diff --git a/db/migrate/20251002140103_migrate_timeline_preview_setting.rb b/db/migrate/20251002140103_migrate_timeline_preview_setting.rb
index 4d180bd8f3..9a18a6451c 100644
--- a/db/migrate/20251002140103_migrate_timeline_preview_setting.rb
+++ b/db/migrate/20251002140103_migrate_timeline_preview_setting.rb
@@ -12,8 +12,7 @@ class MigrateTimelinePreviewSetting < ActiveRecord::Migration[8.0]
     Setting.upsert_all(
       %w(local_live_feed_access remote_live_feed_access local_topic_feed_access remote_topic_feed_access).map do |var|
         { var: var, value: value ? "--- public\n" : "--- authenticated\n" }
-      end,
-      unique_by: :var
+      end
     )
   end
 
diff --git a/db/migrate/20251023210145_migrate_landing_page_setting.rb b/db/migrate/20251023210145_migrate_landing_page_setting.rb
index 0067e17185..e8448bc75e 100644
--- a/db/migrate/20251023210145_migrate_landing_page_setting.rb
+++ b/db/migrate/20251023210145_migrate_landing_page_setting.rb
@@ -9,10 +9,10 @@ class MigrateLandingPageSetting < ActiveRecord::Migration[8.0]
 
     value = YAML.safe_load(setting.attributes['value'], permitted_classes: [ActiveSupport::HashWithIndifferentAccess, Symbol])
 
-    Setting.upsert(
+    Setting.upsert({
       var: 'landing_page',
-      value: value ? "--- trends\n" : "--- about\n"
-    )
+      value: value ? "--- trends\n" : "--- about\n",
+    })
   end
 
   def down; end
diff --git a/lib/tasks/tests.rake b/lib/tasks/tests.rake
index 9385e390de..0c5c6a09ca 100644
--- a/lib/tasks/tests.rake
+++ b/lib/tasks/tests.rake
@@ -144,6 +144,16 @@ namespace :tests do
         exit(1)
       end
 
+      unless Setting.landing_page == 'about'
+        puts 'Landing page settings not migrated as expected'
+        exit(1)
+      end
+
+      unless Setting.local_live_feed_access == 'authenticated'
+        puts 'Local live feed access not migrated as expected'
+        exit(1)
+      end
+
       puts 'No errors found. Database state is consistent with a successful migration process.'
     end
 
@@ -162,6 +172,13 @@ namespace :tests do
           (1, 'https://example.com/users/foobar', 'foobar@example.com', now(), now()),
           (1, 'https://example.com/users/foobar', 'foobar@example.com', now(), now());
 
+        /* trends_as_landing_page is technically not a 3.3.0 setting, but it's easier to just add it here */
+        INSERT INTO "settings"
+          (id, thing_type, thing_id, var, value, created_at, updated_at)
+        VALUES
+          (7, NULL, NULL, 'timeline_preview', E'--- false\n', now(), now()),
+          (8, NULL, NULL, 'trends_as_landing_page', E'--- false\n', now(), now());
+
         /* Doorkeeper records
            While the `read:me` scope was technically not valid in 3.3.0,
            it is still useful for the purposes of testing the `ChangeReadMeScopeToProfile`