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What problem I am trying to solve? When an encrypted message is crafted and the image is added - discourse needs a hard refresh to display that image. What is happening? Everything starts here - when the upload is finished we add serialized object to the cache https://github.com/discourse/discourse/blob/master/app/assets/javascripts/discourse/components/composer-editor.js#L748:L757 Then, `discourse-encrypt` is trying to get an image from the cache and use `short_path` property https://github.com/discourse/discourse-encrypt/blob/master/assets/javascripts/discourse/initializers/hook-decrypt-post.js.es6#L142:L143 Why is it working after a hard refresh? After refresh, we populate cache once again using that function: https://github.com/discourse/discourse/blob/master/app/assets/javascripts/pretty-text/upload-short-url.js#L11:L17 And lookup_urls method from backend is returning `short_path` https://github.com/discourse/discourse/blob/master/app/controllers/uploads_controller.rb#L55:L64 TL;DR We should expose short path in upload serializer. I ensured that this serializer is used only when attachments are uploaded so it should not affect performance.