Outlook authentication failed

Question

Hi, 

I recently bought a MacBook Pro. I installed 2016 Outlook (version 15.30) on my laptop. I have four accounts. 2 hotmail accounts (@hotmail.com), 1 university account (@uni.edu.au), and one iCloud account (******@icloud.com). On my previous Mac I was able to have all of my accounts on Outlook. This time, my iCloud would not link. I popup stating: 

'The server for account “iCloud” returned the error “[AUTHENTICATION FAILED] Authentication failed.” Your username/password or security settings may be incorrect. Would you like to try re-entering your password?'

appears when I try to link the account. After time, more of my emails weren't linking and popups would appear stating:

 'authentication failed, check your account information and try again'

I tried deleting one account and adding it back, but it will not add back with the same popup appearing. How do I get past this, it is really frustrating to log out and log back to different emails using Mozilla. I have tried deleting email passwords via keychain access, but that has not helped. any information would be greatly appreciated. I am not tech savvy, so please explain in layman's terms. thank you :)

Answer 1

Hi Bonnie,

For email accounts configured in Outlook for Mac, their passwords will be kept in the Keychain of Mac. According to the error message, it is more likely to be related to password (password stored in the Keychain or something like that). Since deleting the password entries in the Keychain doesn’t work, you may try the following methods to give it a shot:

1.   Reset default keychain.

Start the app Keychain Access

Open Preferences and select Reset My Default Keychain

2.    Reset your iCloud Keychain password.

Opening iCloud under the System Preferences pane

Click Options under Keychain

Click Change Security Code and follow the instructions

And, the current newest production version of Outlook 2016 for Mac is 15.31. You can try upgrading your client via clicking “Help”> “Check for updates” and see if the issue can be resolved.

By the way, I’d like to confirm whether you are configuring the 4 accounts under the same profile of Outlook 2016 for Mac. If so, please depart them into different profiles to check the result. You may refer toOutlook 2016 for Mac profile.

Regards,

Alan

Answer 2

Hi Bonnie,

Please feel free to let me know if you need any further help.

Regards,

Alan

Answer 3

Hi Alan,

I have the exact same problem with my Outlook 2016 for Mac v.15.33

I followed the instructions given by you above, but the problem persists. Extremely annoying that I can't use my Outlook for my iCloud mail accounts.

--

Brgds 

Lars, Norway

Answer 4

Hi all, 

I solved my authentication problem by enabling Two-factor Authentication. This may not be the core issue for folks who encountered this problem early on, but after June 15, 2017, Apple seemed to have turned up the enforcement of their two-factor authentication algorithm. Although I did't necessarily want to enable another form of authentication, I figured what the heck, if it works then great, and it did. Here's how...

Login into your iCloud account via your browser. Go to "Settings". Click on "Apple ID Manage", which will require you to login again, not sure why. Under "Security", turn on "Two-factor Authentication". My assumption is that you can always disable if needed. However, the process is rather involved, but the instructions are straightforward and provided. It involves adding a cell phone number to prompt for authentication when your iCloud account is used. After working through the enabling process, you'll see a link in this same SECURITY area of the page that reads "APP-SPECIFIC PASSWORDS". Here you can "Generate Password" to be used as your password in Outlook.

Good luck!

Alan N.