diff --git a/Plugins/Wox.Plugin.Program/Logger/ProgramLogger.cs b/Plugins/Wox.Plugin.Program/Logger/ProgramLogger.cs
index 587aba685..d9f92bca2 100644
--- a/Plugins/Wox.Plugin.Program/Logger/ProgramLogger.cs
+++ b/Plugins/Wox.Plugin.Program/Logger/ProgramLogger.cs
@@ -1,4 +1,4 @@
-using NLog;
+using NLog;
 using NLog.Config;
 using NLog.Targets;
 using System;
@@ -7,6 +7,7 @@
 using System.Runtime.CompilerServices;
 using System.Security;
 using Wox.Infrastructure;
+using Wox.Infrastructure.UserSettings;
 
 namespace Wox.Plugin.Program.Logger
 {
@@ -21,7 +22,7 @@ internal static class ProgramLogger
 
         static ProgramLogger()
         {
-            var path = Path.Combine(Constant.DataDirectory, DirectoryName, Constant.Version);
+            var path = Path.Combine(DataLocation.DataDirectory(), DirectoryName, Constant.Version);
             if (!Directory.Exists(path))
             {
                 Directory.CreateDirectory(path);
diff --git a/Wox.Core/Configuration/IPortable.cs b/Wox.Core/Configuration/IPortable.cs
new file mode 100644
index 000000000..b0af43672
--- /dev/null
+++ b/Wox.Core/Configuration/IPortable.cs
@@ -0,0 +1,16 @@
+
+namespace Wox.Core.Configuration
+{
+    public interface IPortable
+    {
+        void EnablePortableMode();
+        void DisablePortableMode();
+        void RemoveShortcuts();
+        void RemoveUninstallerEntry();
+        void CreateShortcuts();
+        void CreateUninstallerEntry();
+        void MoveUserDataFolder(string fromLocation, string toLocation);
+        void VerifyUserDataAfterMove(string fromLocation, string toLocation);
+        bool CanUpdatePortability();
+    }
+}
\ No newline at end of file
diff --git a/Wox.Core/Configuration/Portable.cs b/Wox.Core/Configuration/Portable.cs
new file mode 100644
index 000000000..ee916001b
--- /dev/null
+++ b/Wox.Core/Configuration/Portable.cs
@@ -0,0 +1,203 @@
+using Microsoft.Win32;
+using Squirrel;
+using System;
+using System.IO;
+using System.Reflection;
+using System.Windows;
+using Wox.Infrastructure;
+using Wox.Infrastructure.Logger;
+using Wox.Infrastructure.UserSettings;
+using Wox.Plugin.SharedCommands;
+
+namespace Wox.Core.Configuration
+{
+    public class Portable : IPortable
+    {
+        /// <summary>
+        /// As at Squirrel.Windows version 1.5.2, UpdateManager needs to be disposed after finish
+        /// </summary>
+        /// <returns></returns>
+        private UpdateManager NewUpdateManager()
+        {
+            return new UpdateManager(string.Empty, Constant.Wox, Constant.RootDirectory);
+        }
+
+        public void DisablePortableMode()
+        {
+            try
+            {
+                MoveUserDataFolder(DataLocation.PortableDataPath, DataLocation.RoamingDataPath);
+#if DEBUG
+                // Create shortcuts and uninstaller are not required in debug mode, 
+                // otherwise will repoint the path of the actual installed production version to the debug version
+#else
+                CreateShortcuts();
+                CreateUninstallerEntry();
+#endif
+                IndicateDeletion(DataLocation.PortableDataPath);
+
+                MessageBox.Show("Wox needs to restart to finish disabling portable mode, " +
+                    "after the restart your portable data profile will be deleted and roaming data profile kept");
+
+                UpdateManager.RestartApp();
+            }
+            catch (Exception e)
+            {
+#if !DEBUG
+                Log.Exception("Portable", "Error occured while disabling portable mode", e);
+#endif
+                throw;
+            }
+        }
+
+        public void EnablePortableMode()
+        {
+            try
+            {
+                MoveUserDataFolder(DataLocation.RoamingDataPath, DataLocation.PortableDataPath);
+#if DEBUG
+                // Remove shortcuts and uninstaller are not required in debug mode, 
+                // otherwise will delete the actual installed production version
+#else
+                RemoveShortcuts();
+                RemoveUninstallerEntry();
+#endif
+                IndicateDeletion(DataLocation.RoamingDataPath);
+
+                MessageBox.Show("Wox needs to restart to finish enabling portable mode, " +
+                    "after the restart your roaming data profile will be deleted and portable data profile kept");
+
+                UpdateManager.RestartApp();
+            }
+            catch (Exception e)
+            {
+#if !DEBUG
+                Log.Exception("Portable", "Error occured while enabling portable mode", e);
+#endif
+                throw;
+            }
+        }
+
+        public void RemoveShortcuts()
+        {
+            using (var portabilityUpdater = NewUpdateManager())
+            {
+                var exeName = Constant.Wox + ".exe";
+                portabilityUpdater.RemoveShortcutsForExecutable(exeName, ShortcutLocation.StartMenu);
+                portabilityUpdater.RemoveShortcutsForExecutable(exeName, ShortcutLocation.Desktop);
+                portabilityUpdater.RemoveShortcutsForExecutable(exeName, ShortcutLocation.Startup);
+            }
+        }
+
+        public void RemoveUninstallerEntry()
+        {
+            using (var portabilityUpdater = NewUpdateManager())
+            {
+                portabilityUpdater.RemoveUninstallerRegistryEntry();
+            }
+        }
+
+        public void MoveUserDataFolder(string fromLocation, string toLocation)
+        {
+            FilesFolders.Copy(fromLocation, toLocation);
+            VerifyUserDataAfterMove(fromLocation, toLocation);
+        }
+
+        public void VerifyUserDataAfterMove(string fromLocation, string toLocation)
+        {
+            FilesFolders.VerifyBothFolderFilesEqual(fromLocation, toLocation);
+        }
+
+        public void CreateShortcuts()
+        {
+            using (var portabilityUpdater = NewUpdateManager())
+            {
+                var exeName = Constant.Wox + ".exe";
+                portabilityUpdater.CreateShortcutsForExecutable(exeName, ShortcutLocation.StartMenu, false);
+                portabilityUpdater.CreateShortcutsForExecutable(exeName, ShortcutLocation.Desktop, false);
+                portabilityUpdater.CreateShortcutsForExecutable(exeName, ShortcutLocation.Startup, false);
+            }
+        }
+
+        public void CreateUninstallerEntry()
+        {
+            var uninstallRegSubKey = @"Software\Microsoft\Windows\CurrentVersion\Uninstall";
+            // NB: Sometimes the Uninstall key doesn't exist
+            using (var parentKey =
+                RegistryKey.OpenBaseKey(RegistryHive.CurrentUser, RegistryView.Default)
+                    .CreateSubKey("Uninstall", RegistryKeyPermissionCheck.ReadWriteSubTree)) {; }
+
+            var key = RegistryKey.OpenBaseKey(RegistryHive.CurrentUser, RegistryView.Default)
+                .CreateSubKey(uninstallRegSubKey + "\\" + Constant.Wox, RegistryKeyPermissionCheck.ReadWriteSubTree);
+            key.SetValue("DisplayIcon", Constant.ApplicationDirectory + "\\app.ico", RegistryValueKind.String);
+
+            using (var portabilityUpdater = NewUpdateManager())
+            {
+                portabilityUpdater.CreateUninstallerRegistryEntry();
+            }
+        }
+
+        internal void IndicateDeletion(string filePathTodelete)
+        {
+            using (StreamWriter sw = File.CreateText(filePathTodelete + "\\" + DataLocation.DeletionIndicatorFile)){}
+        }
+
+        ///<summary>
+        ///This method should be run at first before all methods during start up and should be run before determining which data location
+        ///will be used for Wox.
+        ///</summary>
+        public void PreStartCleanUpAfterPortabilityUpdate()
+        {
+            // Specify here so this method does not rely on other environment variables to initialise
+            var portableDataPath = Path.Combine(Directory.GetParent(Assembly.GetExecutingAssembly().Location.NonNull()).ToString(), "UserData");
+            var roamingDataPath = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.ApplicationData), "Wox");
+
+            bool DataLocationPortableDeleteRequired = false;
+            bool DataLocationRoamingDeleteRequired = false;
+
+            if ((roamingDataPath + "\\" + DataLocation.DeletionIndicatorFile).FileExits())
+                DataLocationRoamingDeleteRequired = true;
+
+            if ((portableDataPath + "\\" + DataLocation.DeletionIndicatorFile).FileExits())
+                DataLocationPortableDeleteRequired = true;
+
+            if (DataLocationRoamingDeleteRequired)
+            {
+                if(roamingDataPath.LocationExists())
+                    MessageBox.Show("Wox detected you restarted after enabling portable mode, " +
+                                    "your roaming data profile will now be deleted");
+
+                FilesFolders.RemoveFolderIfExists(roamingDataPath);
+
+                return;
+            }
+
+            if(DataLocationPortableDeleteRequired)
+            {
+                MessageBox.Show("Wox detected you restarted after disabling portable mode, " +
+                                    "your portable data profile will now be deleted");
+
+                FilesFolders.RemoveFolderIfExists(portableDataPath);
+
+                return;
+            }
+        }
+
+        public bool CanUpdatePortability()
+        {
+            var roamingLocationExists = DataLocation.RoamingDataPath.LocationExists();
+            var portableLocationExists = DataLocation.PortableDataPath.LocationExists();
+
+            if(roamingLocationExists && portableLocationExists)
+            {
+                MessageBox.Show(string.Format("Wox detected your user data exists both in {0} and " +
+                                    "{1}. {2}{2}Please delete {1} in order to proceed. No changes have occured.", 
+                                    DataLocation.PortableDataPath, DataLocation.RoamingDataPath, Environment.NewLine));
+
+                return false;
+            }
+
+            return true;
+        }
+    }
+}
diff --git a/Wox.Core/Plugin/PluginInstaller.cs b/Wox.Core/Plugin/PluginInstaller.cs
index ffdb0aa75..a867d2e10 100644
--- a/Wox.Core/Plugin/PluginInstaller.cs
+++ b/Wox.Core/Plugin/PluginInstaller.cs
@@ -34,7 +34,7 @@ internal static void Install(string path)
                     return;
                 }
 
-                string pluginFolerPath = Infrastructure.Constant.PluginsDirectory;
+                string pluginFolerPath = Infrastructure.UserSettings.DataLocation.PluginsDirectory;
 
                 string newPluginName = plugin.Name
                     .Replace("/", "_")
diff --git a/Wox.Core/Plugin/PluginManager.cs b/Wox.Core/Plugin/PluginManager.cs
index 3d1450648..aa1065dfb 100644
--- a/Wox.Core/Plugin/PluginManager.cs
+++ b/Wox.Core/Plugin/PluginManager.cs
@@ -32,20 +32,20 @@ public static class PluginManager
         // todo happlebao, this should not be public, the indicator function should be embeded 
         public static PluginsSettings Settings;
         private static List<PluginMetadata> _metadatas;
-        private static readonly string[] Directories = { Constant.PreinstalledDirectory, Constant.PluginsDirectory };
+        private static readonly string[] Directories = { Constant.PreinstalledDirectory, DataLocation.PluginsDirectory };
 
         private static void ValidateUserDirectory()
         {
-            if (!Directory.Exists(Constant.PluginsDirectory))
+            if (!Directory.Exists(DataLocation.PluginsDirectory))
             {
-                Directory.CreateDirectory(Constant.PluginsDirectory);
+                Directory.CreateDirectory(DataLocation.PluginsDirectory);
             }
         }
 
         private static void DeletePythonBinding()
         {
             const string binding = "wox.py";
-            var directory = Constant.PluginsDirectory;
+            var directory = DataLocation.PluginsDirectory;
             foreach (var subDirectory in Directory.GetDirectories(directory))
             {
                 var path = Path.Combine(subDirectory, binding);
diff --git a/Wox.Core/Resource/Theme.cs b/Wox.Core/Resource/Theme.cs
index fc5d55046..b011b4f49 100644
--- a/Wox.Core/Resource/Theme.cs
+++ b/Wox.Core/Resource/Theme.cs
@@ -23,7 +23,7 @@ public class Theme
         private const string Folder = "Themes";
         private const string Extension = ".xaml";
         private string DirectoryPath => Path.Combine(Constant.ProgramDirectory, Folder);
-        private string UserDirectoryPath => Path.Combine(Constant.DataDirectory, Folder);
+        private string UserDirectoryPath => Path.Combine(DataLocation.DataDirectory(), Folder);
 
         public Theme()
         {
diff --git a/Wox.Core/Updater.cs b/Wox.Core/Updater.cs
index 9262d78f4..6a04def9f 100644
--- a/Wox.Core/Updater.cs
+++ b/Wox.Core/Updater.cs
@@ -15,6 +15,7 @@
 using Wox.Infrastructure.Http;
 using Wox.Infrastructure.Logger;
 using System.IO;
+using Wox.Infrastructure.UserSettings;
 
 namespace Wox.Core
 {
@@ -80,13 +81,13 @@ public async Task UpdateApp(bool silentIfLatestVersion = true)
             
             await updateManager.ApplyReleases(newUpdateInfo);
 
-            if (Constant.IsPortableMode)
+            if (DataLocation.PortableDataLocationInUse())
             {
-                var targetDestination = updateManager.RootAppDirectory + $"\\app-{newReleaseVersion.ToString()}\\{Constant.PortableFolderName}";
-                FilesFolders.Copy(Constant.PortableDataPath, targetDestination);
-                if (!FilesFolders.VerifyBothFolderFilesEqual(Constant.PortableDataPath, targetDestination))
+                var targetDestination = updateManager.RootAppDirectory + $"\\app-{newReleaseVersion.ToString()}\\{DataLocation.PortableFolderName}";
+                FilesFolders.Copy(DataLocation.PortableDataPath, targetDestination);
+                if (!FilesFolders.VerifyBothFolderFilesEqual(DataLocation.PortableDataPath, targetDestination))
                     MessageBox.Show(string.Format("Wox was not able to move your user profile data to the new update version. Please manually" +
-                        "move your profile data folder from {0} to {1}", Constant.PortableDataPath, targetDestination));
+                        "move your profile data folder from {0} to {1}", DataLocation.PortableDataPath, targetDestination));
             }
             else
             {
diff --git a/Wox.Core/Wox.Core.csproj b/Wox.Core/Wox.Core.csproj
index 7307243e6..0c5e0c178 100644
--- a/Wox.Core/Wox.Core.csproj
+++ b/Wox.Core/Wox.Core.csproj
@@ -51,6 +51,8 @@
     <Compile Include="..\SolutionAssemblyInfo.cs">
       <Link>Properties\SolutionAssemblyInfo.cs</Link>
     </Compile>
+    <Compile Include="Configuration\IPortable.cs" />
+    <Compile Include="Configuration\Portable.cs" />
     <Compile Include="Plugin\ExecutablePlugin.cs" />
     <Compile Include="Plugin\PluginsLoader.cs" />
     <Compile Include="Resource\LocalizationConverter.cs" />
diff --git a/Wox.Infrastructure/Wox.cs b/Wox.Infrastructure/Constant.cs
similarity index 60%
rename from Wox.Infrastructure/Wox.cs
rename to Wox.Infrastructure/Constant.cs
index 16629e4fb..78a08ca69 100644
--- a/Wox.Infrastructure/Wox.cs
+++ b/Wox.Infrastructure/Constant.cs
@@ -1,4 +1,3 @@
-using System;
 using System.Diagnostics;
 using System.IO;
 using System.Reflection;
@@ -13,25 +12,9 @@ public static class Constant
         private static readonly Assembly Assembly = Assembly.GetExecutingAssembly();
         public static readonly string ProgramDirectory = Directory.GetParent(Assembly.Location.NonNull()).ToString();
         public static readonly string ExecutablePath = Path.Combine(ProgramDirectory, Wox + ".exe");
-
-        public static bool IsPortableMode;
-        public const string PortableFolderName = "UserData";
-        public static string PortableDataPath = Path.Combine(ProgramDirectory, PortableFolderName);
-        public static string DetermineDataDirectory()
-        {
-            if (Directory.Exists(PortableDataPath))
-            {
-                IsPortableMode = true;
-                return PortableDataPath;
-            }
-            else
-            {
-                return Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.ApplicationData), Wox);
-            }
-        }
-
-        public static readonly string DataDirectory = DetermineDataDirectory();
-        public static readonly string PluginsDirectory = Path.Combine(DataDirectory, Plugins);
+        public static readonly string ApplicationDirectory = Directory.GetParent(ProgramDirectory).ToString();
+        public static readonly string RootDirectory = Directory.GetParent(ApplicationDirectory).ToString();
+        
         public static readonly string PreinstalledDirectory = Path.Combine(ProgramDirectory, Plugins);
         public const string Issue = "https://github.com/jjw24/Wox/issues/new";
         public static readonly string Version = FileVersionInfo.GetVersionInfo(Assembly.Location.NonNull()).ProductVersion;
diff --git a/Wox.Infrastructure/Logger/Log.cs b/Wox.Infrastructure/Logger/Log.cs
index 349920076..4b7a97241 100644
--- a/Wox.Infrastructure/Logger/Log.cs
+++ b/Wox.Infrastructure/Logger/Log.cs
@@ -4,6 +4,7 @@
 using NLog;
 using NLog.Config;
 using NLog.Targets;
+using Wox.Infrastructure.UserSettings;
 
 namespace Wox.Infrastructure.Logger
 {
@@ -15,7 +16,7 @@ public static class Log
 
         static Log()
         {
-            CurrentLogDirectory = Path.Combine(Constant.DataDirectory, DirectoryName, Constant.Version);
+            CurrentLogDirectory = Path.Combine(DataLocation.DataDirectory(), DirectoryName, Constant.Version);
             if (!Directory.Exists(CurrentLogDirectory))
             {
                 Directory.CreateDirectory(CurrentLogDirectory);
diff --git a/Wox.Infrastructure/Storage/BinaryStorage.cs b/Wox.Infrastructure/Storage/BinaryStorage.cs
index d2c5a2da8..6f9031dde 100644
--- a/Wox.Infrastructure/Storage/BinaryStorage.cs
+++ b/Wox.Infrastructure/Storage/BinaryStorage.cs
@@ -5,6 +5,7 @@
 using System.Runtime.Serialization.Formatters;
 using System.Runtime.Serialization.Formatters.Binary;
 using Wox.Infrastructure.Logger;
+using Wox.Infrastructure.UserSettings;
 
 namespace Wox.Infrastructure.Storage
 {
@@ -17,7 +18,7 @@ public class BinaryStorage<T>
         public BinaryStorage(string filename)
         {
             const string directoryName = "Cache";
-            var directoryPath = Path.Combine(Constant.DataDirectory, directoryName);
+            var directoryPath = Path.Combine(DataLocation.DataDirectory(), directoryName);
             Helper.ValidateDirectory(directoryPath);
 
             const string fileSuffix = ".cache";
diff --git a/Wox.Infrastructure/Storage/PluginJsonStorage.cs b/Wox.Infrastructure/Storage/PluginJsonStorage.cs
index 27de500c7..77dd541c3 100644
--- a/Wox.Infrastructure/Storage/PluginJsonStorage.cs
+++ b/Wox.Infrastructure/Storage/PluginJsonStorage.cs
@@ -1,4 +1,5 @@
 using System.IO;
+using Wox.Infrastructure.UserSettings;
 
 namespace Wox.Infrastructure.Storage
 {
@@ -9,7 +10,7 @@ public PluginJsonStorage()
             // C# releated, add python releated below
             var dataType = typeof(T);
             var assemblyName = typeof(T).Assembly.GetName().Name;
-            DirectoryPath = Path.Combine(Constant.DataDirectory, DirectoryName, Constant.Plugins, assemblyName);
+            DirectoryPath = Path.Combine(DataLocation.DataDirectory(), DirectoryName, Constant.Plugins, assemblyName);
             Helper.ValidateDirectory(DirectoryPath);
 
             FilePath = Path.Combine(DirectoryPath, $"{dataType.Name}{FileSuffix}");
diff --git a/Wox.Infrastructure/Storage/WoxJsonStorage.cs b/Wox.Infrastructure/Storage/WoxJsonStorage.cs
index da0dbd073..1a6b22c4b 100644
--- a/Wox.Infrastructure/Storage/WoxJsonStorage.cs
+++ b/Wox.Infrastructure/Storage/WoxJsonStorage.cs
@@ -4,6 +4,7 @@
 using System.Linq;
 using System.Text;
 using System.Threading.Tasks;
+using Wox.Infrastructure.UserSettings;
 
 namespace Wox.Infrastructure.Storage
 {
@@ -11,7 +12,7 @@ namespace Wox.Infrastructure.Storage
     {
         public WoxJsonStorage()
         {
-            var directoryPath = Path.Combine(Constant.DataDirectory, DirectoryName);
+            var directoryPath = Path.Combine(DataLocation.DataDirectory(), DirectoryName);
             Helper.ValidateDirectory(directoryPath);
 
             var filename = typeof(T).Name;
diff --git a/Wox.Infrastructure/UserSettings/DataLocation.cs b/Wox.Infrastructure/UserSettings/DataLocation.cs
new file mode 100644
index 000000000..ef85341c5
--- /dev/null
+++ b/Wox.Infrastructure/UserSettings/DataLocation.cs
@@ -0,0 +1,34 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using System.Text;
+using System.Threading.Tasks;
+
+namespace Wox.Infrastructure.UserSettings
+{
+    public static class DataLocation
+    {
+        public const string PortableFolderName = "UserData";
+        public const string DeletionIndicatorFile = ".dead";
+        public static string PortableDataPath = Path.Combine(Constant.ProgramDirectory, PortableFolderName);
+        public static string RoamingDataPath = Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.ApplicationData), Constant.Wox);
+        public static string DataDirectory()
+        {
+            if (PortableDataLocationInUse())
+                return PortableDataPath;
+
+            return RoamingDataPath;
+        }
+
+        public static bool PortableDataLocationInUse()
+        {
+            if (Directory.Exists(PortableDataPath) && !File.Exists(DeletionIndicatorFile))
+                return true;
+
+            return false;
+        }
+
+        public static readonly string PluginsDirectory = Path.Combine(DataDirectory(), Constant.Plugins);
+    }
+}
diff --git a/Wox.Infrastructure/Wox.Infrastructure.csproj b/Wox.Infrastructure/Wox.Infrastructure.csproj
index fc1990da9..65bd29d49 100644
--- a/Wox.Infrastructure/Wox.Infrastructure.csproj
+++ b/Wox.Infrastructure/Wox.Infrastructure.csproj
@@ -77,7 +77,8 @@
     <Compile Include="UserSettings\PluginHotkey.cs" />
     <Compile Include="UserSettings\PluginSettings.cs" />
     <Compile Include="UserSettings\Settings.cs" />
-    <Compile Include="Wox.cs" />
+    <Compile Include="UserSettings\DataLocation.cs" />
+    <Compile Include="Constant.cs" />
   </ItemGroup>
   <ItemGroup>
     <ProjectReference Include="..\Wox.Plugin\Wox.Plugin.csproj">
diff --git a/Wox.Plugin/SharedCommands/FilesFolders.cs b/Wox.Plugin/SharedCommands/FilesFolders.cs
index 584a83bc6..f9eb13961 100644
--- a/Wox.Plugin/SharedCommands/FilesFolders.cs
+++ b/Wox.Plugin/SharedCommands/FilesFolders.cs
@@ -48,7 +48,7 @@ public static void Copy(this string sourcePath, string targetPath)
                 throw e;
 #else
                 MessageBox.Show(string.Format("Copying path {0} has failed, it will now be deleted for consistency", targetPath));
-                RemoveFolder(targetPath);
+                RemoveFolderIfExists(targetPath);
 #endif
             }
 
@@ -81,7 +81,7 @@ public static bool VerifyBothFolderFilesEqual(this string fromPath, string toPat
 
         }
 
-        public static void RemoveFolder(this string path)
+        public static void RemoveFolderIfExists(this string path)
         {
             try
             {
@@ -97,5 +97,15 @@ public static void RemoveFolder(this string path)
 #endif
             }
         }
+
+        public static bool LocationExists(this string path)
+        {
+            return Directory.Exists(path);
+        }
+
+        public static bool FileExits(this string filePath)
+        {
+            return File.Exists(filePath);
+        }
     }
 }
diff --git a/Wox/App.xaml.cs b/Wox/App.xaml.cs
index 0fc1e8c95..83a0d2255 100644
--- a/Wox/App.xaml.cs
+++ b/Wox/App.xaml.cs
@@ -4,6 +4,7 @@
 using System.Timers;
 using System.Windows;
 using Wox.Core;
+using Wox.Core.Configuration;
 using Wox.Core.Plugin;
 using Wox.Core.Resource;
 using Wox.Helper;
@@ -26,6 +27,7 @@ public partial class App : IDisposable, ISingleInstanceApp
         private MainViewModel _mainVM;
         private SettingWindowViewModel _settingsVM;
         private readonly Updater _updater = new Updater(Wox.Properties.Settings.Default.GithubRepo);
+        private readonly Portable _portable = new Portable();
         private readonly Alphabet _alphabet = new Alphabet();
         private StringMatcher _stringMatcher;
 
@@ -46,6 +48,8 @@ private void OnStartup(object sender, StartupEventArgs e)
         {
             Stopwatch.Normal("|App.OnStartup|Startup cost", () =>
             {
+                _portable.PreStartCleanUpAfterPortabilityUpdate();
+
                 Log.Info("|App.OnStartup|Begin Wox startup ----------------------------------------------------");
                 Log.Info($"|App.OnStartup|Runtime info:{ErrorReporting.RuntimeInfo()}");
                 RegisterAppDomainExceptions();
@@ -53,7 +57,7 @@ private void OnStartup(object sender, StartupEventArgs e)
 
                 ImageLoader.Initialize();
 
-                _settingsVM = new SettingWindowViewModel(_updater);
+                _settingsVM = new SettingWindowViewModel(_updater, _portable);
                 _settings = _settingsVM.Settings;
 
                 _alphabet.Initialize(_settings);
diff --git a/Wox/SettingWindow.xaml b/Wox/SettingWindow.xaml
index 3c12bda6f..bbb17d506 100644
--- a/Wox/SettingWindow.xaml
+++ b/Wox/SettingWindow.xaml
@@ -33,6 +33,9 @@
     <TabControl Height="auto" SelectedIndex="0">
         <TabItem Header="{DynamicResource general}">
             <StackPanel Orientation="Vertical">
+                <CheckBox Margin="10" IsChecked="{Binding PortableMode}">
+                    <TextBlock Text="Portable Mode" />
+                </CheckBox>
                 <CheckBox Margin="10" IsChecked="{Binding Settings.StartWoxOnSystemStartup}"
                           Checked="OnAutoStartupChecked" Unchecked="OnAutoStartupUncheck">
                     <TextBlock Text="{DynamicResource startWoxOnSystemStartup}" />
diff --git a/Wox/ViewModel/SettingWindowViewModel.cs b/Wox/ViewModel/SettingWindowViewModel.cs
index f9160df9f..3f315a9e3 100644
--- a/Wox/ViewModel/SettingWindowViewModel.cs
+++ b/Wox/ViewModel/SettingWindowViewModel.cs
@@ -8,11 +8,11 @@
 using System.Windows.Media;
 using System.Windows.Media.Imaging;
 using Wox.Core;
+using Wox.Core.Configuration;
 using Wox.Core.Plugin;
 using Wox.Core.Resource;
 using Wox.Helper;
 using Wox.Infrastructure;
-using Wox.Infrastructure.Http;
 using Wox.Infrastructure.Storage;
 using Wox.Infrastructure.UserSettings;
 using Wox.Plugin;
@@ -22,11 +22,13 @@ namespace Wox.ViewModel
     public class SettingWindowViewModel : BaseModel
     {
         private readonly Updater _updater;
+        private readonly IPortable _portable;
         private readonly WoxJsonStorage<Settings> _storage;
 
-        public SettingWindowViewModel(Updater updater)
+        public SettingWindowViewModel(Updater updater, IPortable portable)
         {
             _updater = updater;
+            _portable = portable;
             _storage = new WoxJsonStorage<Settings>();
             Settings = _storage.Load();
             Settings.PropertyChanged += (s, e) =>
@@ -36,8 +38,6 @@ public SettingWindowViewModel(Updater updater)
                     OnPropertyChanged(nameof(ActivatedTimes));
                 }
             };
-
-
         }
 
         public Settings Settings { get; set; }
@@ -47,6 +47,27 @@ public async void UpdateApp()
             await _updater.UpdateApp(false);
         }
 
+        // This is only required to set at startup. When portable mode enabled/disabled a restart is always required
+        private bool _portableMode = DataLocation.PortableDataLocationInUse();
+        public bool PortableMode
+        {
+            get { return _portableMode; }
+            set
+            {
+                if (!_portable.CanUpdatePortability())
+                    return;
+
+                if (DataLocation.PortableDataLocationInUse())
+                {
+                    _portable.DisablePortableMode();
+                }
+                else
+                {
+                    _portable.EnablePortableMode();
+                }
+            }
+        }
+
         public void Save()
         {
             _storage.Save();