diff --git a/src/lib/gui/MainWindow.cpp b/src/lib/gui/MainWindow.cpp
index 7c510d628..7dd810a36 100644
--- a/src/lib/gui/MainWindow.cpp
+++ b/src/lib/gui/MainWindow.cpp
@@ -289,6 +289,7 @@ void MainWindow::connectSlots()
   connect(&m_coreProcess, &CoreProcess::processStateChanged, this, &MainWindow::coreProcessStateChanged);
   connect(&m_coreProcess, &CoreProcess::connectionStateChanged, this, &MainWindow::coreConnectionStateChanged);
   connect(&m_coreProcess, &CoreProcess::secureSocket, this, &MainWindow::secureSocket);
+  connect(&m_coreProcess, &CoreProcess::daemonIpcClientConnectFailed, this, &MainWindow::daemonIpcClientConnectFailed);
 
   connect(m_actionAbout, &QAction::triggered, this, &MainWindow::openAboutDialog);
   connect(m_actionClearSettings, &QAction::triggered, this, &MainWindow::clearSettings);
@@ -365,6 +366,21 @@ void MainWindow::firstShown()
   // hacky and fragile, so maybe there's a better approach.
   const auto kCriticalDialogDelay = 100;
   QTimer::singleShot(kCriticalDialogDelay, this, &messages::raiseCriticalDialog);
+
+  if (!Settings::value(Settings::Gui::AutoUpdateCheck).isValid()) {
+    showAndActivate();
+    Settings::setValue(Settings::Gui::AutoUpdateCheck, messages::showUpdateCheckOption(this));
+  }
+
+  if (Settings::value(Settings::Gui::AutoUpdateCheck).toBool()) {
+    m_versionChecker.checkLatest();
+  } else {
+    qDebug() << "update check disabled";
+  }
+
+  if (Settings::value(Settings::Core::StartedBefore).toBool()) {
+    m_coreProcess.start();
+  }
 }
 
 void MainWindow::settingsChanged(const QString &key)
@@ -603,24 +619,6 @@ void MainWindow::serverConnectionConfigureClient(const QString &clientName)
 
 void MainWindow::open()
 {
-
-  if (!Settings::value(Settings::Gui::AutoUpdateCheck).isValid()) {
-    showAndActivate();
-    Settings::setValue(Settings::Gui::AutoUpdateCheck, messages::showUpdateCheckOption(this));
-  }
-
-  if (Settings::value(Settings::Gui::AutoUpdateCheck).toBool()) {
-    m_versionChecker.checkLatest();
-  } else {
-    qDebug() << "update check disabled";
-  }
-
-  m_coreProcess.applyLogLevel();
-
-  if (Settings::value(Settings::Core::StartedBefore).toBool()) {
-    m_coreProcess.start();
-  }
-
   Settings::value(Settings::Gui::Autohide).toBool() ? hide() : showAndActivate();
 }
 
@@ -1137,3 +1135,10 @@ bool MainWindow::regenerateLocalFingerprints()
   updateLocalFingerprint();
   return true;
 }
+
+void MainWindow::daemonIpcClientConnectFailed()
+{
+  if (deskflow::gui::messages::showDaemonOffline(this)) {
+    m_coreProcess.retryDaemon();
+  }
+}
diff --git a/src/lib/gui/MainWindow.h b/src/lib/gui/MainWindow.h
index ab828e5be..61b66f6af 100644
--- a/src/lib/gui/MainWindow.h
+++ b/src/lib/gui/MainWindow.h
@@ -158,6 +158,7 @@ private:
   void showAndActivate();
   void showHostNameEditor();
   void setHostName();
+  void daemonIpcClientConnectFailed();
 
   /**
    * @brief trustedFingerprintDb get the fingerprintDb for the trusted clients or trusted servers.
diff --git a/src/lib/gui/Messages.cpp b/src/lib/gui/Messages.cpp
index e55b6e944..32ad9c028 100644
--- a/src/lib/gui/Messages.cpp
+++ b/src/lib/gui/Messages.cpp
@@ -309,4 +309,35 @@ bool showUpdateCheckOption(QWidget *parent)
   return message.clickedButton() == checkButton;
 }
 
+bool showDaemonOffline(QWidget *parent)
+{
+  QMessageBox message(parent);
+  message.setIcon(QMessageBox::Warning);
+  message.setWindowTitle(QObject::tr("Background service offline"));
+
+  message.addButton(QObject::tr("Retry"), QMessageBox::AcceptRole);
+  const auto ignore = message.addButton(QObject::tr("Ignore"), QMessageBox::RejectRole);
+  const auto disable = message.addButton(QObject::tr("Disable"), QMessageBox::NoRole);
+
+  message.setText(QString(
+                      "<p>There was a problem finding the %1 background service (daemon).</p>"
+                      "<p>The background service makes %1 work with UAC prompts and the login screen.</p>"
+                      "<p>If don't want to use the background service and intentionally stopped it, "
+                      "you can prevent it's use by disabling this feature.</p>"
+                      "<p>If you did not stop the background service intentionally, there may be a problem with it. "
+                      "Please retry or try restarting the %1 service from the Windows services program.</p>"
+  )
+                      .arg(kAppName));
+  message.exec();
+
+  if (message.clickedButton() == ignore) {
+    return false;
+  } else if (message.clickedButton() == disable) {
+    Settings::setValue(Settings::Core::ProcessMode, Settings::ProcessMode::Desktop);
+    return false;
+  }
+
+  return true;
+}
+
 } // namespace deskflow::gui::messages
diff --git a/src/lib/gui/Messages.h b/src/lib/gui/Messages.h
index 1f1eb8df1..f035e2092 100644
--- a/src/lib/gui/Messages.h
+++ b/src/lib/gui/Messages.h
@@ -49,4 +49,6 @@ void showWaylandLibraryError(QWidget *parent);
 
 bool showUpdateCheckOption(QWidget *parent);
 
+bool showDaemonOffline(QWidget *parent);
+
 } // namespace deskflow::gui::messages
diff --git a/src/lib/gui/core/CoreProcess.cpp b/src/lib/gui/core/CoreProcess.cpp
index 63acf8cb2..cf0e221d5 100644
--- a/src/lib/gui/core/CoreProcess.cpp
+++ b/src/lib/gui/core/CoreProcess.cpp
@@ -140,6 +140,7 @@ CoreProcess::CoreProcess(const IServerConfig &serverConfig, std::shared_ptr<Deps
       m_daemonIpcClient{new ipc::DaemonIpcClient(this)}
 {
   connect(m_daemonIpcClient, &ipc::DaemonIpcClient::connected, this, &CoreProcess::daemonIpcClientConnected);
+  connect(m_daemonIpcClient, &ipc::DaemonIpcClient::connectFailed, this, &CoreProcess::daemonIpcClientConnectFailed);
 
   connect(&m_pDeps->process(), &QProcessProxy::finished, this, &CoreProcess::onProcessFinished);
 
@@ -224,7 +225,7 @@ void CoreProcess::applyLogLevel()
   if (processMode == ProcessMode::Service) {
     qDebug() << "setting daemon log level:" << Settings::logLevelText();
     if (!m_daemonIpcClient->sendLogLevel(Settings::logLevelText())) {
-      qCritical() << "failed to set daemon ipc log level";
+      qWarning() << "failed to set daemon ipc log level";
     }
   }
 }
@@ -263,7 +264,7 @@ void CoreProcess::startProcessFromDaemon(const QString &app, const QStringList &
   qInfo("running command: %s", qPrintable(commandQuoted));
 
   if (!m_daemonIpcClient->sendStartProcess(commandQuoted, Settings::value(Settings::Daemon::Elevate).toBool())) {
-    qCritical("cannot start process, ipc command failed");
+    qWarning("cannot start process, ipc command failed");
     return;
   }
 
@@ -297,7 +298,7 @@ void CoreProcess::stopProcessFromDaemon()
   }
 
   if (!m_daemonIpcClient->sendStopProcess()) {
-    qCritical("cannot stop process, ipc command failed");
+    qWarning("cannot stop process, ipc command failed");
     return;
   }
 
@@ -736,4 +737,11 @@ void CoreProcess::clearSettings()
   m_daemonIpcClient->sendClearSettings();
 }
 
+void CoreProcess::retryDaemon()
+{
+  if (m_daemonIpcClient->connectToServer()) {
+    qInfo("successfully reconnected to daemon");
+  }
+}
+
 } // namespace deskflow::gui
diff --git a/src/lib/gui/core/CoreProcess.h b/src/lib/gui/core/CoreProcess.h
index fba64a684..03b0ed110 100644
--- a/src/lib/gui/core/CoreProcess.h
+++ b/src/lib/gui/core/CoreProcess.h
@@ -79,6 +79,7 @@ public:
   void cleanup();
   void applyLogLevel();
   void clearSettings();
+  void retryDaemon();
 
   // getters
   Settings::CoreMode mode() const
@@ -119,6 +120,7 @@ signals:
   void connectionStateChanged(ConnectionState state);
   void processStateChanged(ProcessState state);
   void secureSocket(bool enabled);
+  void daemonIpcClientConnectFailed();
 
 private slots:
   void onProcessFinished(int exitCode, QProcess::ExitStatus);
diff --git a/src/lib/gui/ipc/DaemonIpcClient.cpp b/src/lib/gui/ipc/DaemonIpcClient.cpp
index 12d1930e8..20b570620 100644
--- a/src/lib/gui/ipc/DaemonIpcClient.cpp
+++ b/src/lib/gui/ipc/DaemonIpcClient.cpp
@@ -27,20 +27,32 @@ DaemonIpcClient::DaemonIpcClient(QObject *parent)
 
 bool DaemonIpcClient::connectToServer()
 {
-  qDebug() << "daemon ipc client connecting to server:" << kDaemonIpcName;
+  if (m_connecting) {
+    qDebug() << "daemon ipc client already connecting to server";
+    return false;
+  }
 
+  qDebug() << "daemon ipc client connecting to server:" << kDaemonIpcName;
+  m_connecting = true;
   m_socket->connectToServer(kDaemonIpcName);
+
   if (!m_socket->waitForConnected(kTimeout)) {
     qWarning() << "daemon ipc client failed to connect";
+    m_connecting = false;
+    Q_EMIT connectFailed();
     return false;
   }
 
   if (!sendMessage("hello", "hello", false)) {
     qWarning() << "daemon ipc client failed to send hello";
+    m_connecting = false;
+    Q_EMIT connectFailed();
     return false;
   }
 
+  m_connecting = false;
   m_connected = true;
+
   qDebug() << "daemon ipc client connected";
   Q_EMIT connected();
 
@@ -51,10 +63,7 @@ void DaemonIpcClient::handleDisconnected()
 {
   qWarning() << "daemon ipc client disconnected from server";
   m_connected = false;
-
-  if (!connectToServer()) {
-    qWarning() << "daemon ipc client failed to reconnect to server";
-  }
+  Q_EMIT connectFailed();
 }
 
 void DaemonIpcClient::handleErrorOccurred()
diff --git a/src/lib/gui/ipc/DaemonIpcClient.h b/src/lib/gui/ipc/DaemonIpcClient.h
index df694d528..6b52b9d47 100644
--- a/src/lib/gui/ipc/DaemonIpcClient.h
+++ b/src/lib/gui/ipc/DaemonIpcClient.h
@@ -8,8 +8,6 @@
 
 #include <QObject>
 
-#include "common/Settings.h"
-
 class QLocalSocket;
 
 namespace deskflow::gui::ipc {
@@ -34,6 +32,7 @@ public:
 
 signals:
   void connected();
+  void connectFailed();
 
 private slots:
   void handleDisconnected();
@@ -46,6 +45,7 @@ private:
 private:
   QLocalSocket *m_socket;
   bool m_connected{false};
+  bool m_connecting{false};
 };
 
 } // namespace deskflow::gui::ipc