diff --git a/README.md b/README.md
index b60089cbe..44dd4fac7 100644
--- a/README.md
+++ b/README.md
@@ -17,7 +17,7 @@ Developer note: The software implements the [Torznab](https://github.com/Sonarr/
 
 #### Supported Systems
 * Windows using .NET 4.6.1 or above [Download here](https://www.microsoft.com/net/framework/versions/net461).
-* Linux and macOS using Mono 5.8 or above. [Download here](http://www.mono-project.com/download/). Earlier versions of mono may work, but some trackers may fail to negotiate SSL correctly, and others may cause Jackett to crash when used.
+* Linux and macOS using Mono 5.8 or above. [Download here](http://www.mono-project.com/download/).
 
 ### Supported Public Trackers
  * 1337x
diff --git a/src/Jackett.Common/Services/UpdateService.cs b/src/Jackett.Common/Services/UpdateService.cs
index a3c808d1d..56f538280 100644
--- a/src/Jackett.Common/Services/UpdateService.cs
+++ b/src/Jackett.Common/Services/UpdateService.cs
@@ -270,15 +270,27 @@ namespace Jackett.Common.Services
 
         private void StartUpdate(string updaterExePath, string installLocation, bool isWindows, bool NoRestart, bool trayWasRunning)
         {
+            string appType = "Console";
+            //DI once off Owin
+            IProcessService processService = new ProcessService(logger);
+            IServiceConfigService windowsService = new WindowsServiceConfigService(processService, logger);
+
+            if (isWindows && windowsService.ServiceExists())
+            {
+                appType = "WindowsService";
+            }
+
             var exe = Path.GetFileName(ExePath());
             var args = string.Join(" ", Environment.GetCommandLineArgs().Skip(1).Select(a => a.Contains(" ") ? "\"" +a + "\"" : a )).Replace("\"", "\\\"");
 
             var startInfo = new ProcessStartInfo();
+            startInfo.UseShellExecute = false;
+            startInfo.CreateNoWindow = true;
 
             // Note: add a leading space to the --Args argument to avoid parsing as arguments
             if (isWindows)
             {
-                startInfo.Arguments = $"--Path \"{installLocation}\" --Type \"{exe}\" --Args \" {args}\"";
+                startInfo.Arguments = $"--Path \"{installLocation}\" --Type \"{appType}\" --Args \" {args}\"";
                 startInfo.FileName = Path.Combine(updaterExePath);
             }
             else
@@ -287,13 +299,12 @@ namespace Jackett.Common.Services
                 args = exe + " " + args;
                 exe = "mono";
 
-                startInfo.Arguments = $"{Path.Combine(updaterExePath)} --Path \"{installLocation}\" --Type \"{exe}\" --Args \" {args}\"";
+                startInfo.Arguments = $"{Path.Combine(updaterExePath)} --Path \"{installLocation}\" --Type \"{appType}\" --Args \" {args}\"";
                 startInfo.FileName = "mono";
-                startInfo.UseShellExecute = false;
-                startInfo.CreateNoWindow = true;
             }
 
-            try { 
+            try
+            {
                 var pid = Process.GetCurrentProcess().Id;
                 startInfo.Arguments += $" --KillPids \"{pid}\"";
             }
@@ -317,7 +328,7 @@ namespace Jackett.Common.Services
             var procInfo = Process.Start(startInfo);
             logger.Info($"Updater started process id: {procInfo.Id}");
             if (NoRestart == false)
-            { 
+            {
                 logger.Info("Exiting Jackett..");
                 lockService.Signal();
                 //TODO: Remove once off Owin
diff --git a/src/Jackett.Service/Service.cs b/src/Jackett.Service/Service.cs
index ba95ec746..7fdd7fd22 100644
--- a/src/Jackett.Service/Service.cs
+++ b/src/Jackett.Service/Service.cs
@@ -77,10 +77,12 @@ namespace Jackett.Service
 
         private void ProcessExited(object sender, EventArgs e)
         {
+            logger.Info("Console process exited");
+
             if (!serviceStopInitiated)
             {
                 logger.Info("Service stop not responsible for process exit");
-                OnStop();
+                Stop();
             }
         }
 
@@ -89,7 +91,7 @@ namespace Jackett.Service
             if (consoleProcess != null && !consoleProcess.HasExited)
             {
                 consoleProcess.StandardInput.Close();
-                System.Threading.Thread.Sleep(1000);
+                consoleProcess.WaitForExit(2000);
                 if (consoleProcess != null && !consoleProcess.HasExited)
                 {
                     consoleProcess.Kill();
diff --git a/src/Jackett.Tray/Jackett.Tray.csproj b/src/Jackett.Tray/Jackett.Tray.csproj
index f48380428..88c8c5d10 100644
--- a/src/Jackett.Tray/Jackett.Tray.csproj
+++ b/src/Jackett.Tray/Jackett.Tray.csproj
@@ -66,6 +66,7 @@
     </Compile>
     <Compile Include="Program.cs" />
     <Compile Include="Properties\AssemblyInfo.cs" />
+    <Compile Include="TrayConsoleOptions.cs" />
     <EmbeddedResource Include="Main.resx">
       <DependentUpon>Main.cs</DependentUpon>
     </EmbeddedResource>
@@ -109,6 +110,11 @@
       <EmbedInteropTypes>True</EmbedInteropTypes>
     </COMReference>
   </ItemGroup>
+  <ItemGroup>
+    <PackageReference Include="CommandLineParser">
+      <Version>2.2.1</Version>
+    </PackageReference>
+  </ItemGroup>
   <Import Project="$(MSBuildToolsPath)\Microsoft.CSharp.targets" />
   <!-- To modify your build process, add your task inside one of the targets below and uncomment it. 
        Other similar extension points exist, see Microsoft.Common.targets.
diff --git a/src/Jackett.Tray/Main.cs b/src/Jackett.Tray/Main.cs
index 68283890e..c78655344 100644
--- a/src/Jackett.Tray/Main.cs
+++ b/src/Jackett.Tray/Main.cs
@@ -25,7 +25,7 @@ namespace Jackett.Tray
         private Logger logger;
         private bool closeApplicationInitiated;
 
-        public Main()
+        public Main(string updatedVersion)
         {
             Hide();
             InitializeComponent();
@@ -65,12 +65,22 @@ namespace Jackett.Tray
                 StartConsoleApplication();
             }
 
+            if (!string.IsNullOrWhiteSpace(updatedVersion))
+            {
+                notifyIcon1.BalloonTipTitle = "Jackett";
+                notifyIcon1.BalloonTipText = $"Jackett has updated to version {updatedVersion}";
+                notifyIcon1.BalloonTipIcon = ToolTipIcon.Info;
+                notifyIcon1.ShowBalloonTip(10000);
+                logger.Info($"Display balloon tip, updated to {updatedVersion}");
+            }
+
             Task.Factory.StartNew(WaitForEvent);
         }
 
         private void WaitForEvent()
         {
             trayLockService.WaitForSignal();
+            logger.Info("Received signal from tray lock service");
             CloseTrayApplication();
         }
 
diff --git a/src/Jackett.Tray/Program.cs b/src/Jackett.Tray/Program.cs
index 75ad47e4d..8d01ddabc 100644
--- a/src/Jackett.Tray/Program.cs
+++ b/src/Jackett.Tray/Program.cs
@@ -1,4 +1,5 @@
-using System;
+using CommandLine;
+using System;
 using System.Diagnostics;
 using System.Linq;
 using System.Windows.Forms;
@@ -11,7 +12,7 @@ namespace Jackett.Tray
         /// The main entry point for the application.
         /// </summary>
         [STAThread]
-        static void Main()
+        static void Main(string[] args)
         {
             var JacketTrayProcess = Process.GetCurrentProcess();
             var runningProcesses = Process.GetProcesses();
@@ -23,10 +24,29 @@ namespace Jackett.Tray
                 MessageBox.Show("JackettTray is already running");
             }
             else
-            { 
+            {
+                string newVersion = "";
+                var commandLineParser = new Parser(settings => settings.CaseSensitive = false);
+
+                try
+                {
+                    var optionsResult = commandLineParser.ParseArguments<TrayConsoleOptions>(args);
+                    optionsResult.WithParsed(options =>
+                    {
+                        if (!string.IsNullOrWhiteSpace(options.UpdatedVersion))
+                        {
+                            newVersion = options.UpdatedVersion;
+                        }
+                    });
+                }
+                catch (Exception e)
+                {
+                    newVersion = "";
+                }
+
                 Application.EnableVisualStyles();
                 Application.SetCompatibleTextRenderingDefault(false);
-                Application.Run(new Main());
+                Application.Run(new Main(newVersion));
             }
         }
     }
diff --git a/src/Jackett.Tray/TrayConsoleOptions.cs b/src/Jackett.Tray/TrayConsoleOptions.cs
new file mode 100644
index 000000000..02f3ac4b0
--- /dev/null
+++ b/src/Jackett.Tray/TrayConsoleOptions.cs
@@ -0,0 +1,10 @@
+using CommandLine;
+
+namespace Jackett.Tray
+{
+    public class TrayConsoleOptions
+    {
+        [Option("UpdatedVersion", HelpText = "Indicates the new version that Jackett just updated to so that user understands why they are getting a prompt to start Windows service")]
+        public string UpdatedVersion { get; set; }
+    }
+}
diff --git a/src/Jackett.Updater/Program.cs b/src/Jackett.Updater/Program.cs
index 16a0a8025..f8b29253a 100644
--- a/src/Jackett.Updater/Program.cs
+++ b/src/Jackett.Updater/Program.cs
@@ -38,6 +38,14 @@ namespace Jackett.Updater
             logger.Info("Jackett Updater v" + GetCurrentVersion());
             logger.Info("Options \"" + string.Join("\" \"", args) + "\"");
 
+            bool isWindows = Environment.OSVersion.Platform == PlatformID.Win32NT;
+            if (isWindows)
+            {
+                //The updater starts before Jackett closes
+                logger.Info("Pausing for 3 seconds to give Jackett & tray time to shutdown");
+                System.Threading.Tasks.Task.Delay(3000);
+            }
+         
             processService = new ProcessService(logger);
             windowsService = new WindowsServiceConfigService(processService, logger);
 
@@ -248,15 +256,16 @@ namespace Jackett.Updater
 
             if (options.NoRestart == false)
             {
-                if (trayRunning || options.StartTray)
+                if (isWindows && (trayRunning || options.StartTray))
                 {
                     var startInfo = new ProcessStartInfo()
                     {
-                        Arguments = options.Args,
+                        Arguments = $"--UpdatedVersion \" {EnvironmentUtil.JackettVersion}\"",
                         FileName = Path.Combine(options.Path, "JackettTray.exe"),
                         UseShellExecute = true
                     };
 
+                    logger.Info("Starting Tray: " + startInfo.FileName + " " + startInfo.Arguments);
                     Process.Start(startInfo);
 
                     if (!windowsService.ServiceExists())
@@ -266,12 +275,27 @@ namespace Jackett.Updater
                     }
                 }
 
-                if (string.Equals(options.Type, "JackettService.exe", StringComparison.InvariantCultureIgnoreCase))
+                if (string.Equals(options.Type, "WindowsService", StringComparison.InvariantCultureIgnoreCase))
                 {
-                    if (windowsService.ServiceExists())
+                    logger.Info("Starting Windows service");
+
+                    if (ServerUtil.IsUserAdministrator())
                     {
                         windowsService.Start();
                     }
+                    else
+                    {
+                        try
+                        {
+                            var consolePath = Path.Combine(options.Path, "JackettConsole.exe");
+                            processService.StartProcessAndLog(consolePath, "--Start", true);
+                        }
+                        catch
+                        {
+                            logger.Error("Failed to get admin rights to start the service.");
+                        }
+                    }
+
                 }
                 else
                 {