diff --git a/main.c b/main.c
index 6b7f44e..c1ee3d5 100644
--- a/main.c
+++ b/main.c
@@ -188,6 +188,7 @@ int WINAPI _tWinMain (HINSTANCE hThisInstance,
       { echo_,     OnEcho },
       { bytecount_,OnByteCount },
       { infomsg_,  OnInfoMsg },
+      { timeout_,  OnTimeout },
       { 0,        NULL }
   };
   InitManagement(handler);
diff --git a/manage.c b/manage.c
index cfd96f9..a567af7 100644
--- a/manage.c
+++ b/manage.c
@@ -209,10 +209,9 @@ OnManagement(SOCKET sk, LPARAM lParam)
             else
             {
                 /* Connection to MI timed out. */
-                if (c->state != disconnected)
-                    c->state = timedout;
                 CloseManagement (c);
-                rtmsg_handler[stop_](c, "");
+                if (c->state != disconnected)
+                    rtmsg_handler[timeout_](c, "");
             }
         }
         else
diff --git a/manage.h b/manage.h
index 7b7f005..7c9dba4 100644
--- a/manage.h
+++ b/manage.h
@@ -38,6 +38,7 @@ typedef enum {
     needstr_,
     pkcs11_id_count_,
     infomsg_,
+    timeout_,
     mgmt_rtmsg_type_max
 } mgmt_rtmsg_type;
 
diff --git a/openvpn.c b/openvpn.c
index 81d457d..b5974d6 100644
--- a/openvpn.c
+++ b/openvpn.c
@@ -1231,6 +1231,32 @@ OnPassword(connection_t *c, char *msg)
     }
 }
 
+/*
+ * Handle management connection timeout
+ */
+void
+OnTimeout(connection_t *c, UNUSED char *msg)
+{
+    /* Connection to management timed out -- keep trying unless killed
+     * by a startup error from service or from openvpn daemon process.
+     * The user can terminate by pressing disconnect.
+     */
+    if (o.silent_connection == 0)
+    {
+        SetForegroundWindow(c->hwndStatus);
+        ShowWindow(c->hwndStatus, SW_SHOW);
+    }
+    WriteStatusLog (c, L"GUI> ", LoadLocalizedString(IDS_NFO_CONN_TIMEOUT, c->log_path), false);
+    WriteStatusLog (c, L"GUI> ", L"Retrying. Press disconnect to abort", false);
+    c->state = connecting;
+    if (!OpenManagement(c))
+    {
+        MessageBoxEx(NULL, L"Failed to open management", _T(PACKAGE_NAME),
+                     MB_OK|MB_SETFOREGROUND|MB_ICONERROR, GetGUILanguage());
+        StopOpenVPN(c);
+    }
+    return;
+}
 
 /*
  * Handle exit of the OpenVPN process
@@ -1239,7 +1265,6 @@ void
 OnStop(connection_t *c, UNUSED char *msg)
 {
     UINT txt_id, msg_id;
-    TCHAR *msg_xtra;
     SetMenuStatus(c, disconnected);
 
     switch (c->state)
@@ -1267,13 +1292,9 @@ OnStop(connection_t *c, UNUSED char *msg)
     case resuming:
     case connecting:
     case reconnecting:
-    case timedout:
         /* We have failed to (re)connect */
         txt_id = c->state == reconnecting ? IDS_NFO_STATE_FAILED_RECONN : IDS_NFO_STATE_FAILED;
         msg_id = c->state == reconnecting ? IDS_NFO_RECONN_FAILED : IDS_NFO_CONN_FAILED;
-        msg_xtra = c->state == timedout ? c->log_path : c->config_name;
-        if (c->state == timedout)
-            msg_id = IDS_NFO_CONN_TIMEOUT;
 
         c->state = disconnecting;
         CheckAndSetTrayIcon();
@@ -1287,7 +1308,7 @@ OnStop(connection_t *c, UNUSED char *msg)
             SetForegroundWindow(c->hwndStatus);
             ShowWindow(c->hwndStatus, SW_SHOW);
         }
-        MessageBox(c->hwndStatus, LoadLocalizedString(msg_id, msg_xtra), _T(PACKAGE_NAME), MB_OK);
+        MessageBox(c->hwndStatus, LoadLocalizedString(msg_id, c->config_name), _T(PACKAGE_NAME), MB_OK);
         SendMessage(c->hwndStatus, WM_CLOSE, 0, 0);
         break;
 
@@ -1649,12 +1670,10 @@ OnService(connection_t *c, UNUSED char *msg)
             break;
         case ERROR_STARTUP_DATA:
             WriteStatusLog (c, prefix, L"OpenVPN not started due to previous errors", true);
-            c->state = timedout;   /* Force the popup message to include the log file name */
             OnStop (c, NULL);
             break;
         case ERROR_OPENVPN_STARTUP:
             WriteStatusLog (c, prefix, L"Check the log file for details", false);
-            c->state = timedout;   /* Force the popup message to include the log file name */
             OnStop(c, NULL);
             break;
         default:
@@ -1992,7 +2011,11 @@ ThreadOpenVPNStatus(void *p)
     SetWindowText(c->hwndStatus, LoadLocalizedString(IDS_NFO_CONNECTION_XXX, conn_name));
 
     if (!OpenManagement(c))
-        PostMessage(c->hwndStatus, WM_CLOSE, 0, 0);
+    {
+        MessageBoxEx(NULL, L"Failed to open management", _T(PACKAGE_NAME),
+                     MB_OK|MB_SETFOREGROUND|MB_ICONERROR, GetGUILanguage());
+        StopOpenVPN(c);
+    }
 
     /* Start the async read loop for service and set it as the wait event */
     if (c->iserv.hEvent)
diff --git a/openvpn.h b/openvpn.h
index 18ef250..8222a7e 100644
--- a/openvpn.h
+++ b/openvpn.h
@@ -43,6 +43,7 @@ void OnNeedStr(connection_t *, char *);
 void OnEcho(connection_t *, char *);
 void OnByteCount(connection_t *, char *);
 void OnInfoMsg(connection_t*, char*);
+void OnTimeout(connection_t *, char *);
 
 void ResetSavePasswords(connection_t *);
 
diff --git a/options.h b/options.h
index 3a93ffb..b31ff4d 100644
--- a/options.h
+++ b/options.h
@@ -71,7 +71,6 @@ typedef enum {
     suspending,
     suspended,
     resuming,
-    timedout
 } conn_state_t;
 
 /* Interactive Service IO parameters */