diff --git a/server/src/os/windows/registry.cpp b/server/src/os/windows/registry.cpp
new file mode 100644
index 00000000..29469f25
--- /dev/null
+++ b/server/src/os/windows/registry.cpp
@@ -0,0 +1,97 @@
+/**
+ * server/src/os/windows/registry.cpp
+ *
+ * This file is part of the traintastic source code.
+ *
+ * Copyright (C) 2022 Reinder Feenstra
+ *
+ * This program is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU General Public License
+ * as published by the Free Software Foundation; either version 2
+ * of the License, or (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU General Public License for more details.
+ *
+ * You should have received a copy of the GNU General Public License
+ * along with this program; if not, write to the Free Software
+ * Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+ */
+
+#include "registry.hpp"
+#include <string>
+#include <windows.h>
+
+namespace Windows::Registry {
+
+const char* runKey = "SOFTWARE\\Microsoft\\Windows\\CurrentVersion\\Run";
+//const char* runTraintasticServerKey = "SOFTWARE\\Microsoft\\Windows\\CurrentVersion\\Run\\TraintasticServer";
+const char* startupApprovedKey = "SOFTWARE\\Microsoft\\Windows\\CurrentVersion\\Explorer\\StartupApproved\\Run";
+const char* traintasticServerKey = "TraintasticServer";
+const WCHAR* traintasticServerKeyW = L"TraintasticServer";
+const DWORD startupEnabled = 2;
+const DWORD startupDisabled = 3;
+
+bool addRun()
+{
+  bool success = false;
+  HKEY key;
+  LSTATUS r = RegOpenKeyExA(HKEY_CURRENT_USER, runKey, 0, KEY_WRITE, &key);
+  if(r == ERROR_SUCCESS)
+  {
+    std::basic_string<WCHAR> path;
+    path.resize(MAX_PATH);
+    path[0] = '"';
+    const DWORD l = GetModuleFileNameW(nullptr, path.data() + 1, path.size() - 1);
+    if(l > 0)
+    {
+      path.resize(1 + l);
+      path.append(L"\" --tray");
+
+      r = RegSetValueExW(key, traintasticServerKeyW, 0, REG_SZ, reinterpret_cast<const BYTE*>(path.c_str()), (path.size() + 1) * sizeof(WCHAR));
+      success = (r == ERROR_SUCCESS);
+    }
+    RegCloseKey(key);
+  }
+  return success;
+}
+
+bool getStartUpApproved(bool& enabled)
+{
+  bool success = false;
+  HKEY key;
+  LSTATUS r = RegOpenKeyExA(HKEY_CURRENT_USER, startupApprovedKey, 0, KEY_READ, &key);
+  if(r == ERROR_SUCCESS)
+  {
+    DWORD data[3];
+    DWORD size = sizeof(data);
+    r = RegGetValueA(key, nullptr, traintasticServerKey, RRF_RT_REG_BINARY, nullptr, &data, &size);
+    if(r == ERROR_SUCCESS)
+    {
+      enabled = (data[0] == startupEnabled);
+      success = true;
+    }
+    RegCloseKey(key);
+  }
+  return success;
+}
+
+bool setStartUpApproved(bool enabled)
+{
+  bool success = false;
+  HKEY key;
+  LSTATUS r = RegOpenKeyExA(HKEY_CURRENT_USER, startupApprovedKey, 0, KEY_WRITE, &key);
+  if(r == ERROR_SUCCESS)
+  {
+    DWORD data[3] = {enabled ? startupEnabled : startupDisabled, 0, 0};
+    DWORD size = sizeof(data);
+    r = RegSetValueExA(key, traintasticServerKey, 0, REG_BINARY, reinterpret_cast<const BYTE*>(&data), size);
+    success = (r == ERROR_SUCCESS);
+    RegCloseKey(key);
+  }
+  return success;
+}
+
+}
diff --git a/server/src/os/windows/registry.hpp b/server/src/os/windows/registry.hpp
new file mode 100644
index 00000000..884bbfc3
--- /dev/null
+++ b/server/src/os/windows/registry.hpp
@@ -0,0 +1,35 @@
+/**
+ * server/src/os/windows/registry.hpp
+ *
+ * This file is part of the traintastic source code.
+ *
+ * Copyright (C) 2022 Reinder Feenstra
+ *
+ * This program is free software; you can redistribute it and/or
+ * modify it under the terms of the GNU General Public License
+ * as published by the Free Software Foundation; either version 2
+ * of the License, or (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU General Public License for more details.
+ *
+ * You should have received a copy of the GNU General Public License
+ * along with this program; if not, write to the Free Software
+ * Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA  02110-1301, USA.
+ */
+
+#ifndef TRAINTASTIC_SERVER_OS_WINDOWS_REGISTRY_HPP
+#define TRAINTASTIC_SERVER_OS_WINDOWS_REGISTRY_HPP 
+
+namespace Windows::Registry {
+
+bool addRun();
+
+bool getStartUpApproved(bool& enabled);
+bool setStartUpApproved(bool enabled);
+
+}
+
+#endif
diff --git a/server/src/os/windows/trayicon.cpp b/server/src/os/windows/trayicon.cpp
index c2ec836b..97e3c228 100644
--- a/server/src/os/windows/trayicon.cpp
+++ b/server/src/os/windows/trayicon.cpp
@@ -25,6 +25,7 @@
 #include <version.hpp>
 #include <traintastic/codename.hpp>
 #include "consolewindow.hpp"
+#include "registry.hpp"
 #include "../../core/eventloop.hpp"
 #include "../../traintastic/traintastic.hpp"
 #include "../../utils/setthreadname.hpp"
@@ -79,9 +80,15 @@ void TrayIcon::run()
   menuAddItem(MenuItem::AllowClientServerRestart, "Allow client to restart server");
   menuAddItem(MenuItem::AllowClientServerShutdown, "Allow client to shutdown server");
   menuAddSeperator();
+  menuAddItem(MenuItem::StartAutomaticallyAtLogon, "Start automatically at logon");
+  menuAddSeperator();
   menuAddItem(MenuItem::Restart, "Restart");
   menuAddItem(MenuItem::Shutdown, "Shutdown");
 
+  bool startUpApproved = false;
+  Registry::getStartUpApproved(startUpApproved);
+  menuSetItemChecked(MenuItem::StartAutomaticallyAtLogon, startUpApproved);  
+
   // setup tray icon:
   static NOTIFYICONDATA notifyIconData;
   memset(&notifyIconData, 0, sizeof(notifyIconData));
@@ -206,6 +213,16 @@ LRESULT CALLBACK TrayIcon::windowProc(_In_ HWND hWnd, _In_ UINT uMsg, _In_ WPARA
           });
         break;
       }
+      case MenuItem::StartAutomaticallyAtLogon:
+      {
+        bool startUpApproved = !menuGetItemChecked(MenuItem::StartAutomaticallyAtLogon);
+        if(startUpApproved)
+          Registry::addRun();
+        Registry::setStartUpApproved(startUpApproved);
+        if(Registry::getStartUpApproved(startUpApproved))
+          menuSetItemChecked(MenuItem::StartAutomaticallyAtLogon, startUpApproved);
+        break;
+      }
     }
     break;
 
@@ -245,6 +262,12 @@ void TrayIcon::menuAddSeperator()
   InsertMenuItem(s_menu, GetMenuItemCount(s_menu), TRUE, &item);
 }
 
+bool TrayIcon::menuGetItemChecked(MenuItem id)
+{
+  assert(s_menu);
+  return GetMenuState(s_menu, static_cast<UINT>(id), MF_BYCOMMAND) & MF_CHECKED;
+}
+
 void TrayIcon::menuSetItemChecked(MenuItem id, bool checked)
 {
   assert(s_menu);
diff --git a/server/src/os/windows/trayicon.hpp b/server/src/os/windows/trayicon.hpp
index bfdcb958..fae41a64 100644
--- a/server/src/os/windows/trayicon.hpp
+++ b/server/src/os/windows/trayicon.hpp
@@ -46,6 +46,7 @@ class TrayIcon
       ShowHideConsole = 3,
       AllowClientServerRestart = 4,
       AllowClientServerShutdown = 5,
+      StartAutomaticallyAtLogon = 6,
     };
 
     struct TraintasticSettings
@@ -68,6 +69,7 @@ class TrayIcon
 
     static void menuAddItem(MenuItem id, const LPSTR text, bool enabled = true);
     static void menuAddSeperator();
+    static bool menuGetItemChecked(MenuItem id);
     static void menuSetItemChecked(MenuItem id, bool checked);
 
     static void getSettings();