Cannot send emails with my iCloud email address in Outlook for Mac 2011 and get error message 5.7.8

Just keep trying various combinations, or set it up in Mac mail and copy the settings (more sensibly just stop with the Outlook thing altogether)

Try with your full email address and wiith just the username part of it. Ensure that ports (smtp 587, imap 993) are correct

But my experience is that Outlook is a mediocre Imap client, and iCloud is an Imap system.

I have used Outlook for 2 years and entourage for a while and now it suddenly stops, which seems odd.

It is odd, but predictably so (everything works before it breaks).

However, the fact that other clients work does limit the damage and narrow the focus to Outlook, you may just need to wait until whatever quirk is causing this goes away. You can retrace some of the obvious routes (reboot, remove the account and then remake it)

All of which really means I have no new ideas, sorry.

I'm in the exact same boat. Happened around the same time. I've removed and re-installed the email address as well as Outlook. I can receive emails but can't send - same error code 5.7.8

Apple support acts like they've never used Outlook and also said that the smtp address and port could be the problem - smtp.mail.me.com and port is 587. But according to them, it's assigned by outlook so this is an outlook problem and they won't help. Not sure what to do. I can use it fine from web and from iMail. Please update if you find a solution. Going bananas over here!

I have the same problem too over the last week. Initially I thought it was a password problem and reset my Apple ID password - that fixed it for a week. I couldn't reuse the same password and have had to reset all of my devices and email clients. Now the same thing has happened again with Outlook 2011 reporting error 5.7.8 "Bad username or password (Authentication Error) again. I can recieve @me.com email but not send in Outlook 2011. Apple's Mail app works fine. Beginning to tear my hair out now. This is a recurring problem.

SMTP.mail.me.com is the recommended (by Apple) server, SSL on, the port is 587.

The username should be the full iCloud address but many report that just using the part before the @ sign works sometimes.

The password must meet iCloud minima (8 characters, at least 1 uppercase, 1 lowercase and one number, no special characters)

Make sure you meet those requirements.

That's exactly what I'm using. It returns an error code 5.7.8 - bad username/password

I know that I'm using the correct username and password - i can log in through the web and can receive emails through outlook. Just can't send them. Any other ideas? I also tried port 25 &465. No luck.

Change your password, make sure to meet the minimum requirements

Already did that too. Since I can send/receive through my phone, web, and iMail - I can't help but think that this IS an outlook thing and that it's related to the port. I don't know anything else to try.

Does it work in Mail (on your Mac)?

Yes... Works everywhere except in outlook.

If everything except Outlook works it is time to seek help from Microsoft, 😟

Yeah.. Well, Microsoft "can't help me" because I'm on a Mac using mobileme for mail. They say that it's apple's problem and apple says that it's microsoft's problem. Nobody will help. It's enfuriating. Thanks for the suggestions anyway!

Which do you think is not working, Apple's mail system (the one that works everywhere except Outlook) or Outlook?

When did you last update Outlook?

Hi All,

I had this issue with Outlook & Win7 and I figured out a solution. The problem seems to be with Apple and affects some using Outlook. The issue seems to stems from the PW problem that happened a few weeks ago with iCloud. This solution is for Outlook & Win7. But you can try it using the same for Outlook & Mac.

First the servers, port and encryption you should be using are as follows;

Incoming Mail Server: imap.mail.me.com

Port: 993

Encryption Connection: SSL

Outgoing Mail Server: smtp.mail.me.com

Port: 587

Encryption Connection: Auto

What I did to correct the issue.

1 - I went in to Outlook and then into the Account Setting for iCloud.

2 - Selected "More Settings"

3 - Selected the "Outgoing Server" tab

4 - Make sure you check the box next to "My outgoing server (SMTP) requires authentication"

5 - Click on the Radio button that says "LOG ON USING"

6 - For "User Name" enter your FULL email address.

7 - Password, Now here is where the issue is use your OLD password. The password that you used BEORE you changed it when Apple had the issue. For some reason Apples smtp servers are retaining your OLD SMTP password. When you changed your password it did nto change for SMTP.

8 - Now you have to make one more change. On the "Advanced" tab under "Outgoing Server" make sure port number is set to "587" AND "encryption connection" is set to "Auto"

When I manually enter my OLD password using the information I provided above I can send email from my iCloud account through Outlook.