diff --git a/src/calibre/devices/interface.py b/src/calibre/devices/interface.py
index 913c686f2e..0cc814d2ec 100644
--- a/src/calibre/devices/interface.py
+++ b/src/calibre/devices/interface.py
@@ -10,10 +10,11 @@ from calibre.customize import Plugin
 
 class OpenPopupMessage:
 
-    def __init__(self, title='', message='', level='info'):
+    def __init__(self, title='', message='', level='info', skip_dialog_skip_precheck=True):
         self.title = title
         self.message = message
         self.level = level
+        self.skip_dialog_skip_precheck = skip_dialog_skip_precheck
 
 
 class DevicePlugin(Plugin):
diff --git a/src/calibre/gui2/device.py b/src/calibre/gui2/device.py
index ff9b92de0a..5b2ddbc9da 100644
--- a/src/calibre/gui2/device.py
+++ b/src/calibre/gui2/device.py
@@ -155,7 +155,7 @@ def convert_open_popup(opm, skip_key):
             tc = m.toggle_checkbox
             tc.setVisible(True)
             tc.setText(_('Show this message again'))
-            tc.setChecked(True)
+            tc.setChecked(not self.opm.skip_dialog_skip_precheck)
             m.resize_needed.emit()
             m.finished.connect(m.on_cd_finished)
             return m