diff --git a/src/NzbDrone.Common.Test/PathExtensionFixture.cs b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
index 6e35561ff..58d71586f 100644
--- a/src/NzbDrone.Common.Test/PathExtensionFixture.cs
+++ b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
@@ -263,7 +263,7 @@ namespace NzbDrone.Common.Test
         [Test]
         public void GetUpdateClientExePath()
         {
-            GetIAppDirectoryInfo().GetUpdateClientExePath().Should().BeEquivalentTo(@"C:\Temp\radarr_update\Radarr.Update.exe".AsOsAgnostic());
+            GetIAppDirectoryInfo().GetUpdateClientExePath(new Version("0.2.0.1480")).Should().BeEquivalentTo(@"C:\Temp\radarr_update\Radarr.Update.exe".AsOsAgnostic());
         }
 
         [Test]
diff --git a/src/NzbDrone.Common/Extensions/PathExtensions.cs b/src/NzbDrone.Common/Extensions/PathExtensions.cs
index e5f01f095..dea644755 100644
--- a/src/NzbDrone.Common/Extensions/PathExtensions.cs
+++ b/src/NzbDrone.Common/Extensions/PathExtensions.cs
@@ -192,12 +192,12 @@ namespace NzbDrone.Common.Extensions
             return directories;
         }
 
-        public static string ProcessNameToExe(this string processName)
+        private static string ProcessNameToExe(this string processName, Version version)
         {
             // 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)
+            if (OsInfo.IsWindows || OsInfo.IsLinux || version.Major == 0)
             {
                 processName += ".exe";
             }
@@ -272,9 +272,9 @@ namespace NzbDrone.Common.Extensions
             }
         }
 
-        public static string GetUpdateClientExePath(this IAppFolderInfo appFolderInfo)
+        public static string GetUpdateClientExePath(this IAppFolderInfo appFolderInfo, Version version)
         {
-            return Path.Combine(GetUpdateSandboxFolder(appFolderInfo), UPDATE_CLIENT_EXE_NAME).ProcessNameToExe();
+            return Path.Combine(GetUpdateSandboxFolder(appFolderInfo), UPDATE_CLIENT_EXE_NAME).ProcessNameToExe(version);
         }
 
         public static string GetBackupFolder(this IAppFolderInfo appFolderInfo)
diff --git a/src/NzbDrone.Core/Update/InstallUpdateService.cs b/src/NzbDrone.Core/Update/InstallUpdateService.cs
index 0cfa26cab..c2d6df5ba 100644
--- a/src/NzbDrone.Core/Update/InstallUpdateService.cs
+++ b/src/NzbDrone.Core/Update/InstallUpdateService.cs
@@ -131,13 +131,13 @@ namespace NzbDrone.Core.Update
             // Set executable flag on update app
             if (OsInfo.IsOsx)
             {
-                _diskProvider.SetPermissions(_appFolderInfo.GetUpdateClientExePath(), "0755", null, null);
+                _diskProvider.SetPermissions(_appFolderInfo.GetUpdateClientExePath(updatePackage.Version), "0755", null, null);
             }
 
-            _logger.Info("Starting update client {0}", _appFolderInfo.GetUpdateClientExePath());
+            _logger.Info("Starting update client {0}", _appFolderInfo.GetUpdateClientExePath(updatePackage.Version));
             _logger.ProgressInfo("Radarr will restart shortly.");
 
-            _processProvider.Start(_appFolderInfo.GetUpdateClientExePath(), GetUpdaterArgs(updateSandboxFolder));
+            _processProvider.Start(_appFolderInfo.GetUpdateClientExePath(updatePackage.Version), GetUpdaterArgs(updateSandboxFolder));
         }
 
         private void EnsureValidBranch(UpdatePackage package)