iCloud mail with two-factor authentication

Commodore

Senior Member
Outlook version
Outlook 2013 32 bit
Email Account
IMAP
Today my Outlook 2013 stopped working with iCloud email account. At first I thought it was one of the semi-regular issues when Outlook starts asking for password for no reason (and restart usually helps), but turned out this wasn't the case. The issue remained even after a reboot, so I removed the iCloud IMAP account from Outlook, and tried to add it from scratch. However, I wasn't able to do it as it failed at "Test Account Settings" already.

So I turned the two-factor authentication on via my iCloud website (Apple did send an email a few days ago in this regard). I added an "app-specific password" there (that was pretty much it - it saved the generated password, nothing else). I tried adding the iCloud/me.com account again, but still stuck at Test Account Settings (I tried either the usual account password or the "app-specific" one, nothing worked).

Any idea how this should work now? I don't remember any secondary password prompts with Outlook ever. Will we need to install some addons?
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
it should work with the app password. i'll test it here...

You'll need to use the app password in outlook - at this time (and probably for some time to come), you'll need to use the app password as outlook doesn't support the second screen except for business office 365 accounts.
 

Commodore

Senior Member
Outlook version
Outlook 2013 32 bit
Email Account
IMAP
So if I get this right - the username is "[username]@me.com", and the password is now the app-specific one instead of the Apple account one?
How about SMTP tab, should the "use same settings as my incoming server" still be checked?


EDIT: I somehow managed to make it work. The SMTP check was OK, as for the outgoing encryption, I used TLS at 587 port (I'm pretty sure it was SSL before). Maybe their servers were just "overwhelmed" yesterday.
 
Last edited:

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
correct - use your apple id address and the app password, smtp should use the same as the incoming server.

On TLS: this is the new and improved ssl - most, if not all, of the major mail servers should be using this now - smaller ones may still use ssl for now but eventually all will use tls.
 

Commodore

Senior Member
Outlook version
Outlook 2013 32 bit
Email Account
IMAP
Outlook now often (if not with every automatic send/receive or IMAP sync) opens the dialog box "Enter your user name and password for the following server ... imap.mail.me.com" (even though the credentials have been saved). Any idea what could be the problem? If I click OK, it continues the "sync", otherwise it gives an error.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
this is with the app password in it? No other error messages?
 

Commodore

Senior Member
Outlook version
Outlook 2013 32 bit
Email Account
IMAP
Yes, the app-specific password. Nope, no errors. The credentials are saved, as before. I get the dialog box - I click OK, it goes through, I click Cancel, it gives an error. This is with the scheduled send/receive. If I click the me.com's Inbox (or any other folder), everything's ok.
 

Commodore

Senior Member
Outlook version
Outlook 2013 32 bit
Email Account
IMAP
Seems this issue comes and goes, so I suppose it's on Apple's side (maybe not all accounts).
 
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