diff --git a/onionshare_gui/onionshare_gui.py b/onionshare_gui/onionshare_gui.py
index e1d07ada..bdf0d105 100644
--- a/onionshare_gui/onionshare_gui.py
+++ b/onionshare_gui/onionshare_gui.py
@@ -384,24 +384,17 @@ class OnionShareGui(QtWidgets.QMainWindow):
         Check for messages communicated from the web app, and update the GUI accordingly.
         """
         self.update()
-
-        # If the auto-shutdown timer has stopped, stop the server
-        if self.server_status.status == self.server_status.STATUS_STARTED:
-            if self.app.shutdown_timer and self.server_status.timer_enabled:
-                if self.timeout > 0:
-                    if not self.app.shutdown_timer.is_alive():
-                        self.server_status.stop_server()
-                        self.status_bar.showMessage(strings._('close_on_timeout',True))
-                        self.server_status.shutdown_timeout_reset()
+        global download_in_progress
+        try:
+           download_in_progress
+        except NameError:
+           download_in_progress = False
 
         # scroll to the bottom of the dl progress bar log pane
         # if a new download has been added
         if self.new_download:
             self.vbar.setValue(self.vbar.maximum())
             self.new_download = False
-        # only check for requests if the server is running
-        if self.server_status.status != self.server_status.STATUS_STARTED:
-            return
 
         events = []
 
@@ -430,9 +423,11 @@ class OnionShareGui(QtWidgets.QMainWindow):
 
             elif event["type"] == web.REQUEST_PROGRESS:
                 self.downloads.update_download(event["data"]["id"], event["data"]["bytes"])
+                download_in_progress = True
 
                 # is the download complete?
                 if event["data"]["bytes"] == web.zip_filesize:
+                    download_in_progress = False
                     if self.systemTray.supportsMessages() and self.settings.get('systray_notifications'):
                         self.systemTray.showMessage(strings._('systray_download_completed_title', True), strings._('systray_download_completed_message', True))
                     # close on finish?
@@ -441,6 +436,7 @@ class OnionShareGui(QtWidgets.QMainWindow):
                         self.server_status.shutdown_timeout_reset()
 
             elif event["type"] == web.REQUEST_CANCELED:
+                download_in_progress = False
                 self.downloads.cancel_download(event["data"]["id"])
                 if self.systemTray.supportsMessages() and self.settings.get('systray_notifications'):
                     self.systemTray.showMessage(strings._('systray_download_canceled_title', True), strings._('systray_download_canceled_message', True))
@@ -448,6 +444,18 @@ class OnionShareGui(QtWidgets.QMainWindow):
             elif event["path"] != '/favicon.ico':
                 self.status_bar.showMessage('[#{0:d}] {1:s}: {2:s}'.format(web.error404_count, strings._('other_page_loaded', True), event["path"]))
 
+        # If the auto-shutdown timer has stopped, stop the server
+        if self.server_status.status == self.server_status.STATUS_STARTED:
+            if self.app.shutdown_timer and self.server_status.timer_enabled:
+                if self.timeout > 0:
+                    if not self.app.shutdown_timer.is_alive():
+                        if not download_in_progress:
+                            self.server_status.stop_server()
+                            self.status_bar.showMessage(strings._('close_on_timeout',True))
+                            self.server_status.shutdown_timeout_reset()
+                        else:
+                            self.status_bar.showMessage(strings._('timeout_download_still_running', True))
+
     def copy_url(self):
         """
         When the URL gets copied to the clipboard, display this in the status bar.
diff --git a/share/locale/en.json b/share/locale/en.json
index 2847d33d..03a6a28e 100644
--- a/share/locale/en.json
+++ b/share/locale/en.json
@@ -14,6 +14,7 @@
     "other_page_loaded": "URL loaded",
     "close_on_timeout": "Closing automatically because timeout was reached",
     "closing_automatically": "Closing automatically because download finished",
+    "timeout_download_still_running": "Waiting for download to complete before auto-stopping",
     "large_filesize": "Warning: Sending large files could take hours",
     "error_tails_invalid_port": "Invalid value, port must be an integer",
     "error_tails_unknown_root": "Unknown error with Tails root process",