Mail never finishes sending?

>Yes, the limit is at the Mail Provider's end, disconnect from the Internet & wait for Mail to say it can't send, then choose edit & delete them.

Well, this didn't work. Dad had a Sending Message: 103.3MB at the bottom of Mail today, so I had him turn off his wifi, change his Energy Saver to keep awake for an hour (so Mail could continue trying to send), then checked back with him after 55 minutes, and mail was still trying to send. I'm assuming an hour would have been long enough for Mail to figure out there was no internet.

The curious thing is, if he quits mail, it doesn't try to send again when he starts it back up. Also, when this notification is present, there is no Outbox, so it's not possible for him to find whatever message is the culprit.

So I'm back hoping for new suggestions.

BDAqua wrote:

I've not seen a way to interrupt it other than force quitting Mail. it should time out & ask if you want to edit it or try later!???

You'd think so, wouldn't you? I mean, it should do that without taking any additional action, like disconnecting from the internet. But as noted above, we did disconnect from the internet, and an hour later it was still Sending Message: 103.3MB.

This wouldn't be so bad if quitting put the failed send back into the Outbox, where we could get at it. But it never does. Sometimes quitting means we never see that sending banner again (for that particular message), but sometimes it starts right back up again after re-launching Mail.

That makes total sense, BDAqua. We'll try that. Thanks!

Mail Drop is beyond him, and besides these are always FWD:FWD:FWDs from other 20th-century folks of some entire webpage someone though was funny and copy-pasted into an email because they didn't know how to just send a link. I've tried to get him to stop, but his way of "stopping" is to just not include me in the FWD so I don't know he's doing it. Grrr. (At least he knows better than to follow links from strangers or download anything without running it by me.)

Wifi only. We can try starting up in Safe Mode, but this happens randomly — it could be days, or even weeks before he sees this again. (Hence, why it was a month before I returned to this thread.) It will be hard to determine how long to run in Safe Mode before we think it's not happening because of Safe Mode vs. because it's just not happening.

Shouldn't there be a way to stop the send process? Or a way to find out what message is being sent? Anything we can do in Terminal to spy on the process, for example? Ages ago, Mail had the option of having a floating child window during the send process so you could see what was happening, but that appears to be gone.

I'm going to horse around with the Connection Doctor in the Window menu and see if I can gather more data.

Great idea. That may help us find the culprit and throw it away. As for preventing the problem from happening, I guess that's just going to be a bug report to Apple.

Will report back. Stay tuned.

/Love me some Find Any File — I use it more than Spotlight.

(For some reason, [Helpful] is grayed out for me or I'd have clicked it.

@BDAqua

I've got a Mail.app now, with data during one of these never-finishes-sending sessions. This one was only 1.3MB and still stuck.

I skimmed the log for PII and it doesn't seem like anything in there would be dangerous to share, but you'd know better than I would (I think). If I attached the log here, would that be helpful (and safe)?

EDIT: Forgot I had a screenie to attach.

Yeah, I'm a little concerned that it's working so hard on that. I mean, that's only 10 minutes of log, and it's 26000 lines. I can't imagine why it would need to do that. He's online every day, usually with Mail running, so it's not like it's catching up on anything he's done offline.

Thanks for asking! I'm still waiting for him to encounter the problem again. Trying to get him to notice when it's happening, I've had him launch the floating activity window. Will reply once we have something to go on.

Just dropping in to keep this thread from being archived. Problem hasn't resurfaced in a significant way as far as I know, but I don't consider the absence of recurrence to be a solution. Will be back to close this out one way or another.