diff --git a/src/NzbDrone.Common.Test/PathExtensionFixture.cs b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
index 5fa373e12..6e35561ff 100644
--- a/src/NzbDrone.Common.Test/PathExtensionFixture.cs
+++ b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.IO;
 using FluentAssertions;
 using Moq;
@@ -257,7 +257,7 @@ namespace NzbDrone.Common.Test
         [Test]
         public void GetUpdateClientFolder()
         {
-            GetIAppDirectoryInfo().GetUpdateClientFolder().Should().BeEquivalentTo(@"C:\Temp\radarr_update\Radarr\NzbDrone.Update\".AsOsAgnostic());
+            GetIAppDirectoryInfo().GetUpdateClientFolder(new Version("0.2.0.1480")).Should().BeEquivalentTo(@"C:\Temp\radarr_update\Radarr\NzbDrone.Update\".AsOsAgnostic());
         }
 
         [Test]
diff --git a/src/NzbDrone.Common/Extensions/PathExtensions.cs b/src/NzbDrone.Common/Extensions/PathExtensions.cs
index 34fc833f7..e5f01f095 100644
--- a/src/NzbDrone.Common/Extensions/PathExtensions.cs
+++ b/src/NzbDrone.Common/Extensions/PathExtensions.cs
@@ -14,7 +14,7 @@ namespace NzbDrone.Common.Extensions
         private const string NZBDRONE_DB = "nzbdrone.db";
         private const string NZBDRONE_LOG_DB = "logs.db";
         private const string NLOG_CONFIG_FILE = "nlog.config";
-        private const string UPDATE_CLIENT_EXE = "Radarr.Update.exe";
+        private const string UPDATE_CLIENT_EXE_NAME = "Radarr.Update";
         private const string BACKUP_FOLDER = "Backups";
 
         private static readonly string UPDATE_SANDBOX_FOLDER_NAME = "radarr_update" + Path.DirectorySeparatorChar;
@@ -22,6 +22,7 @@ namespace NzbDrone.Common.Extensions
         private static readonly string UPDATE_BACKUP_FOLDER_NAME = "radarr_backup" + Path.DirectorySeparatorChar;
         private static readonly string UPDATE_BACKUP_APPDATA_FOLDER_NAME = "radarr_appdata_backup" + Path.DirectorySeparatorChar;
         private static readonly string UPDATE_CLIENT_FOLDER_NAME = "NzbDrone.Update" + Path.DirectorySeparatorChar;
+        private static readonly string UPDATE_V3_CLIENT_FOLDER_NAME = "Radarr.Update" + Path.DirectorySeparatorChar;
         private static readonly string UPDATE_LOG_FOLDER_NAME = "UpdateLogs" + Path.DirectorySeparatorChar;
 
         public static string CleanFilePath(this string path)
@@ -191,6 +192,19 @@ namespace NzbDrone.Common.Extensions
             return directories;
         }
 
+        public static string ProcessNameToExe(this string processName)
+        {
+            // Windows always has exe (but is shunted to net core)
+            // Linux is kept on mono pending manual upgrade to net core so has .exe
+            // macOS is shunted to net core and does not have .exe
+            if (OsInfo.IsWindows || OsInfo.IsLinux)
+            {
+                processName += ".exe";
+            }
+
+            return processName;
+        }
+
         public static string GetAppDataPath(this IAppFolderInfo appFolderInfo)
         {
             return appFolderInfo.AppDataFolder;
@@ -246,14 +260,21 @@ namespace NzbDrone.Common.Extensions
             return Path.Combine(GetUpdateSandboxFolder(appFolderInfo), UPDATE_PACKAGE_FOLDER_NAME);
         }
 
-        public static string GetUpdateClientFolder(this IAppFolderInfo appFolderInfo)
+        public static string GetUpdateClientFolder(this IAppFolderInfo appFolderInfo, Version version)
         {
-            return Path.Combine(GetUpdatePackageFolder(appFolderInfo), UPDATE_CLIENT_FOLDER_NAME);
+            if (version.Major >= 3)
+            {
+                return Path.Combine(GetUpdatePackageFolder(appFolderInfo), UPDATE_V3_CLIENT_FOLDER_NAME);
+            }
+            else
+            {
+                return Path.Combine(GetUpdatePackageFolder(appFolderInfo), UPDATE_CLIENT_FOLDER_NAME);
+            }
         }
 
         public static string GetUpdateClientExePath(this IAppFolderInfo appFolderInfo)
         {
-            return Path.Combine(GetUpdateSandboxFolder(appFolderInfo), UPDATE_CLIENT_EXE);
+            return Path.Combine(GetUpdateSandboxFolder(appFolderInfo), UPDATE_CLIENT_EXE_NAME).ProcessNameToExe();
         }
 
         public static string GetBackupFolder(this IAppFolderInfo appFolderInfo)
diff --git a/src/NzbDrone.Core.Test/UpdateTests/UpdateServiceFixture.cs b/src/NzbDrone.Core.Test/UpdateTests/UpdateServiceFixture.cs
index f83924208..be5c3fb7e 100644
--- a/src/NzbDrone.Core.Test/UpdateTests/UpdateServiceFixture.cs
+++ b/src/NzbDrone.Core.Test/UpdateTests/UpdateServiceFixture.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.IO;
 using FluentAssertions;
@@ -131,7 +131,7 @@ namespace NzbDrone.Core.Test.UpdateTests
         [Test]
         public void Should_copy_update_client_to_root_of_sandbox()
         {
-            var updateClientFolder = Mocker.GetMock<IAppFolderInfo>().Object.GetUpdateClientFolder();
+            var updateClientFolder = Mocker.GetMock<IAppFolderInfo>().Object.GetUpdateClientFolder(It.IsAny<Version>());
 
             Subject.Execute(new ApplicationUpdateCommand());
 
diff --git a/src/NzbDrone.Core/Update/InstallUpdateService.cs b/src/NzbDrone.Core/Update/InstallUpdateService.cs
index e42a075cd..ee3e942f3 100644
--- a/src/NzbDrone.Core/Update/InstallUpdateService.cs
+++ b/src/NzbDrone.Core/Update/InstallUpdateService.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using System.Collections.Generic;
 using System.IO;
 using NLog;
@@ -121,12 +121,12 @@ namespace NzbDrone.Core.Update
 
             if (OsInfo.IsNotWindows && _configFileProvider.UpdateMechanism == UpdateMechanism.Script)
             {
-                InstallUpdateWithScript(updateSandboxFolder);
+                InstallUpdateWithScript(updateSandboxFolder, updatePackage.Version);
                 return;
             }
 
             _logger.Info("Preparing client");
-            _diskTransferService.TransferFolder(_appFolderInfo.GetUpdateClientFolder(), updateSandboxFolder, TransferMode.Move, false);
+            _diskTransferService.TransferFolder(_appFolderInfo.GetUpdateClientFolder(updatePackage.Version), updateSandboxFolder, TransferMode.Move, false);
 
             _logger.Info("Starting update client {0}", _appFolderInfo.GetUpdateClientExePath());
             _logger.ProgressInfo("Radarr will restart shortly.");
@@ -153,7 +153,7 @@ namespace NzbDrone.Core.Update
             }
         }
 
-        private void InstallUpdateWithScript(string updateSandboxFolder)
+        private void InstallUpdateWithScript(string updateSandboxFolder, Version version)
         {
             var scriptPath = _configFileProvider.UpdateScriptPath;
 
@@ -168,7 +168,7 @@ namespace NzbDrone.Core.Update
             }
 
             _logger.Info("Removing NzbDrone.Update");
-            _diskProvider.DeleteFolder(_appFolderInfo.GetUpdateClientFolder(), true);
+            _diskProvider.DeleteFolder(_appFolderInfo.GetUpdateClientFolder(version), true);
 
             _logger.ProgressInfo("Starting update script: {0}", _configFileProvider.UpdateScriptPath);
             _processProvider.Start(scriptPath, GetUpdaterArgs(updateSandboxFolder));