diff --git a/spyder/plugins/updatemanager/widgets/update.py b/spyder/plugins/updatemanager/widgets/update.py
index 88c72896d8f..8fe722c6ccb 100644
--- a/spyder/plugins/updatemanager/widgets/update.py
+++ b/spyder/plugins/updatemanager/widgets/update.py
@@ -228,6 +228,7 @@ def _process_check_update(self):
         # Get results from worker
         update_available = self.update_worker.update_available
         error_msg = self.update_worker.error
+        checkbox = self.update_worker.checkbox
 
         # Always set status, regardless of error, DEV, or startup
         self.set_status(PENDING if update_available else NO_STATUS)
@@ -243,7 +244,7 @@ def _process_check_update(self):
             # Do not alert the user to anything
             pass
         elif error_msg is not None:
-            error_messagebox(self, error_msg)
+            error_messagebox(self, error_msg, checkbox)
         elif update_available:
             self.start_update()
         else:
@@ -532,10 +533,11 @@ def update_progress(self, progress, total):
         self._progress_bar.setValue(progress)
 
 
-def error_messagebox(parent, error_msg):
-    box = UpdateMessageBox(
-        icon=QMessageBox.Warning, text=error_msg, parent=parent
-    )
+def error_messagebox(parent, error_msg, checkbox=False):
+    # Use a message box with a checkbox to disable updates when required, or a
+    # standard one otherwise.
+    box_class = UpdateMessageCheckBox if checkbox else UpdateMessageBox
+    box = box_class(icon=QMessageBox.Warning, text=error_msg, parent=parent)
     box.setWindowTitle(_("Spyder update error"))
     box.setStandardButtons(QMessageBox.Ok)
     box.setDefaultButton(QMessageBox.Ok)
diff --git a/spyder/plugins/updatemanager/workers.py b/spyder/plugins/updatemanager/workers.py
index 5e372786438..8d008c2d6a1 100644
--- a/spyder/plugins/updatemanager/workers.py
+++ b/spyder/plugins/updatemanager/workers.py
@@ -51,6 +51,12 @@
     '<br><br>Please contact your network administrator for assistance.'
 )
 
+OS_ERROR_MSG = _(
+    "An error occurred while checking for Spyder updates, possibly related to "
+    "your operating system configuration or file access.<br><br>If you're not "
+    "sure what to do about it, you can disable checking for updates below. "
+    "<br><br>The error was:<br><br><i>{error}</i>"
+)
 
 def _rate_limits(page):
     """Log rate limits for GitHub.com"""
@@ -190,6 +196,7 @@ def __init__(self, stable_only):
         self.latest_release = None
         self.update_available = False
         self.error = None
+        self.checkbox = False
         self.channel = None
 
     def _check_update_available(
@@ -294,6 +301,10 @@ def start(self):
         except HTTPError as err:
             error_msg = HTTP_ERROR_MSG.format(status_code=page.status_code)
             logger.warning(err, exc_info=err)
+        except OSError as err:
+            error_msg = OS_ERROR_MSG.format(error=err)
+            self.checkbox = True
+            logger.warning(err, exc_info=err)
         except Exception as err:
             # Send untracked errors to our error reporter
             error_data = dict(