  HANDLE dir_handle = CreateFileW(
-      name.wide(), GENERIC_READ | GENERIC_WRITE,
-      FILE_SHARE_READ | FILE_SHARE_WRITE | FILE_SHARE_DELETE, NULL,
-      OPEN_EXISTING, FILE_FLAG_BACKUP_SEMANTICS | FILE_FLAG_OPEN_REPARSE_POINT,
-      NULL);
-  if (dir_handle == INVALID_HANDLE_VALUE) {
-    return false;
-  }
-
   Utf8ToWideScope target(utf8_target);
-  int target_len = wcslen(target.wide());
-  if (target_len > MAX_PATH - 1) {
-    CloseHandle(dir_handle);
-    return false;
+  DWORD flags = SYMBOLIC_LINK_FLAG_ALLOW_UNPRIVILEGED_CREATE;
+
+  File::Type type = File::GetType(namespc, utf8_target, true);
+  if (type == kIsDirectory) {
+    flags |= SYMBOLIC_LINK_FLAG_DIRECTORY;
   }
 
-  int reparse_data_buffer_size =
-      sizeof REPARSE_DATA_BUFFER + 2 * MAX_PATH * sizeof WCHAR;
-  REPARSE_DATA_BUFFER* reparse_data_buffer =
-      reinterpret_cast<REPARSE_DATA_BUFFER*>(malloc(reparse_data_buffer_size));
-  reparse_data_buffer->ReparseTag = IO_REPARSE_TAG_MOUNT_POINT;
-  wcscpy(reparse_data_buffer->MountPointReparseBuffer.PathBuffer,
-         target.wide());
-  wcscpy(
-      reparse_data_buffer->MountPointReparseBuffer.PathBuffer + target_len + 1,
-      target.wide());
-  reparse_data_buffer->MountPointReparseBuffer.SubstituteNameOffset = 0;
-  reparse_data_buffer->MountPointReparseBuffer.SubstituteNameLength =
-      target_len * sizeof WCHAR;
-  reparse_data_buffer->MountPointReparseBuffer.PrintNameOffset =
-      (target_len + 1) * sizeof WCHAR;
-  reparse_data_buffer->MountPointReparseBuffer.PrintNameLength =
-      target_len * sizeof WCHAR;
-  reparse_data_buffer->ReparseDataLength =
-      (target_len + 1) * 2 * sizeof WCHAR + kMountPointHeaderSize;
-  DWORD dummy_received_bytes;
-  int result = DeviceIoControl(
-      dir_handle, FSCTL_SET_REPARSE_POINT, reparse_data_buffer,
-      reparse_data_buffer->ReparseDataLength + kReparseDataHeaderSize, NULL, 0,
-      &dummy_received_bytes, NULL);
-  free(reparse_data_buffer);
-  if (CloseHandle(dir_handle) == 0) {
-    return false;
+  int create_status = CreateSymbolicLinkW(name.wide(), target.wide(), 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);
   }
-  return (result != 0);
+
+  return (create_status != 0);
 }
 
 bool File::Delete(Namespace* namespc, const char* name) {
@@ -444,12 +413,18 @@ bool File::DeleteLink(Namespace* namespc, const char* name) {
   Utf8ToWideScope system_name(name);
   bool result = false;
   DWORD attributes = GetFileAttributesW(system_name.wide());
-  if ((attributes != INVALID_FILE_ATTRIBUTES) &&
-      (attributes & FILE_ATTRIBUTE_REPARSE_POINT) != 0) {
-    // It's a junction(link), delete it.
+  if ((attributes == INVALID_FILE_ATTRIBUTES) ||
+      ((attributes & FILE_ATTRIBUTE_REPARSE_POINT) == 0)) {
+    SetLastError(ERROR_NOT_A_REPARSE_POINT);
+    return false;
+  }
+  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);
   } else {
-    SetLastError(ERROR_NOT_A_REPARSE_POINT);
+    // Symbolic link to a file. Remove the file.
+    result = (DeleteFileW(system_name.wide()) != 0);
   }
   return result;
 }
@@ -458,65 +433,59 @@ bool File::Rename(Namespace* namespc,
                   const char* old_path,
                   const char* new_path) {
   File::Type type = GetType(namespc, old_path, false);
-  if (type == kIsFile) {
-    Utf8ToWideScope system_old_path(old_path);
-    Utf8ToWideScope system_new_path(new_path);
-    DWORD flags = MOVEFILE_WRITE_THROUGH | MOVEFILE_REPLACE_EXISTING;
-    int move_status =
-        MoveFileExW(system_old_path.wide(), system_new_path.wide(), flags);
-    return (move_status != 0);
-  } else {
+  if (type != kIsFile) {
     SetLastError(ERROR_FILE_NOT_FOUND);
+    return false;
   }
-  return false;
+  Utf8ToWideScope system_old_path(old_path);
+  Utf8ToWideScope system_new_path(new_path);
+  DWORD flags = MOVEFILE_WRITE_THROUGH | MOVEFILE_REPLACE_EXISTING;
+  int move_status =
+      MoveFileExW(system_old_path.wide(), system_new_path.wide(), flags);
+  return (move_status != 0);
 }
 
 bool File::RenameLink(Namespace* namespc,
                       const char* old_path,
                       const char* new_path) {
   File::Type type = GetType(namespc, old_path, false);
-  if (type == kIsLink) {
-    Utf8ToWideScope system_old_path(old_path);
-    Utf8ToWideScope system_new_path(new_path);
-    DWORD flags = MOVEFILE_WRITE_THROUGH | MOVEFILE_REPLACE_EXISTING;
-    // Links 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 a link.
-    if (Directory::Exists(namespc, new_path) == Directory::EXISTS) {
-      bool result = true;
-      if (GetType(namespc, new_path, false) == kIsLink) {
-        result = DeleteLink(namespc, new_path);
-      } else {
-        result = Delete(namespc, new_path);
-      }
-      // Bail out if the Delete calls fail.
-      if (!result) {
-        return false;
-      }
-    }
-    int move_status =
-        MoveFileExW(system_old_path.wide(), system_new_path.wide(), flags);
-    return (move_status != 0);
-  } else {
+  if (type != kIsLink) {
     SetLastError(ERROR_FILE_NOT_FOUND);
+    return false;
   }
-  return false;
+  Utf8ToWideScope system_old_path(old_path);
+  Utf8ToWideScope system_new_path(new_path);
+  DWORD flags = MOVEFILE_WRITE_THROUGH | MOVEFILE_REPLACE_EXISTING;
+
+  // Junction links 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 a link. This step is only
+  // necessary for junctions created by the old Link.create implementation.
+  if ((Directory::Exists(namespc, new_path) == Directory::EXISTS) &&
+      (GetType(namespc, new_path, false) == kIsLink)) {
+    // Bail out if the DeleteLink call fails.
+    if (!DeleteLink(namespc, new_path)) {
+      return false;
+    }
+  }
+  int move_status =
+      MoveFileExW(system_old_path.wide(), system_new_path.wide(), flags);
+  return (move_status != 0);
 }
 
 bool File::Copy(Namespace* namespc,
                 const char* old_path,
                 const char* new_path) {
   File::Type type = GetType(namespc, old_path, false);
-  if (type == kIsFile) {
-    Utf8ToWideScope system_old_path(old_path);
-    Utf8ToWideScope system_new_path(new_path);
-    bool success = CopyFileExW(system_old_path.wide(), system_new_path.wide(),
-                               NULL, NULL, NULL, 0) != 0;
-    return success;
-  } else {
+  if (type != kIsFile) {
     SetLastError(ERROR_FILE_NOT_FOUND);
+    return false;
   }
-  return false;
+  Utf8ToWideScope system_old_path(old_path);
+  Utf8ToWideScope system_new_path(new_path);
+  bool success = CopyFileExW(system_old_path.wide(), system_new_path.wide(),
+                             NULL, NULL, NULL, 0) != 0;
+  return success;
 }
 
 int64_t File::LengthFromPath(Namespace* namespc, const char* name) {
diff --git a/sdk/lib/io/link.dart b/sdk/lib/io/link.dart
index b43c13a8106..79f865638da 100644
--- a/sdk/lib/io/link.dart
+++ b/sdk/lib/io/link.dart
@@ -50,11 +50,11 @@ abstract class Link implements FileSystemEntity {
    * components are created. The directories in the path of [target] are
    * not affected, unless they are also in [path].
    *
-   * On the Windows platform, this will only work with directories, and the
-   * target directory must exist. The link will be created as a Junction.
-   * Only absolute links will be created, and relative paths to the target
-   * will be converted to absolute paths by joining them with the path of the
-   * directory the link is contained in.
+   * On the Windows platform, this call will create a true symbolic link
+   * instead of a Junction. In order to create a symbolic link on Windows, Dart
+   * must be run in Administrator mode or the system must have Developer Mode
+   * enabled, otherwise a [FileSystemException] will be raised with 
+   * `ERROR_PRIVILEGE_NOT_HELD` set as the errno when this call is made.
    *
    * On other platforms, the posix symlink() call is used to make a symbolic
    * link containing the string [target].  If [target] is a relative path,
@@ -71,10 +71,11 @@ abstract class Link implements FileSystemEntity {
    * non-existing path components are created. The directories in
    * the path of [target] are not affected, unless they are also in [path].
    *
-   * On the Windows platform, this will only work with directories, and the
-   * target directory must exist. The link will be created as a Junction.
-   * Only absolute links will be created, and relative paths to the target
-   * will be converted to absolute paths.
+   * On the Windows platform, this call will create a true symbolic link
+   * instead of a Junction. In order to create a symbolic link on Windows, Dart
+   * must be run in Administrator mode or the system must have Developer Mode
+   * enabled, otherwise a [FileSystemException] will be raised with 
+   * `ERROR_PRIVILEGE_NOT_HELD` set as the errno when this call is made.
    *
    * On other platforms, the posix symlink() call is used to make a symbolic
    * link containing the string [target].  If [target] is a relative path,
@@ -85,9 +86,6 @@ abstract class Link implements FileSystemEntity {
   /**
    * Synchronously updates the link. Calling [updateSync] on a non-existing link
    * will throw an exception.
-   *
-   * On the Windows platform, this will only work with directories, and the
-   * target directory must exist.
    */
   void updateSync(String target);
 
@@ -95,9 +93,6 @@ abstract class Link implements FileSystemEntity {
    * Updates the link. Returns a [:Future<Link>:] that completes with the
    * link when it has been updated.  Calling [update] on a non-existing link
    * will complete its returned future with an exception.
-   *
-   * On the Windows platform, this will only work with directories, and the
-   * target directory must exist.
    */
   Future<Link> update(String target);
 
@@ -183,9 +178,6 @@ class _Link extends FileSystemEntity implements Link {
   Link get absolute => new Link.fromRawPath(_rawAbsolutePath);
 
   Future<Link> create(String target, {bool recursive: false}) {
-    if (Platform.isWindows) {
-      target = _makeWindowsLinkTarget(target);
-    }
     var result =
         recursive ? parent.create(recursive: true) : new Future.value(null);
     return result
@@ -204,28 +196,10 @@ class _Link extends FileSystemEntity implements Link {
     if (recursive) {
       parent.createSync(recursive: true);
     }
-    if (Platform.isWindows) {
-      target = _makeWindowsLinkTarget(target);
-    }
     var result = _File._createLink(_Namespace._namespace, _rawPath, target);
     throwIfError(result, "Cannot create link", path);
   }
 
-  // Put target into the form "\??\C:\my\target\dir".
-  String _makeWindowsLinkTarget(String target) {
-    Uri base = new Uri.file('${Directory.current.path}\\');
-    Uri link = new Uri.file(path);
-    Uri destination = new Uri.file(target);
-    String result = base.resolveUri(link).resolveUri(destination).toFilePath();
-    if (result.length > 3 && result[1] == ':' && result[2] == '\\') {
-      return '\\??\\$result';
-    } else {
-      throw new FileSystemException(
-          'Target $result of Link.create on Windows cannot be converted'
-          ' to start with a drive letter.  Unexpected error.');
-    }
-  }
-
   void updateSync(String target) {
     // TODO(12414): Replace with atomic update, where supported by platform.
     // Atomically changing a link can be done by creating the new link, with
diff --git a/tests/standalone_2/io/link_test.dart b/tests/standalone_2/io/link_test.dart
index afc0f73cf0c..477d7b53de1 100644
--- a/tests/standalone_2/io/link_test.dart
+++ b/tests/standalone_2/io/link_test.dart
@@ -7,7 +7,6 @@ import "package:expect/expect.dart";
 import "package:path/path.dart";
 import "dart:async";
 import "dart:io";
-import "dart:isolate";
 
 // Test the dart:io Link class.
 
@@ -57,8 +56,8 @@ testCreateSync() {
 
   // Test FileSystemEntity.identical on files, directories, and links,
   // reached by different paths.
-  Expect
-      .isTrue(FileSystemEntity.identicalSync(createdDirectly, createdDirectly));
+  Expect.isTrue(
+      FileSystemEntity.identicalSync(createdDirectly, createdDirectly));
   Expect.isFalse(
       FileSystemEntity.identicalSync(createdDirectly, createdThroughLink));
   Expect.isTrue(FileSystemEntity.identicalSync(
@@ -190,6 +189,38 @@ testRenameSync() {
     Expect.isFalse(link2.existsSync());
   }
 
+  testRenameToLink(String base, String target) {
+    Link link1 = Link(join(base, '1'))..createSync(target);
+    Link link2 = Link(join(base, '2'))..createSync(target);
+    Expect.isTrue(link1.existsSync());
+    Expect.isTrue(link2.existsSync());
+    Link renamed = link1.renameSync(link2.path);
+    Expect.isFalse(link1.existsSync());
+    Expect.isTrue(renamed.existsSync());
+    renamed.deleteSync();
+    Expect.isFalse(renamed.existsSync());
+  }
+
+  testRenameToTarget(String linkName, String target, bool isDirectory) {
+    Link link = Link(linkName)..createSync(target);
+    Expect.isTrue(link.existsSync());
+    try {
+      Link renamed = link.renameSync(target);
+      if (isDirectory) {
+        Expect.fail('Renaming a link to the name of an existing directory ' +
+            'should fail');
+      }
+      Expect.isTrue(renamed.existsSync());
+      renamed.deleteSync();
+    } on FileSystemException catch (_) {
+      if (isDirectory) {
+        return;
+      }
+      Expect.fail('Renaming a link to the name of an existing file should ' +
+          'not fail');
+    }
+  }
+
   Directory baseDir = Directory.systemTemp.createTempSync('dart_link');
   String base = baseDir.path;
   Directory dir = new Directory(join(base, 'a'))..createSync();
@@ -198,6 +229,11 @@ testRenameSync() {
   testRename(base, file.path);
   testRename(base, dir.path);
 
+  testRenameToLink(base, file.path);
+
+  testRenameToTarget(join(base, 'fileLink'), file.path, false);
+  testRenameToTarget(join(base, 'dirLink'), dir.path, true);
+
   baseDir.deleteSync(recursive: true);
 }