diff --git a/doc/user/configuration.md b/doc/user/configuration.md
index c13580648..6350eb2f1 100644
--- a/doc/user/configuration.md
+++ b/doc/user/configuration.md
@@ -105,6 +105,7 @@ This section contains options used by the GUI it will begin with `[gui]`
 | windowGeometry                 | QRect             | Geometry of the window used to restore the window geometry after exiting the app |
 | showGenericClientFailureDialog | `true` or `false` | When `true` client connection errors will not show popup error messages [default: true] |
 | shownFirstConnectedMessage     | `true` or `false` | When `true` GUI has shown the user the message for connecting the first time [default: false] |
+| shownServerFirstStartMessage   | `true` or `false` | When `true` GUI has shown the user the Deskflow server is now running message [default: false] |
 
 ### Log
 
diff --git a/src/lib/common/Settings.h b/src/lib/common/Settings.h
index 33235afcd..4cfe8e601 100644
--- a/src/lib/common/Settings.h
+++ b/src/lib/common/Settings.h
@@ -74,6 +74,7 @@ public:
     inline static const auto WindowGeometry = QStringLiteral("gui/windowGeometry");
     inline static const auto ShowGenericClientFailureDialog = QStringLiteral("gui/showGenericClientFailureDialog");
     inline static const auto ShownFirstConnectedMessage = QStringLiteral("gui/shownFirstConnectedMessage");
+    inline static const auto ShownServerFirstStartMessage = QStringLiteral("gui/shownServerFirstStartMessage");
   };
   struct Log
   {
@@ -213,6 +214,7 @@ private:
     , Settings::Gui::WindowGeometry
     , Settings::Gui::ShowGenericClientFailureDialog
     , Settings::Gui::ShownFirstConnectedMessage
+    , Settings::Gui::ShownServerFirstStartMessage
     , Settings::Security::Certificate
     , Settings::Security::CheckPeers
     , Settings::Security::KeySize
@@ -225,6 +227,7 @@ private:
   inline static const QStringList m_defaultFalseValues = {
       Settings::Gui::Autohide
     , Settings::Gui::ShownFirstConnectedMessage
+    , Settings::Gui::ShownServerFirstStartMessage
     , Settings::Core::StartedBefore
     , Settings::Core::PreventSleep
     , Settings::Core::UseWlClipboard
diff --git a/src/lib/gui/MainWindow.cpp b/src/lib/gui/MainWindow.cpp
index 90d7515c4..3bbfeab0d 100644
--- a/src/lib/gui/MainWindow.cpp
+++ b/src/lib/gui/MainWindow.cpp
@@ -532,7 +532,6 @@ void MainWindow::updateModeControls(bool serverMode)
     // unrecognized client tries to connect.
     const auto startedBefore = Settings::value(Settings::Core::StartedBefore).toBool();
     if (!startedBefore && !m_coreProcess.isStarted()) {
-      qDebug() << "auto-starting core server for first time";
       m_coreProcess.start();
     }
   }
@@ -957,11 +956,14 @@ void MainWindow::coreProcessStateChanged(CoreProcessState state)
 {
   updateStatus();
 
-  if (state == CoreProcessState::Started && !Settings::value(Settings::Core::StartedBefore).toBool()) {
+  if (state == CoreProcessState::Started) {
     qDebug() << "recording that core has started";
     Settings::setValue(Settings::Core::StartedBefore, true);
-    if (m_coreProcess.mode() == CoreMode::Server) {
+    if (m_coreProcess.mode() == CoreMode::Server &&
+        !Settings::value(Settings::Gui::ShownServerFirstStartMessage).toBool()) {
+      qDebug() << "starting core server for first time";
       messages::showFirstServerStartMessage(this);
+      Settings::setValue(Settings::Gui::ShownServerFirstStartMessage, true);
     }
   }