diff --git a/app/models/upload.rb b/app/models/upload.rb
index 559ad0cb685..458fb358455 100644
--- a/app/models/upload.rb
+++ b/app/models/upload.rb
@@ -39,6 +39,11 @@ class Upload < ActiveRecord::Base
 
   validates_with UploadValidator
 
+  before_destroy do
+    UserProfile.where(card_background_upload_id: self.id).update_all(card_background_upload_id: nil)
+    UserProfile.where(profile_background_upload_id: self.id).update_all(profile_background_upload_id: nil)
+  end
+
   after_destroy do
     User.where(uploaded_avatar_id: self.id).update_all(uploaded_avatar_id: nil)
     UserAvatar.where(gravatar_upload_id: self.id).update_all(gravatar_upload_id: nil)
diff --git a/spec/models/upload_spec.rb b/spec/models/upload_spec.rb
index e95aa43d18e..9049a6d1f1e 100644
--- a/spec/models/upload_spec.rb
+++ b/spec/models/upload_spec.rb
@@ -413,4 +413,25 @@ describe Upload do
       "https://#{SiteSetting.s3_upload_bucket}.s3.amazonaws.com/original/1X/#{upload.sha1}.#{upload.extension}?acl"
     )
   end
+
+  context '.destroy' do
+
+    it "can correctly clear information when destroying an upload" do
+      upload = Fabricate(:upload)
+      user = Fabricate(:user)
+
+      user.user_profile.update!(
+        card_background_upload_id: upload.id,
+        profile_background_upload_id: upload.id
+      )
+
+      upload.destroy
+
+      user.user_profile.reload
+
+      expect(user.user_profile.card_background_upload_id).to eq(nil)
+      expect(user.user_profile.profile_background_upload_id).to eq(nil)
+    end
+
+  end
 end