diff --git a/app/jobs/scheduled/clean_up_uploads.rb b/app/jobs/scheduled/clean_up_uploads.rb
index ef05762bd..523a017c4 100644
--- a/app/jobs/scheduled/clean_up_uploads.rb
+++ b/app/jobs/scheduled/clean_up_uploads.rb
@@ -10,13 +10,13 @@ module Jobs
 
       Upload.where("created_at < ?", grace_period.hour.ago)
             .where("retain_hours IS NULL OR created_at < current_timestamp - interval '1 hour' * retain_hours")
-            .where("id NOT IN (SELECT upload_id FROM post_uploads)")
-            .where("id NOT IN (SELECT uploaded_avatar_id FROM users)")
-            .where("id NOT IN (SELECT gravatar_upload_id FROM user_avatars)")
-            .where("url NOT IN (SELECT profile_background FROM user_profiles)")
-            .where("url NOT IN (SELECT card_background FROM user_profiles)")
-            .where("url NOT IN (SELECT logo_url FROM categories)")
-            .where("url NOT IN (SELECT background_url FROM categories)")
+            .where("id NOT IN (SELECT upload_id FROM post_uploads WHERE upload_id IS NOT NULL)")
+            .where("id NOT IN (SELECT uploaded_avatar_id FROM users WHERE uploaded_avatar_id IS NOT NULL)")
+            .where("id NOT IN (SELECT gravatar_upload_id FROM user_avatars WHERE gravatar_upload_id IS NOT NULL)")
+            .where("url NOT IN (SELECT profile_background FROM user_profiles WHERE LENGTH(COALESCE(profile_background, '')) > 0)")
+            .where("url NOT IN (SELECT card_background FROM user_profiles WHERE LENGTH(COALESCE(card_background, '')) > 0)")
+            .where("url NOT IN (SELECT logo_url FROM categories WHERE LENGTH(COALESCE(logo_url, '')) > 0)")
+            .where("url NOT IN (SELECT background_url FROM categories WHERE LENGTH(COALESCE(background_url, '')) > 0)")
             .destroy_all
     end
 
diff --git a/spec/jobs/clean_up_uploads_spec.rb b/spec/jobs/clean_up_uploads_spec.rb
index 9c307b7fc..6035f17fc 100644
--- a/spec/jobs/clean_up_uploads_spec.rb
+++ b/spec/jobs/clean_up_uploads_spec.rb
@@ -3,8 +3,21 @@ require 'rails_helper'
 require_dependency 'jobs/scheduled/clean_up_uploads'
 
 describe Jobs::CleanUpUploads do
-  it "runs correctly without crashing" do
+
+  before do
+    Upload.destroy_all
     SiteSetting.clean_up_uploads = true
-    Jobs::CleanUpUploads.new.execute(nil)
+    SiteSetting.clean_orphan_uploads_grace_period_hours = 1
   end
+
+  it "deletes orphan uploads" do
+    Fabricate(:upload, created_at: 2.hours.ago)
+
+    expect(Upload.count).to be(1)
+
+    Jobs::CleanUpUploads.new.execute(nil)
+
+    expect(Upload.count).to be(0)
+  end
+
 end