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I do not understand why it currently works the way it does. The attachment table carries the content type, so there is no reason one could not have a media gallery reference in the attachment table that referenced an attachment_data entry that was originally loaded in a post. The developers are reluctant to move the attachment details regarding thumbnail, etc. to the attachment table from the attachment_data table. When that was brought up in another improvement thread it was rejected. If the thumbs were the same size in media, posts and conversations, it would not be a problem.

If someone wanted to create an addon that worked "correctly" they would need to add another attachment_resolve table to handle the conflict.