diff --git a/app/Entities/Tools/TrashCan.php b/app/Entities/Tools/TrashCan.php
index cc43b9096..c298169c3 100644
--- a/app/Entities/Tools/TrashCan.php
+++ b/app/Entities/Tools/TrashCan.php
@@ -15,6 +15,7 @@ use BookStack\Entities\Queries\EntityQueries;
 use BookStack\Exceptions\NotifyException;
 use BookStack\Facades\Activity;
 use BookStack\Uploads\AttachmentService;
+use BookStack\Uploads\Image;
 use BookStack\Uploads\ImageService;
 use BookStack\Util\DatabaseTransaction;
 use Exception;
@@ -217,14 +218,11 @@ class TrashCan
             ->where('default_template_id', '=', $page->id)
             ->update(['default_template_id' => null]);
 
-        // TODO - Handle related images (uploaded_to for gallery/drawings).
-        //   Should maybe reset to null
-        //   But does that present visibility/permission issues if they used to retain their old
-        //   unused ID?
-        //   If so, might be better to leave them as-is like before, but ensure the maintenance
-        //   cleanup command/action can find these "orphaned" images and delete them.
-        //   But that would leave potential attachment to new pages on increment reset scenarios.
-        //   Need to review permission scenarios for null field values relative to storage options.
+        // Nullify uploaded image relations
+        Image::query()
+            ->whereIn('type', ['gallery', 'drawio'])
+            ->where('uploaded_to', '=', $page->id)
+            ->update(['uploaded_to' => null]);
 
         $page->forceDelete();
 
@@ -275,8 +273,8 @@ class TrashCan
         // exists in the event it has already been destroyed during this request.
         $entity = $deletion->deletable()->first();
         $count = 0;
-        if ($entity) {
-            $count = $this->destroyEntity($deletion->deletable);
+        if ($entity instanceof Entity) {
+            $count = $this->destroyEntity($entity);
         }
         $deletion->delete();
 
diff --git a/database/migrations/2025_09_15_134751_update_entity_relation_columns.php b/database/migrations/2025_09_15_134751_update_entity_relation_columns.php
index 6fbeb1dd1..f8622d7c6 100644
--- a/database/migrations/2025_09_15_134751_update_entity_relation_columns.php
+++ b/database/migrations/2025_09_15_134751_update_entity_relation_columns.php
@@ -2,6 +2,7 @@
 
 use BookStack\Permissions\JointPermissionBuilder;
 use Illuminate\Database\Migrations\Migration;
+use Illuminate\Database\Query\Builder;
 use Illuminate\Database\Schema\Blueprint;
 use Illuminate\Support\Facades\Schema;
 
@@ -66,6 +67,15 @@ return new class extends Migration
         DB::table('images')->where('uploaded_to', '=', 0)->update(['uploaded_to' => null]);
         DB::table('activities')->where('loggable_id', '=', 0)->update(['loggable_id' => null]);
 
+        // Clean up any orphaned gallery/drawio images to nullify their page relation
+        DB::table('images')
+            ->whereIn('type', ['gallery', 'drawio'])
+            ->whereNotIn('uploaded_to', function (Builder $query) {
+                $query->select('id')
+                    ->from('entities')
+                    ->where('type', '=', 'page');
+            })->update(['uploaded_to' => null]);
+
         // Rebuild joint permissions if needed
         // This was moved here from 2023_01_24_104625_refactor_joint_permissions_storage since the changes
         // made for this release would mean our current logic would not be compatible with
diff --git a/tests/Entity/PageTest.php b/tests/Entity/PageTest.php
index 699414462..b9e1294e0 100644
--- a/tests/Entity/PageTest.php
+++ b/tests/Entity/PageTest.php
@@ -4,6 +4,7 @@ namespace Tests\Entity;
 
 use BookStack\Entities\Models\Book;
 use BookStack\Entities\Models\Page;
+use BookStack\Uploads\Image;
 use Carbon\Carbon;
 use Tests\TestCase;
 
@@ -158,6 +159,25 @@ class PageTest extends TestCase
         ]);
     }
 
+    public function test_page_full_delete_nulls_related_images()
+    {
+        $page = $this->entities->page();
+        $image = Image::factory()->create(['type' => 'gallery', 'uploaded_to' => $page->id]);
+
+        $this->asEditor()->delete($page->getUrl());
+        $this->asAdmin()->post('/settings/recycle-bin/empty');
+
+        $this->assertDatabaseMissing('images', [
+            'type' => 'gallery',
+            'uploaded_to' => $page->id,
+        ]);
+
+        $this->assertDatabaseHas('images', [
+            'id' => $image->id,
+            'uploaded_to' => null,
+        ]);
+    }
+
     public function test_page_copy()
     {
         $page = $this->entities->page();