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This is a multi-issue issue, which is better tracked as separate issues. (Something like this could be useful if describing work on a specific system to address the issues, but this one never functioned as that.)
The lack of a preview or other feedback is #2684. For the retry, I'm dubious that just always retrying is the right thing anyway. #3829 describes the foundational thing I think we want here, for messages in general; and we can file specific issues for further upload-specific wrinkles as we get into them.
Sending an image message takes two steps:
Two problems with that:
Ideally, we will track all image uploads and retry them if they fail.
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