diff --git a/src/calibre/gui2/dialogs/smartdevice.py b/src/calibre/gui2/dialogs/smartdevice.py
index b83db2bd18..1a8829323b 100644
--- a/src/calibre/gui2/dialogs/smartdevice.py
+++ b/src/calibre/gui2/dialogs/smartdevice.py
@@ -53,11 +53,13 @@ class SmartdeviceDialog(QDialog, Ui_Dialog):
         if pw:
             self.password_box.setText(pw)
 
-        use_fixed_port = self.device_manager.get_option('smartdevice', 'use_fixed_port')
-        port_number = self.device_manager.get_option('smartdevice', 'port_number')
-        self.fixed_port.setText(port_number)
-        self.use_fixed_port.setChecked(use_fixed_port);
-        if not use_fixed_port:
+        self.orig_fixed_port = self.device_manager.get_option('smartdevice',
+                                                             'use_fixed_port')
+        self.orig_port_number = self.device_manager.get_option('smartdevice',
+                                                          'port_number')
+        self.fixed_port.setText(self.orig_port_number)
+        self.use_fixed_port.setChecked(self.orig_fixed_port);
+        if not self.orig_fixed_port:
             self.fixed_port.setEnabled(False);
 
         if pw:
@@ -85,8 +87,13 @@ class SmartdeviceDialog(QDialog, Ui_Dialog):
         message = self.device_manager.start_plugin('smartdevice')
 
         if not self.device_manager.is_running('smartdevice'):
-            error_dialog(self, _('Problem starting smartdevice'),
-                _('The snart device driver did not start. It said "%s"')%message, show=True)
+            error_dialog(self, _('Problem starting the wireless device'),
+                _('The wireless device driver did not start. It said "%s"')%message,
+                show=True)
+            self.device_manager.set_option('smartdevice', 'use_fixed_port',
+                                           self.orig_fixed_port)
+            self.device_manager.set_option('smartdevice', 'port_number',
+                                           self.orig_port_number)
         else:
             QDialog.accept(self)
 
diff --git a/src/calibre/gui2/ui.py b/src/calibre/gui2/ui.py
index 67415bee9e..2271c82c4f 100644
--- a/src/calibre/gui2/ui.py
+++ b/src/calibre/gui2/ui.py
@@ -339,14 +339,6 @@ class Main(MainWindow, MainWindowMixin, DeviceMixin, EmailMixin, # {{{
         if config['autolaunch_server']:
             self.start_content_server()
 
-        smartdevice_action = self.iactions['Connect Share']
-        smartdevice_action.check_smartdevice_menus()
-        if self.device_manager.get_option('smartdevice', 'autostart'):
-            try:
-                self.device_manager.start_plugin('smartdevice')
-            except:
-                pass
-        smartdevice_action.set_smartdevice_action_state()
 
         self.keyboard_interrupt.connect(self.quit, type=Qt.QueuedConnection)
 
@@ -381,9 +373,29 @@ class Main(MainWindow, MainWindowMixin, DeviceMixin, EmailMixin, # {{{
                         'the file: %s<p>The '
                         'log will be displayed automatically.')%self.gui_debug, show=True)
 
+        self.iactions['Connect Share'].check_smartdevice_menus()
+        QTimer.singleShot(1, self.start_smartdevice)
+
     def esc(self, *args):
         self.clear_button.click()
 
+    def start_smartdevice(self):
+        message = None
+        if self.device_manager.get_option('smartdevice', 'autostart'):
+            try:
+                message = self.device_manager.start_plugin('smartdevice')
+            except:
+                message = 'start smartdevice unknown exception'
+                prints(message)
+                import traceback
+                traceback.print_exc()
+        if message:
+            if not self.device_manager.is_running('Wireless Devices'):
+                    error_dialog(self, _('Problem starting the wireless device'),
+                                 _('The wireless device driver did not start. '
+                                   'It said "%s"')%message,  show=True)
+        self.iactions['Connect Share'].set_smartdevice_action_state()
+
     def start_content_server(self, check_started=True):
         from calibre.library.server.main import start_threaded_server
         from calibre.library.server import server_config