diff --git a/onionshare_gui/server_status.py b/onionshare_gui/server_status.py
index 4bd9241b..3ee10f14 100644
--- a/onionshare_gui/server_status.py
+++ b/onionshare_gui/server_status.py
@@ -312,11 +312,16 @@ class ServerStatus(QtWidgets.QWidget):
         Toggle starting or stopping the server.
         """
         if self.status == self.STATUS_STOPPED:
+            can_start = True
             if self.common.settings.get('startup_timer'):
                 if self.local_only:
                     self.scheduled_start = self.startup_timer.dateTime().toPyDateTime()
                 else:
                     self.scheduled_start = self.startup_timer.dateTime().toPyDateTime().replace(second=0, microsecond=0)
+                # If the timer has actually passed already before the user hit Start, refuse to start the server.
+                if QtCore.QDateTime.currentDateTime().toPyDateTime() > self.scheduled_start:
+                    can_start = False
+                    Alert(self.common, strings._('gui_server_startup_timer_expired'), QtWidgets.QMessageBox.Warning)
             if self.common.settings.get('shutdown_timeout'):
                 if self.local_only:
                     self.timeout = self.shutdown_timeout.dateTime().toPyDateTime()
@@ -325,10 +330,9 @@ class ServerStatus(QtWidgets.QWidget):
                     self.timeout = self.shutdown_timeout.dateTime().toPyDateTime().replace(second=0, microsecond=0)
                 # If the timeout has actually passed already before the user hit Start, refuse to start the server.
                 if QtCore.QDateTime.currentDateTime().toPyDateTime() > self.timeout:
+                    can_start = False
                     Alert(self.common, strings._('gui_server_timeout_expired'), QtWidgets.QMessageBox.Warning)
-                else:
-                    self.start_server()
-            else:
+            if can_start:
                 self.start_server()
         elif self.status == self.STATUS_STARTED:
             self.stop_server()
diff --git a/share/locale/en.json b/share/locale/en.json
index d21052a5..a86341da 100644
--- a/share/locale/en.json
+++ b/share/locale/en.json
@@ -125,6 +125,7 @@
     "gui_tor_connection_lost": "Disconnected from Tor.",
     "gui_server_started_after_timeout": "The auto-stop timer ran out before the server started.\nPlease make a new share.",
     "gui_server_timeout_expired": "The auto-stop timer already ran out.\nPlease update it to start sharing.",
+    "gui_server_startup_timer_expired": "The scheduled time has already passed.\nPlease update it to start sharing.",
     "share_via_onionshare": "OnionShare it",
     "gui_connect_to_tor_for_onion_settings": "Connect to Tor to see onion service settings",
     "gui_use_legacy_v2_onions_checkbox": "Use legacy addresses",
diff --git a/tests/local_onionshare_share_mode_autostart_timer_too_short_test.py b/tests/local_onionshare_share_mode_autostart_timer_too_short_test.py
new file mode 100644
index 00000000..12343478
--- /dev/null
+++ b/tests/local_onionshare_share_mode_autostart_timer_too_short_test.py
@@ -0,0 +1,33 @@
+#!/usr/bin/env python3
+import pytest
+import unittest
+from PyQt5 import QtCore, QtTest
+
+from .GuiShareTest import GuiShareTest
+
+class LocalShareModeStartupTimerTooShortTest(unittest.TestCase, GuiShareTest):
+    @classmethod
+    def setUpClass(cls):
+        test_settings = {
+            "public_mode": False,
+            "startup_timer": True,
+        }
+        cls.gui = GuiShareTest.set_up(test_settings)
+
+    @classmethod
+    def tearDownClass(cls):
+        GuiShareTest.tear_down()
+
+    @pytest.mark.gui
+    def test_gui(self):
+        self.run_all_common_setup_tests()
+        self.run_all_share_mode_setup_tests()
+        # Set a low timeout
+        self.set_startup_timer(self.gui.share_mode, 2)
+        QtTest.QTest.qWait(3000)
+        QtCore.QTimer.singleShot(4000, self.accept_dialog)
+        QtTest.QTest.mouseClick(self.gui.share_mode.server_status.server_button, QtCore.Qt.LeftButton)
+        self.assertEqual(self.gui.share_mode.server_status.status, 0)
+
+if __name__ == "__main__":
+    unittest.main()