But something changed very recently and very badly.The Mail and Calendar apps for Windows 10 don't support two-factor authentication. These are accounts and settings that haven't moved for years and have worked throughout mac upgrades/migrations etc etc. For one reason or another on ONE of my Macs all the gmail accounts (5 of them - which all have 2fa) stopped working (server offline problem reported and the little broken connection icon appearing in Apple Mail). If you still get a username or password error, contact the email provider or system administrator.I have a couple of macs (sharing keychains via iCloud) and a few iOS devices (also sharing keychains via iCloud).
Mail App Not Accepting Code ResponseTo ForceA Microsoft 365 subscription offers an ad-free interface, custom domains, enhanced security options, the full desktop version of Office, and 1 TB of cloud storage.Running connection doctor (and doing some tcpdump'ing to make sure that was all ok), looking at the SMTP messages between the broken mac and gmail servers the problem was being flagged on a 501 error line: 5.5.2 Cannot Decode responseTo force Mac mail to accept your email password again and remove the repeated prompt, follow the steps to manually update your email account password below. Weve developed a suite of premium Outlook features for people with advanced email and calendar needs. An app password is used instead of your normal account password for apps that don't support two-factor authentication.Expand your Outlook.Try as I might I could not get a password to 'stick' in that box and remain there.Office 365 user name and password required: None: One or more static IP. In particular one odd thing was going on, re-entering the app specific password in the SMTP connections, and setting the account name to be looked fine to start with, then a few seconds later the SMTP server connection would go offline, and re-opening the SMTP settings panel showed a blank password again. Enter your password in the required fields where it is blank.I re-checked all of the smtp settings (username trying the different ports, and playing around using different authentication schemes), dug into keychain to see if there was anything odd going on there, and differences between the keychains on the two macs. Select your mail account and choose server settings. Android emulator home shortcut macBut before reinstalling them I removed all of the gmail keychain entries using keychain access (in your utilities folder if you are following along at home) - note that removing the gmail accounts from the internet accounts panel does not clear out the keychain entries (which appears to be one of the confusing things here - you have to go and do that yourself). The password in the SMTP connection settings was simply not being recorded correctly, or there was some odd clash going on between keychain and apple mail.So again, I removed all the accounts using the system preferences internet accounts panel. Same problem, they worked on one mac, but still not on the broken mac.
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