diff --git a/LibTest/io/Link/createSync_A04_t05.dart b/LibTest/io/Link/createSync_A04_t05.dart
new file mode 100644
index 0000000000..3b1e21788b
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t05.dart
@@ -0,0 +1,60 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if `target` exists then the type of the link will
+/// match the type `target`. Test [Link] pointing to a not existing entity as a
+/// target (expect `file` on Windows and `notFound` on other platforms).
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  Link target = getTempLinkSync(
+      parent: sandbox, target: getTempFilePath(parent: sandbox));
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target.path);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+    File file = File(link.targetSync());
+    file.createSync();
+    Expect.equals(
+        FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A04_t06.dart b/LibTest/io/Link/createSync_A04_t06.dart
new file mode 100644
index 0000000000..5bc13a5089
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t06.dart
@@ -0,0 +1,57 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if `target` does not exist then the type of the link
+/// will be `file` on Windows and `notFound` on other platforms.
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(getTempFilePath(parent: sandbox));
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+    File file = File(link.targetSync());
+    file.createSync();
+    Expect.equals(
+        FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A04_t07.dart b/LibTest/io/Link/createSync_A04_t07.dart
new file mode 100644
index 0000000000..5f261fff5d
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t07.dart
@@ -0,0 +1,68 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target directory was created and
+/// then this directory was deleted and created again, then the link stays valid
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  Directory target1 = getTempDirectorySync(parent: sandbox);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  Directory target2 = Directory(target1.path);
+  target2.createSync();
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  Directory linkTarget = getTempDirectorySync();
+  target3.createSync(linkTarget.path);
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+}
diff --git a/LibTest/io/Link/createSync_A04_t08.dart b/LibTest/io/Link/createSync_A04_t08.dart
new file mode 100644
index 0000000000..e784024a7f
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t08.dart
@@ -0,0 +1,79 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target directory was created and
+/// then this directory was deleted and a file with the same name created, then
+/// on Windows the link became invalid on other platforms it changes its type
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  Directory target1 = getTempDirectorySync(parent: sandbox);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  File target2 = File(target1.path);
+  target2.createSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  }
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  File linkTarget = getTempFileSync();
+  target3.createSync(linkTarget.path);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A04_t09.dart b/LibTest/io/Link/createSync_A04_t09.dart
new file mode 100644
index 0000000000..0fbfc8b69d
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t09.dart
@@ -0,0 +1,68 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target file was created and
+/// then this file was deleted and created again, then the link stays valid
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  File target1 = getTempFileSync(parent: sandbox);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  File target2 = File(target1.path);
+  target2.createSync();
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  File linkTarget = getTempFileSync();
+  target3.createSync(linkTarget.path);
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+}
diff --git a/LibTest/io/Link/createSync_A04_t10.dart b/LibTest/io/Link/createSync_A04_t10.dart
new file mode 100644
index 0000000000..ba1fffaa29
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t10.dart
@@ -0,0 +1,79 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target file was created and then
+/// this file was deleted and a directory with the same name created, then
+/// on Windows the link became invalid on other platforms it changes its type
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  File target1 = getTempFileSync(parent: sandbox);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  Directory target2 = Directory(target1.path);
+  target2.createSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  }
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  Directory linkTarget = getTempDirectorySync();
+  target3.createSync(linkTarget.path);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A04_t11.dart b/LibTest/io/Link/createSync_A04_t11.dart
new file mode 100644
index 0000000000..eb69965e52
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t11.dart
@@ -0,0 +1,69 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target another link pointing to
+/// a directory was created and then this link was deleted and created again,
+/// then the first link stays valid
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  Directory linkTarget = getTempDirectorySync(parent: sandbox);
+  Link target1 = getTempLinkSync(parent: sandbox, target: linkTarget.path);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  Directory target2 = Directory(target1.path);
+  target2.createSync();
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  target3.createSync(sandbox.path);
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+}
diff --git a/LibTest/io/Link/createSync_A04_t12.dart b/LibTest/io/Link/createSync_A04_t12.dart
new file mode 100644
index 0000000000..bade7305c1
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t12.dart
@@ -0,0 +1,81 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target another link pointing to
+/// a directory was created and then this link was deleted and a file with the
+/// same path or link to a file created again, then the first link became
+/// invalid on Windows and changes its type on other platforms
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  Directory linkTarget = getTempDirectorySync();
+  Link target1 = getTempLinkSync(parent: sandbox, target: linkTarget.path);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  File target2 = File(target1.path);
+  target2.createSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  }
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  File linkTarget3 = getTempFileSync();
+  target3.createSync(linkTarget3.path);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A04_t13.dart b/LibTest/io/Link/createSync_A04_t13.dart
new file mode 100644
index 0000000000..9b73b729f7
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t13.dart
@@ -0,0 +1,70 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target another link pointing to
+/// a file was created and then this link was deleted and created again, then
+/// the link stays valid
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  File linkTarget = getTempFileSync(parent: sandbox);
+  Link target1 = getTempLinkSync(parent: sandbox, target: linkTarget.path);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(FileSystemEntityType.notFound,
+        FileSystemEntity.typeSync(link.path));
+  }
+  File target2 = File(target1.path);
+  target2.createSync();
+  Expect.equals(FileSystemEntityType.file,
+      FileSystemEntity.typeSync(link.path));
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  File linkTarget3 = getTempFileSync();
+  target3.createSync(linkTarget3.path);
+  Expect.equals(FileSystemEntityType.file,
+      FileSystemEntity.typeSync(link.path));
+}
diff --git a/LibTest/io/Link/createSync_A04_t14.dart b/LibTest/io/Link/createSync_A04_t14.dart
new file mode 100644
index 0000000000..41e160390a
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t14.dart
@@ -0,0 +1,81 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the target another link pointing to
+/// a file was created and then this link was deleted and a directory with the
+/// same name created, then on Windows the link became invalid on other
+/// platforms it changes its type
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  File linkTarget = getTempFileSync(parent: sandbox);
+  Link target1 = getTempLinkSync(parent: sandbox, target: linkTarget.path);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(target1.path);
+  Expect.equals(FileSystemEntityType.file,
+      FileSystemEntity.typeSync(link.path));
+  target1.deleteSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(FileSystemEntityType.notFound,
+        FileSystemEntity.typeSync(link.path));
+  }
+  Directory target2 = Directory(target1.path);
+  target2.createSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(FileSystemEntityType.directory,
+        FileSystemEntity.typeSync(link.path));
+  }
+  target2.deleteSync();
+
+  Link target3 = Link(target1.path);
+  Directory linkTarget3 = getTempDirectorySync();
+  target3.createSync(linkTarget3.path);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(FileSystemEntityType.directory,
+        FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A04_t15.dart b/LibTest/io/Link/createSync_A04_t15.dart
new file mode 100644
index 0000000000..8e5ce72513
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t15.dart
@@ -0,0 +1,65 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the not existing target was created
+/// and then a file on the link's target was created, then the link became valid
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String linkTarget = getTempFilePath(parent: sandbox);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(linkTarget);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  File target2 = File(linkTarget);
+  target2.createSync();
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  target2.deleteSync();
+
+  Link target3 = Link(linkTarget);
+  File _linkTarget = getTempFileSync();
+  target3.createSync(_linkTarget.path);
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+}
diff --git a/LibTest/io/Link/createSync_A04_t16.dart b/LibTest/io/Link/createSync_A04_t16.dart
new file mode 100644
index 0000000000..4afb8658a7
--- /dev/null
+++ b/LibTest/io/Link/createSync_A04_t16.dart
@@ -0,0 +1,75 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that if a link with the not existing target was created
+/// and then a directory on the link's target was created, then the link become
+/// invalid on Windows and changes its type on other platforms
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String linkTarget = getTempFilePath(parent: sandbox);
+  Link link = Link(getTempFilePath(parent: sandbox));
+  link.createSync(linkTarget);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  Directory target2 = Directory(linkTarget);
+  target2.createSync();
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  }
+  target2.deleteSync();
+
+  Link target3 = Link(linkTarget);
+  target3.createSync(sandbox.path);
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A05_t01.dart b/LibTest/io/Link/createSync_A05_t01.dart
index 934233ef8a..e1f2d94ab8 100644
--- a/LibTest/io/Link/createSync_A05_t01.dart
+++ b/LibTest/io/Link/createSync_A05_t01.dart
@@ -3,35 +3,33 @@
 // BSD-style license that can be found in the LICENSE file.
 
 /// @assertion void createSync(
-///  String target, {
-///  bool recursive: false
-///  })
+///   String target,
+///   {bool recursive = false}
+/// )
 ///  Synchronously create the link. Calling createSync on an existing link will
 ///  throw an exception.
 ///
-///  If recursive is false, the default, the link is created only if all
-///  directories in its path exist. If recursive is true, all non-existing path
-///  components are created. The directories in the path of target are not
-///  affected, unless they are also in path.
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
 ///
-///  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 the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
 ///
-///  On other platforms, the posix symlink() call is used to make a symbolic link
-///  containing the string target. If target is a relative path, it will be
-///  interpreted relative to the directory containing the link.
-/// @description Checks that on the Windows platform relative paths to the target
-/// is not converted to absolute paths (as it was in the past)
-///
-/// @note The test should run with the Administrator priveleges on Windows.
-/// Dart API Spec reads:
 /// 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.
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that on the Windows platform relative paths to the
+/// target is not converted to absolute paths (as it was in the past)
 ///
 /// @author sgrekhov@unipro.ru
 
diff --git a/LibTest/io/Link/createSync_A06_t01.dart b/LibTest/io/Link/createSync_A06_t01.dart
index e4faa06870..8d0759f275 100644
--- a/LibTest/io/Link/createSync_A06_t01.dart
+++ b/LibTest/io/Link/createSync_A06_t01.dart
@@ -3,48 +3,66 @@
 // BSD-style license that can be found in the LICENSE file.
 
 /// @assertion void createSync(
-///  String target, {
-///  bool recursive: false
-///  })
+///   String target,
+///   {bool recursive = false}
+/// )
 ///  Synchronously create the link. Calling createSync on an existing link will
 ///  throw an exception.
 ///
-///  If recursive is false, the default, the link is created only if all
-///  directories in its path exist. If recursive is true, all non-existing path
-///  components are created. The directories in the path of target are not
-///  affected, unless they are also in path.
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. 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. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
 ///
-///  On other platforms, the posix symlink() call is used to make a symbolic link
-///  containing the string target. If target is a relative path, it will be
-///  interpreted relative to the directory containing the link.
-/// @description Checks that on non-Windows platforms only absolute links will be
-/// created, and relative paths to the target will be interpreted relative to the
-/// directory containing the link.
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to
+/// [Directory]
 /// @author sgrekhov@unipro.ru
+/// @issue 53689
 
 import "dart:io";
 import "../../../Utils/expect.dart";
 import "../file_utils.dart";
 
-main() async {
-  await inSandbox(_main);
+main() {
+  inSandbox(_main);
 }
 
-_main(Directory sandbox) async {
-  if (!Platform.isWindows) {
-    Directory dir = getTempDirectorySync(parent: sandbox);
-    String dirName = getTempDirectoryName();
-    Directory target = new Directory(dir.path +
-        Platform.pathSeparator + dirName);
-    target.createSync();
-    Link link = new Link(dir.path + Platform.pathSeparator +
-        getTempFileName(extension: "lnk"));
-    link.createSync(dirName);
-    Expect.equals(dirName, link.targetSync());
+_main(Directory sandbox) {
+  String dirName = getTempDirectoryName();
+  Directory target = Directory(sandbox.path + Platform.pathSeparator + dirName);
+  target.createSync();
+  Link link = Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(dirName);
+  Expect.equals(dirName, link.targetSync());
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  // Now create a directory and move the link into it. Its relative target
+  // should point to a not existing entity after it
+  Directory dir = getTempDirectorySync(parent: sandbox);
+  Link moved = link.renameSync(dir.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(dirName, moved.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(moved.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(moved.path));
   }
 }
diff --git a/LibTest/io/Link/createSync_A06_t02.dart b/LibTest/io/Link/createSync_A06_t02.dart
new file mode 100644
index 0000000000..f1288801cd
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t02.dart
@@ -0,0 +1,66 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to [File]
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String fileName = getTempFileName();
+  File target = new File(sandbox.path + Platform.pathSeparator + fileName);
+  target.createSync();
+  Link link = new Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(fileName);
+  Expect.equals(fileName, link.targetSync());
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  // Now create a directory and move the link into it. Its relative target
+  // should point to a not existing entity after it
+  Directory dir = getTempDirectorySync(parent: sandbox);
+  Link moved = link.renameSync(dir.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(fileName, moved.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(moved.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(moved.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A06_t03.dart b/LibTest/io/Link/createSync_A06_t03.dart
new file mode 100644
index 0000000000..fbf1154778
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t03.dart
@@ -0,0 +1,68 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to [Link]
+/// pointing to [Directory]
+/// @author sgrekhov22@gmail.com
+/// @issue 53689
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String linkName = getTempFileName();
+  Link target = new Link(sandbox.path + Platform.pathSeparator + linkName);
+  target.createSync(sandbox.path);
+  Link link = new Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(linkName);
+  Expect.equals(linkName, link.targetSync());
+  Expect.equals(
+      FileSystemEntityType.directory, FileSystemEntity.typeSync(link.path));
+  // Now create a directory and move the link into it. Its relative target
+  // should point to a not existing entity after it
+  Directory dir = getTempDirectorySync(parent: sandbox);
+  Link moved = link.renameSync(dir.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(linkName, moved.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(moved.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(moved.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A06_t04.dart b/LibTest/io/Link/createSync_A06_t04.dart
new file mode 100644
index 0000000000..ff2f939d78
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t04.dart
@@ -0,0 +1,68 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to [Link]
+/// pointing to [File]
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String linkName = getTempFileName();
+  File file = getTempFileSync(parent: sandbox);
+  Link target = Link(sandbox.path + Platform.pathSeparator + linkName);
+  target.createSync(file.path);
+  Link link = Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(linkName);
+  Expect.equals(linkName, link.targetSync());
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(link.path));
+  // Now create a directory and move the link into it. Its relative target
+  // should point to a not existing entity after it
+  Directory dir = getTempDirectorySync(parent: sandbox);
+  Link moved = link.renameSync(dir.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(linkName, moved.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(moved.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(moved.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A06_t05.dart b/LibTest/io/Link/createSync_A06_t05.dart
new file mode 100644
index 0000000000..f7f11a26b0
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t05.dart
@@ -0,0 +1,70 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to [Link]
+/// pointing to a not existing entity
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String notExisting = getTempFileName();
+  String target = getTempFileName(extension: "lnk");
+  getTempLinkSync(parent: sandbox, target: notExisting, name: target);
+  Link link = Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(target);
+  Expect.equals(target, link.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  // Now create a directory and into it the file with the name as link's
+  // target. Then move the link into the directory. Its relative target should
+  // point to that file after it
+  Directory dir = getTempDirectorySync(parent: sandbox);
+  File file = File(dir.path + Platform.pathSeparator + target);
+  file.createSync();
+  Link moved = link.renameSync(dir.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(target, moved.targetSync());
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(moved.path));
+}
diff --git a/LibTest/io/Link/createSync_A06_t06.dart b/LibTest/io/Link/createSync_A06_t06.dart
new file mode 100644
index 0000000000..a09a7f636c
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t06.dart
@@ -0,0 +1,77 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to [Link]
+/// pointing to a not existing entity
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String notExisting = getTempFileName();
+  String target = getTempFileName(extension: "lnk");
+  Link targetLink =
+      getTempLinkSync(parent: sandbox, target: notExisting, name: target);
+  Link link = Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(target);
+  Expect.equals(target, link.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  // Now create a directory and into it another directory with the name as
+  // link's target. Then move the link into the first directory. Its relative
+  // target should point to the second directory after it (except Windows)
+  Directory dir1 = getTempDirectorySync(parent: sandbox);
+  Directory dir2 = Directory(dir1.path + Platform.pathSeparator + target);
+  dir2.createSync();
+  Link moved =
+      link.renameSync(dir1.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(target, moved.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(moved.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.directory, FileSystemEntity.typeSync(moved.path));
+  }
+}
diff --git a/LibTest/io/Link/createSync_A06_t07.dart b/LibTest/io/Link/createSync_A06_t07.dart
new file mode 100644
index 0000000000..a68db79e1c
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t07.dart
@@ -0,0 +1,68 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path to a not
+/// existing entity
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String target = getTempFileName();
+  Link link = Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(target);
+  Expect.equals(target, link.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  // Now create a directory and into it the file with the name as link's
+  // target. Then move the link into the directory. Its relative target should
+  // point to that file after it
+  Directory dir = getTempDirectorySync(parent: sandbox);
+  File file = File(dir.path + Platform.pathSeparator + target);
+  file.createSync();
+  Link moved = link.renameSync(dir.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(target, moved.targetSync());
+  Expect.equals(
+      FileSystemEntityType.file, FileSystemEntity.typeSync(moved.path));
+}
diff --git a/LibTest/io/Link/createSync_A06_t08.dart b/LibTest/io/Link/createSync_A06_t08.dart
new file mode 100644
index 0000000000..af521a7d06
--- /dev/null
+++ b/LibTest/io/Link/createSync_A06_t08.dart
@@ -0,0 +1,74 @@
+// Copyright (c) 2023, 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.
+
+/// @assertion void createSync(
+///   String target,
+///   {bool recursive = false}
+/// )
+///  Synchronously create the link. Calling createSync on an existing link will
+///  throw an exception.
+///
+/// If recursive is false, the default, the link is created only if all
+/// directories in its path exist. If recursive is true, all non-existing parent
+/// paths are created first. The directories in the path of target are not
+/// affected, unless they are also in path.
+///
+/// On the Windows platform, this call will create a true symbolic link instead
+/// of a junction. The link represents a file or directory and does not change
+/// its type after creation. If [target] exists then the type of the link will
+/// match the type [target], otherwise a file symlink is created.
+///
+/// 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, it will be
+/// interpreted relative to the directory containing the link.
+///
+/// @description Checks that relative paths to the target will be interpreted
+/// relative to the directory containing the link. Test relative path a not
+/// existing entity
+/// @author sgrekhov22@gmail.com
+
+import "dart:io";
+import "../../../Utils/expect.dart";
+import "../file_utils.dart";
+
+main() {
+  inSandbox(_main);
+}
+
+_main(Directory sandbox) {
+  String target = "target";
+  Link link = Link(sandbox.path +
+      Platform.pathSeparator +
+      getTempFileName(extension: "lnk"));
+  link.createSync(target);
+  Expect.equals(target, link.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(link.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.notFound, FileSystemEntity.typeSync(link.path));
+  }
+  // Now create a directory and into it another directory with the name as
+  // link's target. Then move the link into the first directory. Its relative
+  // target should point to the second directory after it
+  Directory dir1 = getTempDirectorySync(parent: sandbox);
+  Directory dir2 = Directory(dir1.path + Platform.pathSeparator + target);
+  dir2.createSync();
+  Link moved =
+      link.renameSync(dir1.path + Platform.pathSeparator + "moved.lnk");
+  Expect.equals(target, moved.targetSync());
+  if (Platform.isWindows) {
+    Expect.equals(
+        FileSystemEntityType.link, FileSystemEntity.typeSync(moved.path));
+  } else {
+    Expect.equals(
+        FileSystemEntityType.directory, FileSystemEntity.typeSync(moved.path));
+  }
+}
diff --git a/LibTest/io/Link/create_A04_t05.dart b/LibTest/io/Link/create_A04_t05.dart
index 6101eadd4f..f08a7ad756 100644
--- a/LibTest/io/Link/create_A04_t05.dart
+++ b/LibTest/io/Link/create_A04_t05.dart
@@ -57,6 +57,10 @@ _main(Directory sandbox) async {
     if (Platform.isWindows) {
       Expect.equals(
           FileSystemEntityType.link, FileSystemEntity.typeSync(created.path));
+      File file = File(created.targetSync());
+      file.createSync();
+      Expect.equals(
+          FileSystemEntityType.file, FileSystemEntity.typeSync(created.path));
     } else {
       Expect.equals(FileSystemEntityType.notFound,
           FileSystemEntity.typeSync(created.path));
diff --git a/LibTest/io/Link/create_A04_t06.dart b/LibTest/io/Link/create_A04_t06.dart
index 1887a8f18c..563328df6b 100644
--- a/LibTest/io/Link/create_A04_t06.dart
+++ b/LibTest/io/Link/create_A04_t06.dart
@@ -54,6 +54,10 @@ _main(Directory sandbox) async {
     if (Platform.isWindows) {
       Expect.equals(
           FileSystemEntityType.link, FileSystemEntity.typeSync(created.path));
+      File file = File(created.targetSync());
+      file.createSync();
+      Expect.equals(
+          FileSystemEntityType.file, FileSystemEntity.typeSync(created.path));
     } else {
       Expect.equals(FileSystemEntityType.notFound,
           FileSystemEntity.typeSync(created.path));
diff --git a/LibTest/io/Link/create_A06_t05.dart b/LibTest/io/Link/create_A06_t05.dart
index a07e6ea24e..8efa79963b 100644
--- a/LibTest/io/Link/create_A06_t05.dart
+++ b/LibTest/io/Link/create_A06_t05.dart
@@ -51,8 +51,7 @@ main() async {
 _main(Directory sandbox) async {
   String notExisting = getTempFileName();
   String target = getTempFileName(extension: "lnk");
-  Link targetLink =
-      getTempLinkSync(parent: sandbox, target: notExisting, name: target);
+  getTempLinkSync(parent: sandbox, target: notExisting, name: target);
   Link link = Link(sandbox.path +
       Platform.pathSeparator +
       getTempFileName(extension: "lnk"));