diff --git a/qt/aqt/addons.py b/qt/aqt/addons.py
index 6d692626d..472419556 100644
--- a/qt/aqt/addons.py
+++ b/qt/aqt/addons.py
@@ -726,6 +726,7 @@ class AddonsDialog(QDialog):
     def __init__(self, addonsManager: AddonManager) -> None:
         self.mgr = addonsManager
         self.mw = addonsManager.mw
+        self._require_restart = False
 
         super().__init__(self.mw)
 
@@ -768,6 +769,8 @@ class AddonsDialog(QDialog):
         self.onInstallFiles(paths)
 
     def reject(self) -> None:
+        if self._require_restart:
+            tooltip(tr.addons_changes_will_take_effect_when_anki(), parent=self.mw)
         saveGeom(self, "addons")
         aqt.dialogs.markClosed("AddonsDialog")
 
@@ -854,6 +857,7 @@ class AddonsDialog(QDialog):
     def onToggleEnabled(self) -> None:
         for module in self.selectedAddons():
             self.mgr.toggleEnabled(module)
+        self._require_restart = True
         self.redrawAddons()
 
     def onViewPage(self) -> None:
@@ -885,6 +889,9 @@ class AddonsDialog(QDialog):
             return
         gui_hooks.addons_dialog_will_delete_addons(self, selected)
         for module in selected:
+            # doing this before deleting, as `enabled` is always True afterwards
+            if self.mgr.addon_meta(module).enabled:
+                self._require_restart = True
             if not self.mgr.deleteAddon(module):
                 break
         self.form.addonList.clearSelection()
diff --git a/qt/aqt/main.py b/qt/aqt/main.py
index 184e028cd..32004b81c 100644
--- a/qt/aqt/main.py
+++ b/qt/aqt/main.py
@@ -31,7 +31,16 @@ from anki.decks import DeckDict, DeckId
 from anki.hooks import runHook
 from anki.notes import NoteId
 from anki.sound import AVTag, SoundOrVideoTag
-from anki.utils import dev_mode, ids2str, int_time, is_lin, is_mac, is_win, split_fields
+from anki.utils import (
+    dev_mode,
+    ids2str,
+    int_time,
+    is_lin,
+    is_mac,
+    is_win,
+    point_version,
+    split_fields,
+)
 from aqt import gui_hooks
 from aqt.addons import DownloadLogEntry, check_and_prompt_for_updates, show_log_to_user
 from aqt.dbcheck import check_db
@@ -713,7 +722,6 @@ class AnkiQt(QMainWindow):
         gui_hooks.state_did_change(state, oldState)
 
     def _deckBrowserState(self, oldState: str) -> None:
-        self.maybe_check_for_addon_updates()
         self.deckBrowser.show()
 
     def _selectedDeck(self) -> DeckDict | None:
@@ -933,7 +941,7 @@ title="{}" {}>{}</button>""".format(
         last_check = self.pm.last_addon_update_check()
         elap = int_time() - last_check
 
-        if elap > 86_400:
+        if elap > 86_400 or self.pm.last_run_version() != point_version():
             check_and_prompt_for_updates(
                 self,
                 self.addonManager,
@@ -1112,6 +1120,7 @@ title="{}" {}>{}</button>""".format(
     ##########################################################################
 
     def closeEvent(self, event: QCloseEvent) -> None:
+        self.pm.set_last_run_version()
         if self.state == "profileManager":
             # if profile manager active, this event may fire via OS X menu bar's
             # quit option
diff --git a/qt/aqt/profiles.py b/qt/aqt/profiles.py
index 07c86ec6e..e4756c231 100644
--- a/qt/aqt/profiles.py
+++ b/qt/aqt/profiles.py
@@ -20,7 +20,7 @@ from anki.collection import Collection
 from anki.db import DB
 from anki.lang import without_unicode_isolation
 from anki.sync import SyncAuth
-from anki.utils import int_time, is_mac, is_win
+from anki.utils import int_time, is_mac, is_win, point_version
 from aqt import appHelpSite
 from aqt.qt import *
 from aqt.theme import Theme
@@ -499,6 +499,12 @@ create table if not exists profiles
     # Shared options
     ######################################################################
 
+    def last_run_version(self) -> int:
+        return self.meta.get("last_run_version", 0)
+
+    def set_last_run_version(self) -> None:
+        self.meta["last_run_version"] = point_version()
+
     def uiScale(self) -> float:
         scale = self.meta.get("uiScale", 1.0)
         return max(scale, 1)