I have 11 messages stuck in Outbox that I tried to send from my MacBook Pro in the past 3 weeks. I recently upgraded to Maverick and prior to that I had NO problems sending emails. I AM able to send emails from my iPhone. I am a novice.

First thing I would do is run the Connection Doctor

Mail>Window>Connection Doctor

Try deleting your email passwords in Keychain.

Except in very rare circumstances it should not be necessary to pay anybody to help you with your Mac.

Here are instructions for my Leopard OS - I assume Mavericks is similar:

1. On Go menu (at top of screen) select Utilities
2. Double click Keychain Access
3. Select All items
4. Highlight an email related item
5. Hit delete key - or use Edit (at top of screen) > Delete
6. Repeat for other email related items

When you next use Mail your email provider will ask for your password. Normally once for outgoing email and once for incoming.

I'm not sure what you mean by 'stuck'. I've had a problems with Mavericks where it will send an email but leave a copy of it in the outbox (this is an issue with how mail saves intermediary drafts). These messages can just be deleted, because they've already been sent. I've seen problems where one email gets stuck (usually because of an oversized or corrupt attachment) and blocks other emails from being sent. deleting and (if necessary) resending that first stuck email will usually resolve that problem.

you can also try cleaning out and rebuilding the envelope index; can't hurt and often helps. Quit mail, open terminal.app, and run the following command:

sqlite3 ~/Library/Mail/V2/MailData/Envelope\ Index vacuum

1. Have you tried cleaning out the envelope index, as I suggested above?
2. Have you tried rebuilding the mailboxes? (Mailbox -> Rebuild)

Deleting items from the Keychain stops the Mac remembering your email password. Passwords sometimes get corrupted. Mail will ask you for your password when it next wants it.

This does not delete emails.

I assume you are using IMAP.

Try to use web access to your email provider. It may be easier to see what is happening on the web.

If you have not done this before Google something like: 'email web access for name-of-provider'.

Unless you have to use Outlook for a job, do not use Outlook. It's a mess & way too complicated.

I suggest switching to apple Mail or thunderbird. Since Outlook is busted, might as well switch now.l

You can get a gmail account and use it from a web browser.

Robert

This worked for me. I deleted the account from Keychain, quit Mail, then restarted it. It asked for my password (which I'd recently changed), I put it in, and voila, all my outbox mail went.

Here's my question: why does Mail go to Outlook at all? I don't have it on any of my other computers.

It would be better if you started your own thread.

I am not sure how Outlook came to be set up on your Mac.

You may find that the first item in Apple Mail preferences defines your default email client.

You may have to put your email account details into Apple Mail.

Also ensure that in future you open Apple Mail and not Outlook to send email.

I know I'm replying to an old thread, but I just found a fix on my end. Here's the strategy:

1. Open Mail
2. Click Mail>Preferences
3. Select the 'Accounts' Tab
4. Click the Drop-Down Menu Next to 'Outgoing Mail Server' and select 'Edit SMTP Server List'
5. A list of your accounts should appear. Click the advanced tab around the middle of the box. Then cycle through, clicking on your multiple accounts one at a time. If you find that one of your usernames and passwords is missing/incorrect, re-enter it, and click ok

I can't be 100% certain, but it appears the Outbox hangs up because in order to send messages from multiple addresses at once, it needs to authenticate all of them and then push them out from there. If even one of many is missing/incorrect, it will hold all messages until the issue is corrected. Hope this helps at least one other person!

"...try cleaning out and rebuilding the envelope index; can't hurt and often helps. Quit mail, open terminal.app, and run the following command:

sqlite3 ~/Library/Mail/V2/MailData/Envelope\ Index vacuum"

Bingo! Worked like a charm. Hoping it will hold, as other solutions (like restarting the Mac) just worked for a while before messages started hanging once again.