diff --git a/doc/user/configuration.md b/doc/user/configuration.md
index 6350eb2f1..d175be43f 100644
--- a/doc/user/configuration.md
+++ b/doc/user/configuration.md
@@ -73,7 +73,6 @@ This section contains general options it will begin with `[core]`
 | preventSleep  | `true` or `false` | Prevent sleep when Deskflow is active [default: false] |
 | processMode   | `1` or `0`        | The mode we use to start the process Service or Desktop |
 | screenName    | string            | Name used to identify the screen [default: machine's hostname] |
-| startedBefore | `true` or `false `| Have we started client or server before. Used in logic when deciding to show some dialogs.
 | updateUrl     | URL               | The URL to use when checking for a new version number, it should return a version [default: https://api.deskflow.org/version]|
 | useHooks      | `true` or `false` | If Windows uses hooks or not [default: true] |
 | language      | 639 language      | The language to display the GUI in [default: en] |
@@ -106,6 +105,7 @@ This section contains options used by the GUI it will begin with `[gui]`
 | 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] |
+| startCoreWithGui               | `true` or `false` | When true the Core will be started with the GUI. It is set to the Core's state on exit. |
 
 ### Log
 
diff --git a/src/lib/common/Settings.h b/src/lib/common/Settings.h
index 4cfe8e601..ebcaec914 100644
--- a/src/lib/common/Settings.h
+++ b/src/lib/common/Settings.h
@@ -49,7 +49,6 @@ public:
     inline static const auto PreventSleep = QStringLiteral("core/preventSleep");
     inline static const auto ProcessMode = QStringLiteral("core/processMode");
     inline static const auto ScreenName = QStringLiteral("core/screenName");
-    inline static const auto StartedBefore = QStringLiteral("core/startedBefore");
     inline static const auto UpdateUrl = QStringLiteral("core/updateUrl");
     inline static const auto Display = QStringLiteral("core/display");
     inline static const auto UseHooks = QStringLiteral("core/useHooks");
@@ -66,6 +65,7 @@ public:
   struct Gui
   {
     inline static const auto Autohide = QStringLiteral("gui/autoHide");
+    inline static const auto AutoStartCore = QStringLiteral("gui/startCoreWithGui");
     inline static const auto AutoUpdateCheck = QStringLiteral("gui/enableUpdateCheck");
     inline static const auto CloseReminder = QStringLiteral("gui/closeReminder");
     inline static const auto CloseToTray = QStringLiteral("gui/closeToTray");
@@ -192,7 +192,6 @@ private:
     , Settings::Core::PreventSleep
     , Settings::Core::ProcessMode
     , Settings::Core::ScreenName
-    , Settings::Core::StartedBefore
     , Settings::Core::UpdateUrl
     , Settings::Core::Display
     , Settings::Core::UseHooks
@@ -206,6 +205,7 @@ private:
     , Settings::Log::ToFile
     , Settings::Log::GuiDebug
     , Settings::Gui::Autohide
+    , Settings::Gui::AutoStartCore
     , Settings::Gui::AutoUpdateCheck
     , Settings::Gui::CloseReminder
     , Settings::Gui::CloseToTray
@@ -226,9 +226,9 @@ private:
   // When checking the default values this list contains the ones that default to false.
   inline static const QStringList m_defaultFalseValues = {
       Settings::Gui::Autohide
+    , Settings::Gui::AutoStartCore
     , Settings::Gui::ShownFirstConnectedMessage
     , Settings::Gui::ShownServerFirstStartMessage
-    , Settings::Core::StartedBefore
     , Settings::Core::PreventSleep
     , Settings::Core::UseWlClipboard
     , Settings::Server::ExternalConfig
diff --git a/src/lib/gui/MainWindow.cpp b/src/lib/gui/MainWindow.cpp
index 3bbfeab0d..0030ad8cb 100644
--- a/src/lib/gui/MainWindow.cpp
+++ b/src/lib/gui/MainWindow.cpp
@@ -306,7 +306,12 @@ void MainWindow::connectSlots()
 
   connect(&m_clientConnection, &ClientConnection::requestShowError, this, &MainWindow::showClientError);
 
-  connect(ui->btnToggleCore, &QPushButton::clicked, m_actionStartCore, &QAction::trigger, Qt::UniqueConnection);
+  if (Settings::value(Settings::Gui::AutoStartCore).toBool()) {
+    connect(ui->btnToggleCore, &QPushButton::clicked, m_actionStopCore, &QAction::trigger, Qt::UniqueConnection);
+  } else {
+    connect(ui->btnToggleCore, &QPushButton::clicked, m_actionStartCore, &QAction::trigger, Qt::UniqueConnection);
+  }
+
   connect(ui->btnRestartCore, &QPushButton::clicked, this, &MainWindow::resetCore);
 
   connect(ui->lineHostname, &QLineEdit::returnPressed, ui->btnRestartCore, &QPushButton::click);
@@ -526,15 +531,6 @@ void MainWindow::updateModeControls(bool serverMode)
   if (m_coreProcess.isStarted() && m_coreProcess.mode() != expectedCoreMode)
     m_coreProcess.stop();
   m_coreProcess.setMode(expectedCoreMode);
-  if (serverMode) {
-    // The server can run without any clients configured, and this is actually
-    // what you'll want to do the first time since you'll be prompted when an
-    // unrecognized client tries to connect.
-    const auto startedBefore = Settings::value(Settings::Core::StartedBefore).toBool();
-    if (!startedBefore && !m_coreProcess.isStarted()) {
-      m_coreProcess.start();
-    }
-  }
   updateModeControlLabels();
 
   toggleCanRunCore((!serverMode && !ui->lineHostname->text().isEmpty()) || serverMode);
@@ -671,7 +667,7 @@ void MainWindow::open()
     qDebug() << "update check disabled";
   }
 
-  if (Settings::value(Settings::Core::StartedBefore).toBool()) {
+  if (Settings::value(Settings::Gui::AutoStartCore).toBool()) {
     if (ui->rbModeClient->isChecked() && ui->lineHostname->text().isEmpty())
       return;
     startCore();
@@ -867,6 +863,7 @@ void MainWindow::closeEvent(QCloseEvent *event)
 
   if (m_saveOnExit) {
     Settings::setValue(Settings::Gui::WindowGeometry, geometry());
+    Settings::setValue(Settings::Gui::AutoStartCore, m_coreProcess.isStarted());
   }
   qDebug() << "quitting application";
 
@@ -958,7 +955,7 @@ void MainWindow::coreProcessStateChanged(CoreProcessState state)
 
   if (state == CoreProcessState::Started) {
     qDebug() << "recording that core has started";
-    Settings::setValue(Settings::Core::StartedBefore, true);
+    Settings::setValue(Settings::Gui::AutoStartCore, true);
     if (m_coreProcess.mode() == CoreMode::Server &&
         !Settings::value(Settings::Gui::ShownServerFirstStartMessage).toBool()) {
       qDebug() << "starting core server for first time";