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Here's a proposed overhaul of the Add/Replace File + Reply/Attach buttons at the bottom of each message:
Reply/Attach menu as is, and it becomes the only button in those locations.
File menu for managing the one file associated with a message.
When there isn't already a file: File menu appears only when editing message.
Add File can go here, perhaps renamed to something like "Embed Single File"
This reduces the prominence of "Add File" by two levels: you have to be editing, then you have to click File / Add File
When there is already a file: File menu is always next to the attachment top (where it says size and file type)
Replace File can go here
(Do we still want it next to Reply/Attach too, for easier discoverability? I think less necessary now that File will always be visible in a message with a file.)
Extract File into Reply: make new reply and move the message there
Move File: select another message to move the file to (target message must have no file currently)
Copy File: select another message to embed the same file in (via a pointer to the same file object); this is useful when you want the same image in two different threads, for example.
Perhaps only for Superusers? Rare that users need this level of control... But also not a dangerous operation, so maybe fine.
Remove File, in red, but this still needs a confirmation dialog
When viewing history, and there is a file:
Restore File: re-use this old version in current version of message (if they're not the same)
Extract File: like above, but without changing message
Here's a proposed overhaul of the Add/Replace File + Reply/Attach buttons at the bottom of each message:
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