Can't send mail with Apple Mail with Outlook.com due to SMTP

Question

To preface, I know for a fact that the password I am using is correct as per outlook.com's instructions and every tutorial I can get my hands on. It should be my password I use to enter the account, and IMAP is working beautifully. If it matters, I'm running Mavericks.

I get the following issue when I connect my outlook.com/live.com account with the Apple Mail app:

An error occurred while sending this message using the SMTP server “(null)”

It's the most vague error message I could get, next to:

"Trying to log in to this SMTP account failed. Verify that the username and password are correct."

The logs show this though:

WROTE Aug 30 14:45:10.421 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp-mail.outlook.com -- port:587 -- socket:0x6080008c9ca0 -- thread:0x608001467540
AUTH PLAIN  (*** 64 bytes hidden ***)

My theory was a TLS issue, but it seems that it is using it according to the logs despite my inability to select it in the app.

Answer 1

These are the settings I use to achieve the same thing...

smtp.outlook.com, with SSL
port: 587 authentication: Password
user name: full email address
TLS cert: None

If by any chance, that's on a BT-hosted office 365 account, the host names are changing soon, to outlook.office365.com for pop3 & smtp.office365.com for smtp; the other data remains the same. I've seen some outages over the past month on the old URLs. I switched mine to the new ones recently & have had no issues since, but officially, the change-over won't be until next year.
[All irrelevant, of course, if you're not on BT]

Setup pics included showing new office 365 settings, for the older outlook.com, just change that section, rest is the same.

Answer 2

It is a bug in Mail; go to Mail, then preferences, then select the account you are having problems with; highlight the outgoing server that does NOT say "offline" then save this setting and try again; worked for me.