diff --git a/Flow.Launcher.Core/Plugin/PluginConfig.cs b/Flow.Launcher.Core/Plugin/PluginConfig.cs
index 4bf12faff..db6813deb 100644
--- a/Flow.Launcher.Core/Plugin/PluginConfig.cs
+++ b/Flow.Launcher.Core/Plugin/PluginConfig.cs
@@ -6,6 +6,7 @@ using Flow.Launcher.Infrastructure;
 using Flow.Launcher.Plugin;
 using System.Text.Json;
 using Flow.Launcher.Infrastructure.UserSettings;
+using Flow.Launcher.Plugin.SharedCommands;
 
 namespace Flow.Launcher.Core.Plugin
 {
@@ -30,7 +31,18 @@ namespace Flow.Launcher.Core.Plugin
                 {
                     try
                     {
-                        Directory.Delete(directory, true);
+                        var fullyDeleted = FilesFolders.TryDeleteDirectoryRobust(directory, maxRetries: 3, retryDelayMs: 200);
+                        if (!fullyDeleted)
+                        {
+                            PublicApi.Instance.LogWarn(ClassName, $"Directory <{directory}> was not fully deleted.");
+
+                            // Directory was not fully deleted, recreate the marker file so deletion will be retried on next startup
+                            var markerFilePath = Path.Combine(directory, DataLocation.PluginDeleteFile);
+                            if (!File.Exists(markerFilePath))
+                            {
+                                File.WriteAllText(markerFilePath, string.Empty);
+                            }
+                        }
                     }
                     catch (Exception e)
                     {
diff --git a/Flow.Launcher.Core/Plugin/PluginManager.cs b/Flow.Launcher.Core/Plugin/PluginManager.cs
index 54712942c..b808e2a7f 100644
--- a/Flow.Launcher.Core/Plugin/PluginManager.cs
+++ b/Flow.Launcher.Core/Plugin/PluginManager.cs
@@ -931,6 +931,18 @@ namespace Flow.Launcher.Core.Plugin
 
             FilesFolders.CopyAll(pluginFolderPath, newPluginPath, (s) => PublicApi.Instance.ShowMsgBox(s));
 
+            // Check if marker file exists and delete it
+            try
+            {
+                var markerFilePath = Path.Combine(newPluginPath, DataLocation.PluginDeleteFile);
+                if (File.Exists(markerFilePath))
+                    File.Delete(markerFilePath);
+            }
+            catch (Exception e)
+            {
+                PublicApi.Instance.LogException(ClassName, $"Failed to delete plugin marker file in {newPluginPath}", e);
+            }
+
             try
             {
                 if (Directory.Exists(tempFolderPluginPath))
diff --git a/Flow.Launcher.Plugin/SharedCommands/FilesFolders.cs b/Flow.Launcher.Plugin/SharedCommands/FilesFolders.cs
index 3af57f00d..cd1ddf983 100644
--- a/Flow.Launcher.Plugin/SharedCommands/FilesFolders.cs
+++ b/Flow.Launcher.Plugin/SharedCommands/FilesFolders.cs
@@ -130,6 +130,119 @@ namespace Flow.Launcher.Plugin.SharedCommands
             }
         }
 
+        /// <summary>
+        /// Attempts to delete a directory robustly with retry logic for locked files.
+        /// This method tries to delete files individually with retries, then removes empty directories.
+        /// Returns true if the directory was completely deleted, false if some files/folders remain.
+        /// </summary>
+        /// <param name="path">The directory path to delete</param>
+        /// <param name="maxRetries">Maximum number of retry attempts for locked files (default: 3)</param>
+        /// <param name="retryDelayMs">Delay in milliseconds between retries (default: 100ms)</param>
+        /// <returns>True if directory was fully deleted, false if some items remain</returns>
+        public static bool TryDeleteDirectoryRobust(string path, int maxRetries = 3, int retryDelayMs = 100)
+        {
+            if (!Directory.Exists(path))
+                return true;
+
+            bool fullyDeleted = true;
+
+            try
+            {
+                // First, try to delete all files in the directory tree
+                var files = Directory.GetFiles(path, "*", SearchOption.AllDirectories);
+                foreach (var file in files)
+                {
+                    bool fileDeleted = false;
+                    for (int attempt = 0; attempt <= maxRetries; attempt++)
+                    {
+                        try
+                        {
+                            // Remove read-only attribute if present
+                            var fileInfo = new FileInfo(file);
+                            if (fileInfo.Exists && fileInfo.IsReadOnly)
+                            {
+                                fileInfo.IsReadOnly = false;
+                            }
+
+                            File.Delete(file);
+                            fileDeleted = true;
+                            break;
+                        }
+                        catch (UnauthorizedAccessException)
+                        {
+                            // File is in use or access denied, wait and retry
+                            if (attempt < maxRetries)
+                            {
+                                System.Threading.Thread.Sleep(retryDelayMs);
+                            }
+                        }
+                        catch (IOException)
+                        {
+                            // File is in use, wait and retry
+                            if (attempt < maxRetries)
+                            {
+                                System.Threading.Thread.Sleep(retryDelayMs);
+                            }
+                        }
+                        catch
+                        {
+                            // Other exceptions, don't retry
+                            break;
+                        }
+                    }
+
+                    if (!fileDeleted)
+                    {
+                        fullyDeleted = false;
+                    }
+                }
+
+                // Then, try to delete all empty directories (from deepest to shallowest)
+                var directories = Directory.GetDirectories(path, "*", SearchOption.AllDirectories)
+                    .OrderByDescending(d => d.Length) // Delete deeper directories first
+                    .ToArray();
+
+                foreach (var directory in directories)
+                {
+                    try
+                    {
+                        if (Directory.Exists(directory) && !Directory.EnumerateFileSystemEntries(directory).Any())
+                        {
+                            Directory.Delete(directory, false);
+                        }
+                    }
+                    catch
+                    {
+                        // If we can't delete an empty directory, mark as not fully deleted
+                        fullyDeleted = false;
+                    }
+                }
+
+                // Finally, try to delete the root directory itself
+                try
+                {
+                    if (Directory.Exists(path) && !Directory.EnumerateFileSystemEntries(path).Any())
+                    {
+                        Directory.Delete(path, false);
+                    }
+                    else if (Directory.Exists(path))
+                    {
+                        fullyDeleted = false;
+                    }
+                }
+                catch
+                {
+                    fullyDeleted = false;
+                }
+            }
+            catch
+            {
+                fullyDeleted = false;
+            }
+
+            return fullyDeleted;
+        }
+
         /// <summary>
         /// Checks if a directory exists
         /// </summary>
diff --git a/Flow.Launcher.Test/FilesFoldersTest.cs b/Flow.Launcher.Test/FilesFoldersTest.cs
index 2621fc2da..a63b59c39 100644
--- a/Flow.Launcher.Test/FilesFoldersTest.cs
+++ b/Flow.Launcher.Test/FilesFoldersTest.cs
@@ -1,6 +1,7 @@
 using Flow.Launcher.Plugin.SharedCommands;
 using NUnit.Framework;
 using NUnit.Framework.Legacy;
+using System.IO;
 
 namespace Flow.Launcher.Test
 {
@@ -50,5 +51,89 @@ namespace Flow.Launcher.Test
         {
             ClassicAssert.AreEqual(expectedResult, FilesFolders.PathContains(parentPath, path, allowEqual: expectedResult));
         }
+
+        [Test]
+        public void TryDeleteDirectoryRobust_WhenDirectoryDoesNotExist_ReturnsTrue()
+        {
+            // Arrange
+            string nonExistentPath = Path.Combine(Path.GetTempPath(), Path.GetRandomFileName());
+
+            // Act
+            bool result = FilesFolders.TryDeleteDirectoryRobust(nonExistentPath);
+
+            // Assert
+            ClassicAssert.IsTrue(result);
+        }
+
+        [Test]
+        public void TryDeleteDirectoryRobust_WhenDirectoryIsEmpty_DeletesSuccessfully()
+        {
+            // Arrange
+            string tempDir = Path.Combine(Path.GetTempPath(), Path.GetRandomFileName());
+            Directory.CreateDirectory(tempDir);
+
+            // Act
+            bool result = FilesFolders.TryDeleteDirectoryRobust(tempDir);
+
+            // Assert
+            ClassicAssert.IsTrue(result);
+            ClassicAssert.IsFalse(Directory.Exists(tempDir));
+        }
+
+        [Test]
+        public void TryDeleteDirectoryRobust_WhenDirectoryHasFiles_DeletesSuccessfully()
+        {
+            // Arrange
+            string tempDir = Path.Combine(Path.GetTempPath(), Path.GetRandomFileName());
+            Directory.CreateDirectory(tempDir);
+            File.WriteAllText(Path.Combine(tempDir, "test.txt"), "test content");
+
+            // Act
+            bool result = FilesFolders.TryDeleteDirectoryRobust(tempDir);
+
+            // Assert
+            ClassicAssert.IsTrue(result);
+            ClassicAssert.IsFalse(Directory.Exists(tempDir));
+        }
+
+        [Test]
+        public void TryDeleteDirectoryRobust_WhenDirectoryHasNestedStructure_DeletesSuccessfully()
+        {
+            // Arrange
+            string tempDir = Path.Combine(Path.GetTempPath(), Path.GetRandomFileName());
+            Directory.CreateDirectory(tempDir);
+            string subDir1 = Path.Combine(tempDir, "SubDir1");
+            string subDir2 = Path.Combine(tempDir, "SubDir2");
+            Directory.CreateDirectory(subDir1);
+            Directory.CreateDirectory(subDir2);
+            File.WriteAllText(Path.Combine(subDir1, "file1.txt"), "content1");
+            File.WriteAllText(Path.Combine(subDir2, "file2.txt"), "content2");
+            File.WriteAllText(Path.Combine(tempDir, "root.txt"), "root content");
+
+            // Act
+            bool result = FilesFolders.TryDeleteDirectoryRobust(tempDir);
+
+            // Assert
+            ClassicAssert.IsTrue(result);
+            ClassicAssert.IsFalse(Directory.Exists(tempDir));
+        }
+
+        [Test]
+        public void TryDeleteDirectoryRobust_WhenFileIsReadOnly_RemovesAttributeAndDeletes()
+        {
+            // Arrange
+            string tempDir = Path.Combine(Path.GetTempPath(), Path.GetRandomFileName());
+            Directory.CreateDirectory(tempDir);
+            string filePath = Path.Combine(tempDir, "readonly.txt");
+            File.WriteAllText(filePath, "readonly content");
+            File.SetAttributes(filePath, FileAttributes.ReadOnly);
+
+            // Act
+            bool result = FilesFolders.TryDeleteDirectoryRobust(tempDir);
+
+            // Assert
+            ClassicAssert.IsTrue(result);
+            ClassicAssert.IsFalse(Directory.Exists(tempDir));
+        }
     }
 }