I have tested this, and it is true that you cannot insert pictures (or
other files) over certain protocols, such as Jabber or MSN. However, you
can insert pictures (and only pictures) directly into the conversation
in other protocols such as AIM. I think that for protocols that support
inserting, it should insert the file. If they only support sending, it
should start sending the file. Otherwise, this feature should be
disabled.

** Bug 64868 has been marked a duplicate of this bug

** Changed in: gaim (Ubuntu)
       Status: Unconfirmed => Confirmed

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[2.0beta3] Cannot send a picture by drag-n-dropping
https://launchpad.net/bugs/38235

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