diff --git a/src/gui/src/MainWindow.cpp b/src/gui/src/MainWindow.cpp
index d32341ef..facff7e0 100644
--- a/src/gui/src/MainWindow.cpp
+++ b/src/gui/src/MainWindow.cpp
@@ -66,10 +66,11 @@ static const int debugLogLevel = 1;
 
 static const char* synergyIconFiles[] =
 {
-    ":/res/icons/16x16/synergy-disconnected.png",
-    ":/res/icons/16x16/synergy-disconnected.png",
-    ":/res/icons/16x16/synergy-connected.png",
-    ":/res/icons/16x16/synergy-transfering.png"
+    ":/res/icons/16x16/synergy-disconnected.png",   //synergyDisconnected
+    ":/res/icons/16x16/synergy-disconnected.png",   //synergyConnecting
+    ":/res/icons/16x16/synergy-connected.png",      //synergyConnected
+    ":/res/icons/16x16/synergy-transfering.png",    //synergyListening
+    ":/res/icons/16x16/synergy-disconnected.png"    //synergyPendingRetry
 };
 
 #ifdef SYNERGY_ENTERPRISE
@@ -442,7 +443,7 @@ void MainWindow::appendLogRaw(const QString& text)
 
 void MainWindow::updateFromLogLine(const QString &line)
 {
-    // TODO: this code makes Andrew cry
+    // TODO: This shouldn't be updating from log needs a better way of doing this
     checkConnected(line);
     checkFingerprint(line);
     checkSecureSocket(line);
@@ -712,6 +713,16 @@ void MainWindow::startSynergy()
     }
 }
 
+void MainWindow::retryStart()
+{
+    //This function is only called after a failed start
+    //Only start synergy if the current state is pending retry
+    if (m_SynergyState == synergyPendingRetry)
+    {
+        startSynergy();
+    }
+}
+
 void
 MainWindow::sslToggled (bool enabled)
 {
@@ -935,7 +946,9 @@ void MainWindow::synergyFinished(int exitCode, QProcess::ExitStatus)
     }
 
     if (m_ExpectedRunningState == kStarted) {
-        QTimer::singleShot(1000, this, SLOT(startSynergy()));
+
+        setSynergyState(synergyPendingRetry);
+        QTimer::singleShot(1000, this, SLOT(retryStart()));
         appendLogInfo(QString("detected process not running, auto restarting"));
     }
     else {
@@ -955,7 +968,7 @@ void MainWindow::setSynergyState(qSynergyState state)
     if (synergyState() == state)
         return;
 
-    if ((state == synergyConnected) || (state == synergyConnecting) || (state == synergyListening))
+    if ((state == synergyConnected) || (state == synergyConnecting) || (state == synergyListening) || (state == synergyPendingRetry))
     {
         disconnect (m_pButtonToggleStart, SIGNAL(clicked()), m_pActionStartSynergy, SLOT(trigger()));
         connect (m_pButtonToggleStart, SIGNAL(clicked()), m_pActionStopSynergy, SLOT(trigger()));
@@ -999,6 +1012,9 @@ void MainWindow::setSynergyState(qSynergyState state)
     case synergyConnecting:
         setStatus(tr("Synergy is starting..."));
         break;
+    case synergyPendingRetry:
+        setStatus(tr("There was an error, retrying..."));
+        break;
     case synergyDisconnected:
         setStatus(tr("Synergy is not running"));
         break;
diff --git a/src/gui/src/MainWindow.h b/src/gui/src/MainWindow.h
index e3308f3e..f4df8f4b 100644
--- a/src/gui/src/MainWindow.h
+++ b/src/gui/src/MainWindow.h
@@ -73,7 +73,8 @@ class MainWindow : public QMainWindow, public Ui::MainWindowBase
             synergyDisconnected,
             synergyConnecting,
             synergyConnected,
-            synergyListening
+            synergyListening,
+            synergyPendingRetry
         };
 
         enum qSynergyType
@@ -138,6 +139,7 @@ public slots:
         void appendLogDebug(const QString& text);
         void appendLogError(const QString& text);
         void startSynergy();
+        void retryStart(); // If the connection failed this will retry a startSynergy
 
     protected slots:
         void sslToggled(bool enabled);