diff --git a/src/calibre/devices/interface.py b/src/calibre/devices/interface.py
index f0c917d475..913c686f2e 100644
--- a/src/calibre/devices/interface.py
+++ b/src/calibre/devices/interface.py
@@ -8,6 +8,14 @@ from calibre.constants import iswindows
 from calibre.customize import Plugin
 
 
+class OpenPopupMessage:
+
+    def __init__(self, title='', message='', level='info'):
+        self.title = title
+        self.message = message
+        self.level = level
+
+
 class DevicePlugin(Plugin):
     """
     Defines the interface that should be implemented by backends that
@@ -69,7 +77,7 @@ class DevicePlugin(Plugin):
     # Encapsulates an annotation fetched from the device
     UserAnnotation = namedtuple('Annotation','type, value')
 
-    #: GUI displays this as a message if not None. Useful if opening can take a
+    #: GUI displays this as a message if not None in the status bar. Useful if opening can take a
     #: long time
     OPEN_FEEDBACK_MESSAGE = None
 
@@ -126,6 +134,11 @@ class DevicePlugin(Plugin):
             return cls.__name__
         return cls.name
 
+    @classmethod
+    def get_open_popup_message(self):
+        ' GUI displays this as a non-modal popup. Should be an instance of OpenPopupMessage '
+        return None
+
     # Device detection {{{
     def test_bcd(self, bcdDevice, bcd):
         if bcd is None or len(bcd) == 0:
diff --git a/src/calibre/devices/kindle/driver.py b/src/calibre/devices/kindle/driver.py
index fe9e4f411f..65d69463e9 100644
--- a/src/calibre/devices/kindle/driver.py
+++ b/src/calibre/devices/kindle/driver.py
@@ -9,6 +9,7 @@ Device driver for Amazon's Kindle
 import datetime, os, re, json, hashlib, errno
 
 from calibre.constants import DEBUG, filesystem_encoding
+from calibre.devices.interface import OpenPopupMessage
 from calibre.devices.kindle.bookmark import Bookmark
 from calibre.devices.usbms.driver import USBMS
 from calibre import strftime, fsync, prints
@@ -95,6 +96,18 @@ class KINDLE(USBMS):
         ' Click "Show details" to see the list of books.'
     )
 
+    @classmethod
+    def get_open_popup_message(cls):
+        from calibre.utils.localization import localize_website_link
+        return OpenPopupMessage(title=_('WARNING: E-book covers'), message=_(
+            'Amazon has <b>broken display of covers</b> for books sent to the Kindle by USB cable. To workaround it,'
+            ' you have to: <ol><li>Send the books to the Kindle</li><li>Disconnect the Kindle and wait for the covers to be deleted'
+            ' by Amazon</li><li>Reconnect the Kindle and calibre will restore the covers.</li></ol> After this the'
+            ' covers for those books should stay put. <a href="{}">Click here</a> for details.').format(localize_website_link(
+                'https://manual.calibre-ebook.com/faq.html#covers-for-books-i'
+                '-send-to-my-e-ink-kindle-show-up-momentarily-and-then-are-replaced-by-a-generic-cover')
+        ))
+
     def is_allowed_book_file(self, filename, path, prefix):
         lpath = os.path.join(path, filename).partition(self.normalize_path(prefix))[2].replace('\\', '/')
         return '.sdr/' not in lpath
diff --git a/src/calibre/gui2/device.py b/src/calibre/gui2/device.py
index b0f82747b6..ff9b92de0a 100644
--- a/src/calibre/gui2/device.py
+++ b/src/calibre/gui2/device.py
@@ -132,6 +132,37 @@ class BusyCursor:
         QApplication.restoreOverrideCursor()
 
 
+def convert_open_popup(opm, skip_key):
+    class OPM(OpenFeedback):
+
+        def __init__(self, opm):
+            super().__init__('placeholder')
+            self.opm = opm
+            self.skip_key = skip_key
+
+        def custom_dialog(self, parent):
+            from calibre.gui2.dialogs.message_box import MessageBox
+
+            class M(MessageBox):
+                def on_cd_finished(s):
+                    gprefs.set(self.skip_key, not s.toggle_checkbox.isChecked())
+            m = M({
+                'info': MessageBox.INFO, 'information': MessageBox.INFO,
+                'warn': MessageBox.WARNING, 'warning': MessageBox.WARNING,
+                }[self.opm.level], self.opm.title, self.opm.message,
+                parent=parent
+            )
+            tc = m.toggle_checkbox
+            tc.setVisible(True)
+            tc.setText(_('Show this message again'))
+            tc.setChecked(True)
+            m.resize_needed.emit()
+            m.finished.connect(m.on_cd_finished)
+            return m
+
+    return OPM(opm)
+
+
 class DeviceManager(Thread):  # {{{
 
     def __init__(self, connected_slot, job_manager, open_feedback_slot,
@@ -191,6 +222,11 @@ class DeviceManager(Thread):  # {{{
         for dev, detected_device in connected_devices:
             if dev.OPEN_FEEDBACK_MESSAGE is not None:
                 self.open_feedback_slot(dev.OPEN_FEEDBACK_MESSAGE)
+            opm = dev.get_open_popup_message()
+            if opm is not None:
+                skip_key = f'do_not_show_device_open_popup_message_{dev.__class__.__name__}'
+                if not gprefs.get(skip_key, False):
+                    self.open_feedback_msg(dev.get_gui_name(), convert_open_popup(opm, skip_key))
             try:
                 dev.reset(detected_device=detected_device,
                     report_progress=self.report_progress)