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Postbox sometimes cannot send messages with attachments

Sending messages via GMail sometimes results in a failure message. This invariably happens after the message has been delivered completely to the remote SMTP server, as the progress bar so nicely indicates. It is therefore not a connection or authentication issue, as the error message would lead you to believe ("there was a problem connecting to smtp.gmail.com, blah blah").

Given that Postbox is supposed to copy the message to the Sent folder after delivering it to the server, my guess is that it fails at this for some reason. Note that most messages are sent without problems; I suspect it only happens when the message has attachments of a certain size. The last message to fail had two 4MB PDF documents attached.

Retrying does not help. Either the message can be sent or not - retrying so far has never produced a different result. After a few tries I sent the message using GMail, which oddly enough shows all of my attempts at sending the message. In fact, it does show all of the attempts as actual sent messages, but only the one sent from the GMail interface actually reached the destination.

I can provide screenshots but am horribly busy so won't have time to do this or that to troubleshoot the problem, which is almost certainly a Postbox bug.
 
sad I’m frustrated
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