diff --git a/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/JGitTestUtil.java b/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/JGitTestUtil.java
index 136c64726..521593ea8 100644
--- a/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/JGitTestUtil.java
+++ b/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/JGitTestUtil.java
@@ -55,6 +55,7 @@
 import java.lang.reflect.Method;
 import java.net.URISyntaxException;
 import java.net.URL;
+import java.nio.file.Path;
 
 import org.eclipse.jgit.lib.Repository;
 import org.eclipse.jgit.util.FileUtils;
@@ -240,4 +241,10 @@ public static void deleteTrashFile(final Repository db,
 		FileUtils.delete(path);
 	}
 
+	public static Path writeLink(Repository db, String link,
+			String target) throws Exception {
+		return FileUtils.createSymLink(new File(db.getWorkTree(), link),
+				target);
+	}
+
 }
diff --git a/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/RepositoryTestCase.java b/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/RepositoryTestCase.java
index ac4539a84..28c61778c 100644
--- a/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/RepositoryTestCase.java
+++ b/org.eclipse.jgit.junit/src/org/eclipse/jgit/junit/RepositoryTestCase.java
@@ -55,6 +55,7 @@
 import java.io.IOException;
 import java.io.InputStreamReader;
 import java.io.Reader;
+import java.nio.file.Path;
 import java.util.Map;
 
 import org.eclipse.jgit.api.Git;
@@ -107,6 +108,11 @@ protected File writeTrashFile(final String name, final String data)
 		return JGitTestUtil.writeTrashFile(db, name, data);
 	}
 
+	protected Path writeLink(final String link, final String target)
+			throws Exception {
+		return JGitTestUtil.writeLink(db, link, target);
+	}
+
 	protected File writeTrashFile(final String subdir, final String name,
 			final String data)
 			throws IOException {
diff --git a/org.eclipse.jgit.test/tst/org/eclipse/jgit/lib/DirCacheCheckoutTest.java b/org.eclipse.jgit.test/tst/org/eclipse/jgit/lib/DirCacheCheckoutTest.java
index a8a54a8df..6d62528f8 100644
--- a/org.eclipse.jgit.test/tst/org/eclipse/jgit/lib/DirCacheCheckoutTest.java
+++ b/org.eclipse.jgit.test/tst/org/eclipse/jgit/lib/DirCacheCheckoutTest.java
@@ -923,6 +923,299 @@ public void testCheckoutOutChanges() throws IOException {
 		}
 	}
 
+	@Test
+	public void testCheckoutChangeLinkToEmptyDir() throws Exception {
+		String fname = "was_file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+
+		// Add a link to file
+		String linkName = "link";
+		File link = writeLink(linkName, fname).toFile();
+		git.add().addFilepattern(linkName).call();
+		git.commit().setMessage("Added file and link").call();
+
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		// replace link with empty directory
+		FileUtils.delete(link);
+		FileUtils.mkdir(link);
+		assertTrue("Link must be a directory now", link.isDirectory());
+
+		// modify file
+		writeTrashFile(fname, "b");
+		assertWorkDir(mkmap(fname, "b", linkName, "/"));
+
+		// revert both paths to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD)
+				.addPath(fname).addPath(linkName).call();
+
+		assertWorkDir(mkmap(fname, "a", linkName, "a"));
+
+		Status st = git.status().call();
+		assertTrue(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeLinkToEmptyDirs() throws Exception {
+		String fname = "was_file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+
+		// Add a link to file
+		String linkName = "link";
+		File link = writeLink(linkName, fname).toFile();
+		git.add().addFilepattern(linkName).call();
+		git.commit().setMessage("Added file and link").call();
+
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		// replace link with directory containing only directories, no files
+		FileUtils.delete(link);
+		FileUtils.mkdirs(new File(link, "dummyDir"));
+		assertTrue("Link must be a directory now", link.isDirectory());
+
+		assertFalse("Must not delete non empty directory", link.delete());
+
+		// modify file
+		writeTrashFile(fname, "b");
+		assertWorkDir(mkmap(fname, "b", linkName + "/dummyDir", "/"));
+
+		// revert both paths to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD)
+				.addPath(fname).addPath(linkName).call();
+
+		assertWorkDir(mkmap(fname, "a", linkName, "a"));
+
+		Status st = git.status().call();
+		assertTrue(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeLinkToNonEmptyDirs() throws Exception {
+		String fname = "file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+
+		// Add a link to file
+		String linkName = "link";
+		File link = writeLink(linkName, fname).toFile();
+		git.add().addFilepattern(linkName).call();
+		git.commit().setMessage("Added file and link").call();
+
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		// replace link with directory containing only directories, no files
+		FileUtils.delete(link);
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(linkName + "/dir1", "file1", "c");
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(linkName + "/dir2", "file2", "d");
+
+		assertTrue("File must be a directory now", link.isDirectory());
+		assertFalse("Must not delete non empty directory", link.delete());
+
+		// 2 extra files are created
+		assertWorkDir(mkmap(fname, "a", linkName + "/dir1/file1", "c",
+				linkName + "/dir2/file2", "d"));
+
+		// revert path to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD).addPath(linkName).call();
+
+		// expect only the one added to the index
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		Status st = git.status().call();
+		assertTrue(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeLinkToNonEmptyDirsAndNewIndexEntry()
+			throws Exception {
+		String fname = "file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+
+		// Add a link to file
+		String linkName = "link";
+		File link = writeLink(linkName, fname).toFile();
+		git.add().addFilepattern(linkName).call();
+		git.commit().setMessage("Added file and link").call();
+
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		// replace link with directory containing only directories, no files
+		FileUtils.delete(link);
+
+		// create and add a file in the new directory to the index
+		writeTrashFile(linkName + "/dir1", "file1", "c");
+		git.add().addFilepattern(linkName + "/dir1/file1").call();
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(linkName + "/dir2", "file2", "d");
+
+		assertTrue("File must be a directory now", link.isDirectory());
+		assertFalse("Must not delete non empty directory", link.delete());
+
+		// 2 extra files are created
+		assertWorkDir(mkmap(fname, "a", linkName + "/dir1/file1", "c",
+				linkName + "/dir2/file2", "d"));
+
+		// revert path to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD).addPath(linkName).call();
+
+		// original file and link
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		Status st = git.status().call();
+		assertFalse(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeFileToEmptyDir() throws Exception {
+		String fname = "was_file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		File file = writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+		git.commit().setMessage("Added file").call();
+
+		// replace file with empty directory
+		FileUtils.delete(file);
+		FileUtils.mkdir(file);
+		assertTrue("File must be a directory now", file.isDirectory());
+
+		assertWorkDir(mkmap(fname, "/"));
+
+		// revert path to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD).addPath(fname).call();
+
+		assertWorkDir(mkmap(fname, "a"));
+
+		Status st = git.status().call();
+		assertTrue(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeFileToEmptyDirs() throws Exception {
+		String fname = "was_file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		File file = writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+		git.commit().setMessage("Added file").call();
+
+		// replace file with directory containing only directories, no files
+		FileUtils.delete(file);
+		FileUtils.mkdirs(new File(file, "dummyDir"));
+		assertTrue("File must be a directory now", file.isDirectory());
+		assertFalse("Must not delete non empty directory", file.delete());
+
+		assertWorkDir(mkmap(fname + "/dummyDir", "/"));
+
+		// revert path to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD).addPath(fname).call();
+
+		assertWorkDir(mkmap(fname, "a"));
+
+		Status st = git.status().call();
+		assertTrue(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeFileToNonEmptyDirs() throws Exception {
+		String fname = "was_file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		File file = writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+		git.commit().setMessage("Added file").call();
+
+		assertWorkDir(mkmap(fname, "a"));
+
+		// replace file with directory containing only directories, no files
+		FileUtils.delete(file);
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(fname + "/dir1", "file1", "c");
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(fname + "/dir2", "file2", "d");
+
+		assertTrue("File must be a directory now", file.isDirectory());
+		assertFalse("Must not delete non empty directory", file.delete());
+
+		// 2 extra files are created
+		assertWorkDir(
+				mkmap(fname + "/dir1/file1", "c", fname + "/dir2/file2", "d"));
+
+		// revert path to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD).addPath(fname).call();
+
+		// expect only the one added to the index
+		assertWorkDir(mkmap(fname, "a"));
+
+		Status st = git.status().call();
+		assertTrue(st.isClean());
+	}
+
+	@Test
+	public void testCheckoutChangeFileToNonEmptyDirsAndNewIndexEntry()
+			throws Exception {
+		String fname = "was_file";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		File file = writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+		git.commit().setMessage("Added file").call();
+
+		assertWorkDir(mkmap(fname, "a"));
+
+		// replace file with directory containing only directories, no files
+		FileUtils.delete(file);
+
+		// create and add a file in the new directory to the index
+		writeTrashFile(fname + "/dir", "file1", "c");
+		git.add().addFilepattern(fname + "/dir/file1").call();
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(fname + "/dir", "file2", "d");
+
+		assertTrue("File must be a directory now", file.isDirectory());
+		assertFalse("Must not delete non empty directory", file.delete());
+
+		// 2 extra files are created
+		assertWorkDir(
+				mkmap(fname + "/dir/file1", "c", fname + "/dir/file2", "d"));
+
+		// revert path to HEAD state
+		git.checkout().setStartPoint(Constants.HEAD).addPath(fname).call();
+		assertWorkDir(mkmap(fname, "a"));
+
+		Status st = git.status().call();
+		assertFalse(st.isClean());
+		assertEquals(1, st.getAdded().size());
+		assertTrue(st.getAdded().contains(fname + "/dir/file1"));
+	}
+
 	@Test
 	public void testCheckoutOutChangesAutoCRLFfalse() throws IOException {
 		setupCase(mk("foo"), mkmap("foo/bar", "foo\nbar"), mk("foo"));
@@ -1023,6 +1316,102 @@ public void testOverwriteUntrackedIgnoredFile() throws IOException,
 		assertTrue(git.status().call().isClean());
 	}
 
+	@Test
+	public void testOverwriteUntrackedFileModeChange()
+			throws IOException, GitAPIException {
+		String fname = "file.txt";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		File file = writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+		git.commit().setMessage("create file").call();
+		assertWorkDir(mkmap(fname, "a"));
+
+		// Create branch
+		git.branchCreate().setName("side").call();
+
+		// Switch branches
+		git.checkout().setName("side").call();
+
+		// replace file with directory containing files
+		FileUtils.delete(file);
+
+		// create and add a file in the new directory to the index
+		writeTrashFile(fname + "/dir1", "file1", "c");
+		git.add().addFilepattern(fname + "/dir1/file1").call();
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(fname + "/dir2", "file2", "d");
+
+		assertTrue("File must be a directory now", file.isDirectory());
+		assertFalse("Must not delete non empty directory", file.delete());
+
+		// 2 extra files are created
+		assertWorkDir(
+				mkmap(fname + "/dir1/file1", "c", fname + "/dir2/file2", "d"));
+
+		try {
+			git.checkout().setName("master").call();
+			fail("did not throw exception");
+		} catch (Exception e) {
+			// 2 extra files are still there
+			assertWorkDir(mkmap(fname + "/dir1/file1", "c",
+					fname + "/dir2/file2", "d"));
+		}
+	}
+
+	@Test
+	public void testOverwriteUntrackedLinkModeChange()
+			throws Exception {
+		String fname = "file.txt";
+		Git git = Git.wrap(db);
+
+		// Add a file
+		writeTrashFile(fname, "a");
+		git.add().addFilepattern(fname).call();
+
+		// Add a link to file
+		String linkName = "link";
+		File link = writeLink(linkName, fname).toFile();
+		git.add().addFilepattern(linkName).call();
+		git.commit().setMessage("Added file and link").call();
+
+		assertWorkDir(mkmap(linkName, "a", fname, "a"));
+
+		// Create branch
+		git.branchCreate().setName("side").call();
+
+		// Switch branches
+		git.checkout().setName("side").call();
+
+		// replace link with directory containing files
+		FileUtils.delete(link);
+
+		// create and add a file in the new directory to the index
+		writeTrashFile(linkName + "/dir1", "file1", "c");
+		git.add().addFilepattern(linkName + "/dir1/file1").call();
+
+		// create but do not add a file in the new directory to the index
+		writeTrashFile(linkName + "/dir2", "file2", "d");
+
+		assertTrue("Link must be a directory now", link.isDirectory());
+		assertFalse("Must not delete non empty directory", link.delete());
+
+		// 2 extra files are created
+		assertWorkDir(mkmap(fname, "a", linkName + "/dir1/file1", "c",
+				linkName + "/dir2/file2", "d"));
+
+		try {
+			git.checkout().setName("master").call();
+			fail("did not throw exception");
+		} catch (Exception e) {
+			// 2 extra files are still there
+			assertWorkDir(mkmap(fname, "a", linkName + "/dir1/file1", "c",
+					linkName + "/dir2/file2", "d"));
+		}
+	}
+
 	@Test
 	public void testFileModeChangeWithNoContentChangeUpdate() throws Exception {
 		if (!FS.DETECTED.supportsExecute())
@@ -1219,7 +1608,8 @@ public void testFileModeChangeAndContentChangeNoConflict() throws Exception {
 		assertNotNull(git.checkout().setName(Constants.MASTER).call());
 	}
 
-	public void assertWorkDir(HashMap<String, String> i) throws CorruptObjectException,
+	public void assertWorkDir(Map<String, String> i)
+			throws CorruptObjectException,
 			IOException {
 		TreeWalk walk = new TreeWalk(db);
 		walk.setRecursive(false);
diff --git a/org.eclipse.jgit/.settings/.api_filters b/org.eclipse.jgit/.settings/.api_filters
index a1e79e2d2..f34226c42 100644
--- a/org.eclipse.jgit/.settings/.api_filters
+++ b/org.eclipse.jgit/.settings/.api_filters
@@ -21,4 +21,12 @@
             </message_arguments>
         </filter>
     </resource>
+    <resource path="src/org/eclipse/jgit/util/FileUtils.java" type="org.eclipse.jgit.util.FileUtils">
+        <filter id="338792546">
+            <message_arguments>
+                <message_argument value="org.eclipse.jgit.util.FileUtils"/>
+                <message_argument value="createSymLink(File, String)"/>
+            </message_arguments>
+        </filter>
+    </resource>
 </component>
diff --git a/org.eclipse.jgit/src/org/eclipse/jgit/api/CheckoutCommand.java b/org.eclipse.jgit/src/org/eclipse/jgit/api/CheckoutCommand.java
index 8d8aada62..8d85bfcb1 100644
--- a/org.eclipse.jgit/src/org/eclipse/jgit/api/CheckoutCommand.java
+++ b/org.eclipse.jgit/src/org/eclipse/jgit/api/CheckoutCommand.java
@@ -457,7 +457,7 @@ public void apply(DirCacheEntry ent) {
 
 	private void checkoutPath(DirCacheEntry entry, ObjectReader reader) {
 		try {
-			DirCacheCheckout.checkoutEntry(repo, entry, reader);
+			DirCacheCheckout.checkoutEntry(repo, entry, reader, true);
 		} catch (IOException e) {
 			throw new JGitInternalException(MessageFormat.format(
 					JGitText.get().checkoutConflictWithFile,
diff --git a/org.eclipse.jgit/src/org/eclipse/jgit/api/StashApplyCommand.java b/org.eclipse.jgit/src/org/eclipse/jgit/api/StashApplyCommand.java
index 6de25a052..8ef550871 100644
--- a/org.eclipse.jgit/src/org/eclipse/jgit/api/StashApplyCommand.java
+++ b/org.eclipse.jgit/src/org/eclipse/jgit/api/StashApplyCommand.java
@@ -357,7 +357,7 @@ private void resetUntracked(RevTree tree) throws CheckoutConflictException,
 
 	private void checkoutPath(DirCacheEntry entry, ObjectReader reader) {
 		try {
-			DirCacheCheckout.checkoutEntry(repo, entry, reader);
+			DirCacheCheckout.checkoutEntry(repo, entry, reader, true);
 		} catch (IOException e) {
 			throw new JGitInternalException(MessageFormat.format(
 					JGitText.get().checkoutConflictWithFile,
diff --git a/org.eclipse.jgit/src/org/eclipse/jgit/dircache/DirCacheCheckout.java b/org.eclipse.jgit/src/org/eclipse/jgit/dircache/DirCacheCheckout.java
index 00252547d..0036ab508 100644
--- a/org.eclipse.jgit/src/org/eclipse/jgit/dircache/DirCacheCheckout.java
+++ b/org.eclipse.jgit/src/org/eclipse/jgit/dircache/DirCacheCheckout.java
@@ -447,7 +447,7 @@ private boolean doCheckout() throws CorruptObjectException, IOException,
 			for (String path : updated.keySet()) {
 				DirCacheEntry entry = dc.getEntry(path);
 				if (!FileMode.GITLINK.equals(entry.getRawMode()))
-					checkoutEntry(repo, entry, objectReader);
+					checkoutEntry(repo, entry, objectReader, false);
 			}
 
 			// commit the index builder - a new index is persisted
@@ -1127,6 +1127,13 @@ private boolean isModifiedSubtree_IndexTree(String path, ObjectId tree)
 	 * final filename.
 	 *
 	 * <p>
+	 * <b>Note:</b> if the entry path on local file system exists as a non-empty
+	 * directory, and the target entry type is a link or file, the checkout will
+	 * fail with {@link IOException} since existing non-empty directory cannot
+	 * be renamed to file or link without deleting it recursively.
+	 * </p>
+	 *
+	 * <p>
 	 * TODO: this method works directly on File IO, we may need another
 	 * abstraction (like WorkingTreeIterator). This way we could tell e.g.
 	 * Eclipse that Files in the workspace got changed
@@ -1143,6 +1150,42 @@ private boolean isModifiedSubtree_IndexTree(String path, ObjectId tree)
 	 */
 	public static void checkoutEntry(Repository repo, DirCacheEntry entry,
 			ObjectReader or) throws IOException {
+		checkoutEntry(repo, entry, or, false);
+	}
+
+	/**
+	 * Updates the file in the working tree with content and mode from an entry
+	 * in the index. The new content is first written to a new temporary file in
+	 * the same directory as the real file. Then that new file is renamed to the
+	 * final filename.
+	 *
+	 * <p>
+	 * <b>Note:</b> if the entry path on local file system exists as a file, it
+	 * will be deleted and if it exists as a directory, it will be deleted
+	 * recursively, independently if has any content.
+	 * </p>
+	 *
+	 * <p>
+	 * TODO: this method works directly on File IO, we may need another
+	 * abstraction (like WorkingTreeIterator). This way we could tell e.g.
+	 * Eclipse that Files in the workspace got changed
+	 * </p>
+	 *
+	 * @param repo
+	 *            repository managing the destination work tree.
+	 * @param entry
+	 *            the entry containing new mode and content
+	 * @param or
+	 *            object reader to use for checkout
+	 * @param deleteRecursive
+	 *            true to recursively delete final path if it exists on the file
+	 *            system
+	 *
+	 * @throws IOException
+	 * @since 4.2
+	 */
+	public static void checkoutEntry(Repository repo, DirCacheEntry entry,
+			ObjectReader or, boolean deleteRecursive) throws IOException {
 		ObjectLoader ol = or.open(entry.getObjectId());
 		File f = new File(repo.getWorkTree(), entry.getPathString());
 		File parentDir = f.getParentFile();
@@ -1153,6 +1196,9 @@ public static void checkoutEntry(Repository repo, DirCacheEntry entry,
 				&& opt.getSymLinks() == SymLinks.TRUE) {
 			byte[] bytes = ol.getBytes();
 			String target = RawParseUtils.decode(bytes);
+			if (deleteRecursive && f.isDirectory()) {
+				FileUtils.delete(f, FileUtils.RECURSIVE);
+			}
 			fs.createSymLink(f, target);
 			entry.setLength(bytes.length);
 			entry.setLastModified(fs.lastModified(f));
@@ -1183,11 +1229,18 @@ public static void checkoutEntry(Repository repo, DirCacheEntry entry,
 			}
 		}
 		try {
+			if (deleteRecursive && f.isDirectory()) {
+				FileUtils.delete(f, FileUtils.RECURSIVE);
+			}
 			FileUtils.rename(tmpFile, f);
 		} catch (IOException e) {
 			throw new IOException(MessageFormat.format(
 					JGitText.get().renameFileFailed, tmpFile.getPath(),
 					f.getPath()));
+		} finally {
+			if (tmpFile.exists()) {
+				FileUtils.delete(tmpFile);
+			}
 		}
 		entry.setLastModified(f.lastModified());
 	}
diff --git a/org.eclipse.jgit/src/org/eclipse/jgit/util/FileUtils.java b/org.eclipse.jgit/src/org/eclipse/jgit/util/FileUtils.java
index 548d239c8..720fdedef 100644
--- a/org.eclipse.jgit/src/org/eclipse/jgit/util/FileUtils.java
+++ b/org.eclipse.jgit/src/org/eclipse/jgit/util/FileUtils.java
@@ -399,20 +399,25 @@ public static void createNewFile(File f) throws IOException {
 	 *
 	 * @param path
 	 * @param target
+	 * @return path to the created link
 	 * @throws IOException
-	 * @since 3.0
+	 * @since 4.2
 	 */
-	public static void createSymLink(File path, String target)
+	public static Path createSymLink(File path, String target)
 			throws IOException {
 		Path nioPath = path.toPath();
 		if (Files.exists(nioPath, LinkOption.NOFOLLOW_LINKS)) {
-			Files.delete(nioPath);
+			if (Files.isRegularFile(nioPath)) {
+				delete(path);
+			} else {
+				delete(path, EMPTY_DIRECTORIES_ONLY | RECURSIVE);
+			}
 		}
 		if (SystemReader.getInstance().isWindows()) {
 			target = target.replace('/', '\\');
 		}
 		Path nioTarget = new File(target).toPath();
-		Files.createSymbolicLink(nioPath, nioTarget);
+		return Files.createSymbolicLink(nioPath, nioTarget);
 	}
 
 	/**