I can't send from my icloud email via Outlook 2011. Get Authentication error?

Same here... Just started in the last hour or so.

I'm having the same issue, and it, too, just started about an hour or an hour and half ago. I've double checked my settings, deleted, and re-added my iCloud account. I'm receiving email just fine. I can send from all my devices and from the iCloud website, but I can not, suddenly send from Outlook.

Any one else having same problem or have any suggestions?

Advice greatly appreciated!

Just a quick update. I deleted and re-entered iCloud again. Received the same error message. When Outlook brought up the dialogue box asking me if I wanted to try to re-enter my password, I said, "Yes." I then removed the @me.com from my USERNAME and merely used the first part of my email address. This, miraculously, solved the problem. How bizarre!

Excellent. This fixed the problem. Thanks for posting.

Brilliant, thanks. And as you say, bizarre. I've checked the set up pages on icloud support and they still say you have to enter your full email address as username. So how the **** does that happen?

Wow, it edited out the word for hades. Are we in church?

Thanks, very much!! it helped!! (Had Lost two full days, changing passwords, resetting SMTP, deleting & re-creating mail account, ... the works!!)

Holy cow.

This actually worked!

Great, thx a lot, well done 🙂

Thank you for the idea, worked for me to with an icloud address. Very grateful!

Thank you a thousand times over. I've spent hours trying to solve this issue and your solution worked!!!

I still have the same problem. I can receive, but not send mail. It has worked for years in my web based ERP system (Outlook settings), but suddenly not. I´ve tried everything and tend to get this error message:

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SMTP client failed to establish a secure connection to "smtp.mail.me.com" (17.172.34.225) on port 587
Would you like to disable SSL/TLS encryption?
The handshake failed due to an unexpected packet format.
00mm-asmtp004.mac.com -- Server ESMTP (Oracle Communications Messaging Server 7u4-27.08(7.0.4.27.7) 64bit (built Aug 22 2013))4.4.2 Timeout while waiting for command.

---

Have tried to disable SSL/TLS. Does it have to be port 587? Can i try another port? Any other suggestions?

I have the same problem...

I have Outlook 2011 for Mac - I have validated the settings and up until yesterday could send and receive emails using my .mac account.

I can send using icloud and mail (I use Outlook for work purposes) and can send in outlook using my work accounts.

My settings

Incoming server - imap.mail.me.com

Use SSL to connect checked.

Outgoing server - smtp.mail.me.com - I also changed it to p06-smtp.mail.me.com

override default port checked (port 587)

use SSL to connect checked

authentication - Username and password.

I have rebuilt the database - no effect.

I have deleted the @me.com from the username.

I continue to get the error

"Mail could not be sent

The server for account "mac" returned the error. 5.7.8. Bad Username or password (Authentication failed..)" Your username/password or security settings may be incorrect. Would you like to try rentering your password"

I have validated my username and password and rentered them both.

I have emptied the outbox and retried but nothing works.

Thanks for the help.

You are a legend, You should get a Job with Apple and teach them how to fix issues, I have been trying for weeks to get this issue fixed and when you call the support centre they tell me it's a Microsoft issue, and when I call Microsoft they tell me it's an ICloud issue which has to do with Apple. Mate If I could shout you a beer right now i would do it with all my heart. Thanks again champ, you put a big smile to my face.

Cheers