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A fix for messages stuck in's Outbox Apps
Every few months for the last several years, this particular problem annoyed me enough that I searched this site and the web in general for a possible solution. The closest thing I'd ever found was the Workaround for a stuck outbound Mail message hint. But that doesn't describe the situation I've encountered. Maybe that's because the solution was obvious to everyone but myself. I find that hard to swallow.

I tend to use my PowerBook while disconnected. I also tend to send messages while disconnected, so they stay in my Outbox until I reconnect. Generally, it works. But every once in a while, a message gets stuck; flatly refuses to try to redeliver it. Synchronize Accounts does nothing (and never has). It used to be that sending another message via the same server would prod it into sending both messages, but somewhere along the way, Apple fixed that "feature." Usually quitting and restarting (a lame solution to my mind) would cause it to retry. Still, every once in a while, I'd still have messages that defy even that treatment.

Recently, I serendipitously stumbled upon the solution: Drag the offending messages to the Outbox folder in the folders pane (which you'll only have if you tried to send messages while offline). They'll be redelivered. Yes, I am aware of the Message » Send Again menu option. But there are times when I want/need to keep the Date header the same (yes, it can be forged) and the time stamp of the cryptographic signature the same as the original send date and time. Dragging the message to the Outbox accomplishes all of those things.
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A fix for messages stuck in's Outbox
Authored by: Fairly on Aug 21, '07 09:13:28AM

Wow. That's really cool.

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A fix for messages stuck in's Outbox
Authored by: erikogan on Aug 21, '07 10:10:55AM
Yeah, I'm really glad I stumbled upon it. I was also surprised that it wasn't documented anywhere.

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There are easier ways...
Authored by: ScienceMan on Aug 21, '07 08:30:01PM

Just click on the outbox, double-click on the unsent message to open it, and click on "Send" again. (This is different than using the "Message -> Send again" feature.)

It was never really broken -- you just didn't fully understand that unsent messages will stay there until an opportunity to retry sending them occurs. Mail is pretty good about detecting changes to network settings and trying again when this happens, but if you happen to know you are properly connected, the above procedure is a sure-fire way to try sending again.

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A fix for messages stuck in's Outbox
Authored by: Fairly on Aug 24, '07 11:09:34PM

Either that or move it out. And exit Mail, clean out your extraneous files in Mail's folder, and launch again. Works every time.

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