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

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Level 1

4 points

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

In the past few days, I have been blocked by google from sending emails from Apple's mail app on all my devices. I use a gmail email address. I receive this message: "The sender address was rejected by the server smtp.gmail.com. The server response was: Authentication Required." Apparently Google/Gmail has rolled out some new security measure that will no longer let me send emails using Apple's mail app. Reading google's instructions about how to rectify this makes absolutely no sense to me.

I have a MacBook Pro, early 2015 (yes, it's "old" but works just fine) and I'm running macOS Big Sur (I haven't yet made the plunge to update the OS.

Can anyone help me with this?

MacBook Pro 13″, macOS 11.6

Posted on Mar 6, 2022 3:15 PM

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Answer 1

Best reply

Jack-19

Level 8

45,716 points

Mar 6, 2022 9:09 PM in response to SPFischer

Welcome to the Apple Support Communities.

See:

If the issue persists, Upgrade to macOS Monterey - Official Apple Support, and try again.

Jack

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Answer 2

Jim Sky

Level 1

4 points

Mar 9, 2022 8:56 PM in response to SPFischer

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.

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Answer 3

SPFischer Author

Level 1

4 points

Mar 10, 2022 9:12 AM in response to Jim Sky

Well, after trying all the steps you tried, Jim, including using Google Authenticator, changing passwords, and turning on less secure choice, I finally threw in the towel. Last night, I was finally able to send from my account but this morning, the same irritating message popped up saying authentication required, which led down the same rabbit holes as before with no solution in sight. And strangely enough, I was still able to use Mail.app to send mail from another gmail account that I have but rarely use, so I figured my main email account was in some way corrupted. I deleted the account from my laptop and re-added it. Right now, everything is working as it should. I'm keeping my fingers crossed. But the May 30th deadline is looming and I still have no idea, like you, what that will mean going forward. Using webmail is a very clunky workaround. I'm praying Google and Apple find a way to work together on this and alert us to a solution. Thanks for chiming in!

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Answer 4

jimsky7

Level 1

12 points

Mar 10, 2022 9:44 AM in response to SPFischer

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.

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Answer 5

Jim Sky

Level 1

4 points

Mar 9, 2022 8:57 PM in response to Jim Sky

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.

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

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