diff --git a/src/calibre/devices/usbms/driver.py b/src/calibre/devices/usbms/driver.py
index dde84a97c9..182ded099f 100644
--- a/src/calibre/devices/usbms/driver.py
+++ b/src/calibre/devices/usbms/driver.py
@@ -14,7 +14,7 @@ for a particular device.
 import os, time, json, shutil
 from itertools import cycle
 
-from calibre.constants import numeric_version
+from calibre.constants import numeric_version, ismacos
 from calibre import prints, isbytestring, fsync
 from calibre.constants import filesystem_encoding, DEBUG
 from calibre.devices.usbms.cli import CLI
@@ -147,17 +147,30 @@ class USBMS(CLI, Device):
     def get_device_information(self, end_session=True):
         self.report_progress(1.0, _('Get device information...'))
         self.driveinfo = {}
+
+        def raise_os_error(e):
+            raise OSError(_('Failed to access files in the main memory of'
+                    ' your device. You should contact the device'
+                    ' manufacturer for support. Common fixes are:'
+                    ' try a different USB cable/USB port on your computer.'
+                    ' If you device has a "Reset to factory defaults" type'
+                    ' of setting somewhere, use it. Underlying error: %s')
+                    % e) from e
+
         if self._main_prefix is not None:
             try:
                 self.driveinfo['main'] = self._update_driveinfo_file(self._main_prefix, 'main')
+            except PermissionError as e:
+                if ismacos:
+                    raise PermissionError(_(
+                        'Permission was denied by macOS trying to access files in the main memory of'
+                        ' your device. You will need to grant permission explicitly by looking under'
+                        ' System Preferences > Security and Privacy > Privacy > Files and Folders.'
+                        ' Underlying error: %s'
+                    ) % e) from e
+                raise_os_error(e)
             except OSError as e:
-                raise OSError(_('Failed to access files in the main memory of'
-                        ' your device. You should contact the device'
-                        ' manufacturer for support. Common fixes are:'
-                        ' try a different USB cable/USB port on your computer.'
-                        ' If you device has a "Reset to factory defaults" type'
-                        ' of setting somewhere, use it. Underlying error: %s')
-                        % e)
+                raise_os_error(e)
         try:
             if self._card_a_prefix is not None:
                 self.driveinfo['A'] = self._update_driveinfo_file(self._card_a_prefix, 'A')