diff --git a/src/Http/Controllers/Configuration/ScheduleController.php b/src/Http/Controllers/Configuration/ScheduleController.php
index 64a9eb6b1..6aef76ebe 100644
--- a/src/Http/Controllers/Configuration/ScheduleController.php
+++ b/src/Http/Controllers/Configuration/ScheduleController.php
@@ -118,8 +118,11 @@ public function createSchedulingRule(Request $request)
         $rule->filter = $request->filters;
         $rule->save();
 
-        RefreshToken::all()->each(function ($token) {
-            CharacterSchedulingRule::updateRefreshTokenSchedule($token);
+        // chunk this to avoid out-of-memory issues on large installs
+        RefreshToken::chunk(200, function ($tokens) {
+            foreach ($tokens as $token) {
+                CharacterSchedulingRule::updateRefreshTokenSchedule($token);
+            }
         });
 
         return redirect()->back()
@@ -134,8 +137,11 @@ public function deleteSchedulingRule(Request $request)
 
         CharacterSchedulingRule::destroy($request->rule_id);
 
-        RefreshToken::all()->each(function ($token) {
-           CharacterSchedulingRule::updateRefreshTokenSchedule($token);
+        // chunk this to avoid out-of-memory issues on large installs
+        RefreshToken::chunk(200, function ($tokens) {
+            foreach ($tokens as $token) {
+                CharacterSchedulingRule::updateRefreshTokenSchedule($token);
+            }
         });
 
         return redirect()->back()->with('success', 'Successfully removed character scheduling rule!');
diff --git a/src/Models/CharacterSchedulingRule.php b/src/Models/CharacterSchedulingRule.php
index 471a5f6f7..e903f5bd4 100644
--- a/src/Models/CharacterSchedulingRule.php
+++ b/src/Models/CharacterSchedulingRule.php
@@ -66,6 +66,7 @@ public static function updateRefreshTokenSchedule(RefreshToken $token): void
         if($schedule === null) {
             $schedule = new RefreshTokenSchedule();
             $schedule->character_id = $token->character_id;
+            $schedule->last_update = now()->subYears(10); // Hopefully this is far enough in the past to mean never?
         }
 
         $schedule->update_interval = self::getCharacterSchedulingInterval($token->character);