Gmail and Apple Mail App: Cannot send message using the server SMTP

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Jack

I have the same problem with a gmail-supported email service in a non-gmail domain. Between FEB 28 2022 and May 30 2022 you may need to allow your account to use "less secure" programs such as Mail.app, and after May 30th you/we are out of luck. Here is what I found >> https://support.google.com/accounts/answer/6010255

They suggest that if you turn on two-factor authentication (2FA) or somehow use google authentication (which I think requires logging in on a browser page), you can continue to use Mail.app, but I don't see that option in any settings on my Mac. Mail.app only gives me the option of name+password.

1) Google does say they will turn off the "Less secure" option if not used for some time. That might be pretty short. However, mine still works 14+ hours after allowing less secure apps. I have two gmail-supported accounts and it was very clear that the problem was solved as I turned that option on one account at a time. One is an actual gmail account and the other is an academic gmail-supported account in an EDU domain. Both were failing, and both now work in the "less secure" fashion.

2) Wondering how Apple is going to solve this. They can't just say "Don't use gmail." Perhaps the OS 12 upgrade solves it. I will not know until after all music software is certified for use on Mac OS 12.x.

BTW, I did turn on the "less secure" choice in my gmail-hosted account and suddenly Mail.app worked again, so this is clearly the problem I was facing. But May 30th this apparently will stop working.