After it accepts your password, the password area for your iCloud account will be empty. Then on your Mac, when Outlook prompts for a password, this password does not go in the password area of the account, but the Mac password prompt that goes in the keychain.
Directions below on how to get it connected again. | 3 Comments iCloud password not working Outlook 2016 Mac If you’re getting the error on the right side or having issues connecting your iCloud account with Outlook 2016 on your Mac, then you have an app password issue.