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copied!<p>I was to solve this, although I'm still not sure if it's the most elegant solution.</p> <p>First off, I mentioned in my question that when I registered config_for_remote_upload with the before_validation callback, the file was not uploaded to S3, but the image_remote column was populated. Upon further inspection, the situation is even worse. When initializing the image_remote uploader within the before_validation callback, all files were deleted on the S3 storage bucket! I replicated this a couple times. I only tested when the store_dir was set to nil in the uploaded, thus putting the files at the root of the bucket.</p> <p>Initializing the image_remote column in during the before_save callback does not have this problem. In order force the record to save (it wouldn't save, because only a non db column attribute was being changed) I added a before_validation that changed the update_at field of the record.</p> <pre><code>before_validation: :change_record_updated_at ... def change_record_updated_at self.update_at=Time.current end </code></pre> <p>I also moved away from using dup, not because it didn't work, but rather because I didn't know why it worked. Instead I created a StringIO object for the file and assigned that to the image_remote column.</p> <pre><code> def config_for_remote_upload if self.remote.to_i==1 #self.image_remote = self.image.dup #this will open the file as binary img_binary = File.open(self.image.file.path){ |i| i.read } img_encoded = Base64.encode64(img_binary) io = FilelessIO.new(Base64.decode64(img_encoded)) io.original_filename = self.image.file.original_filename self.image_remote = io elsif self.remote.to_i==0 #delete remote image and clear field self.remove_image_remote = true end end </code></pre> <p>See <a href="https://stackoverflow.com/questions/6718841/restful-file-uploads-with-carrierwave">here</a> for further info on FilelessIO (StringIO with original_filename).</p> <p>With this configuration, the file can be uploaded to the second storage location (S3 in my case) after the initial upload.</p> <p>Hope this helps someone else out.</p>

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