Mail stuck in OUTBOX

Having the same issue here. Only thing that's changed recently is upgrade to 10.5.2

Emails act like they're being sent, but then just stay in outbox and never get picked up.

Connection doctor shows all connections are fine. Have tried restarting mail and even the computer, with no success.

Exact same issue here...using AT&T uverse as my ISP. The other odd behavior I'm noticing is that my emails are unable to be deleted...I highlight one, hit delete (or right click delete) and it looks gone, but never shows up in the trash. I can click off the mailbox, then click on to it again and yep, email is STILL there.

I've tried a number of things...

1. I rolled back to a month ago's version of Mail.app and the entire /Library/Mail folder using Time Machine and reloaded all my accounts. Didn't work, same result.

2. I totally re-installed Mail.app from Leopard install disc. Didn't work.

The weird thing is that I can still work everything fine on my wireless Macbook 10.5.2 account. Everything works flawlessly as before. I'm guess it's something about the wired network going through the AT&T router? I'm going to do some more tests and post...

I think i'm back up and running.

The steps I took...downloaded and reinstalled 10.5.2 from Apple's website...restarted...didn't fix it.

Removed and re-setup my two IMAP accounts from the preferences pane...restarted and presto. It works. Everything is back to normal.

Having the same problem. AT&T is my ISP. I have POP and IMAP accounts. All attempts just sit in the outbox. I've tried deleting and re-adding the accounts. I've restarted the computer. Connection doctor shows good connections. Mail just will not send. I've been at it for hours to no avail.

I removed Mail 3.2 and installed 3.0 from the Leopard disc. It's working fine so far with the exception of a few IMAP hiccups. I can send mail though. I think I'll just refrain from upgrading that app for the time being.

I too can confirm having this problems since the last Apple security update. Currently, having to quit mail, relaunch, open email in outbox and hit send again to get it to deliver. Will post back when I find a solution.

Mail seems to be working again.

Did a Safe Boot. While in Safe Mode launched Mail and sent a test email which did not hang in the Outbox. Restarted again and all seems to be working.

Tech support once told me a safe boot can sometimes clear things up. I'm not a systems engineer so I don't fully get it. Nonetheless, it seems to have fixed my issue with outgoing mail getting hung up in the outbox.

See: http://docs.info.apple.com/article.html?artnum=107392

The same problem happened to me when I switched over to AT&T.
I solved this problem by using Time Machine to restore my Mail preferences file:
~/Library/Preferences/com.apple.mail.plist

to a time previous to when the ATT mail setup program was run.

I ran the ATT installation disk when my DSL service was installed and while Mac Mail worked fine with my existing .Mac and POP3 accounts, it wouldn't connect to the newly created ATT.net account. ATT support provided a special Mail setup executable. After running that, the new ATT.net account worked but all outbound mail, regardless of the originating account, would be stuck in the Outbox. Inbound mail continued to come in just fine.

After restoring the preferences file, everything worked fine and I manually re-added my new ATT POP3 account.

The problem is a corrupt Outbox. I read about this on
the ATT trouble shooting site. Delete the Outbox and
mail will create a new one. This solved my problem with
email sitting the Outbox forever and never being sent.
To be safe, I dragged my Outbox to a different location,
then started mail. Problem solved!

The Outbox is found: Users/YourName/Library/Mail/Mailboxes/Outbox.mbox

Delete the Outbox.mbox folder and start mail.

I am having the same problem as described above, and was hopeful when I read the two solutions - safe mode reboot and deleting outbox.mbox. Unfortunately neither solution worked for me. Any other ideas? I have a few email accounts set up and it won't send mail from any of them - just goes to the Outbox. The same exact settings on my MacBook work perfectly fine.

I am suddenly having this problem as well. Tried the solutions to no avail. Also my Macbook email works perfectly fine. Go figure. This is a really annoying issue.

Same problem. Follows adding ATT/Yahoo account, to two others.
Delete outbox mbox not help.

Same issue - this happened when I got my first ATT uverse account a few months ago, but I don't remember how it was resolved (although my mail did not send at all and had to use Thunderbird). Just moved and had to get a new account through ATT and now it is happening again. I am not technically inclined at all, so I don't know what half this stuff means and am afraid if I delete my outbox something horrible will happen. I think I have Time Machine with Leopard, but I don't think it works because I haven't set it up. I sound like a complete idiot right now, but any other further clarifications to this would be greatly appreciated. I don't want to have to switch back to Thunderbird.

I also have ATT DSL. Removing the outbox solved the issue for me

Nice work all!

Same problem, switched from A&T DSL to AT&T U-verse almost 2 months ago and ever since mail hangs in outbox. I can close mail and then open message in outbox and send successfully but must do this each time I want to send email.