Mac Mail not syncing to Gmail server

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Mac Mail not syncing to Gmail server

I have a MacBook Air running Mojave 10.14.6. Suddenly, as of a few days ago, actions I take within the Mac Mail client are not reflected on the Gmail server, and consequently don't get communicated to the mail app on my iPhone 8. New email comes in to both apps just fine, but email that I read or delete within Mac Mail does not show as read or deleted in the webmail interface for the Gmail account, and consequently shows the same on the iPhone. At first I thought this was a problem with the phone, since it coincidentally started right after updating to iOS 14.2, but it's now clear that's not the case.

Is there any point in my opening up an Apple Support ticket for this? Is this more likely to be an issue specific to me, and thus perhaps solvable by removing and re-connecting the account in Mac Mail? Or is this more likely to be on their end, just one of those periodic ******* contests between tech titans and their servers that will eventually work itself out?

MacBook Air 11″, 10.14

Posted on Nov 30, 2020 11:35 AM

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Answer 1

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Tesserax

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151,601 points

Nov 30, 2020 12:02 PM in response to bratsche59

bratsche59 wrote:

Is there any point in my opening up an Apple Support ticket for this? Is this more likely to be an issue specific to me, and thus perhaps solvable by removing and re-connecting the account in Mac Mail?

I would suggest that you completely remove, and then, re-add back your Gmail account in the Apple Mail app to see if this resolves the issue.

Additionally, if there is anything amiss with your Google account credentials they may show up by using the Mail Connection Doctor.

Ref:

Use Mail Connection Doctor in Mail on Mac - Apple Support
Troubleshoot email problems in Mail on Mac - Apple Support

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Answer 2

bratsche59 Author

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Nov 30, 2020 12:07 PM in response to bratsche59

Changes that I make in the iPhone Mail app *do* get received by the Gmail server; if I delete an email on the phone, it disappears from Mac Mail within a second or two. So the issue is only with information not going upstream from Mac Mail to Gmail.

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Answer 3

bratsche59 Author

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Dec 1, 2020 9:28 AM in response to Tesserax

Thanks so much for all these suggestions. I think the issue is now resolved! I followed a suggestion to "flip the switch" on the email account that I found here: https://michaelkummer.com/tech/fix-email-problems/ way down in Additional Email Troubleshooting. Basically it boiled down to this: with the Mail app open, go to System Preferences > Internet Accounts, choose Google from the list at the left, uncheck the box for Mail; quit Mail; re-check the box; re-launch Mail. Since doing that, everything is behaving as it should. That list at the "Edit Server Settings" place is still empty, but I'm not going to lose any sleep over it. Many, many thanks again for the assistance, and I've bookmarked all the resources you provided for next time.

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Answer 4

Tesserax

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151,601 points

Nov 30, 2020 7:35 PM in response to bratsche59

Apple provides the following link to obtain the correct email server settings for just about any email account. I suggest starting there to find out the correct servers to use for Gmail.

Ref: Mail Settings Lookup - Apple Support

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Answer 5

Tesserax

Level 10

151,601 points

Nov 30, 2020 12:49 PM in response to bratsche59

bratsche59 wrote:

Changes that I make in the iPhone Mail app *do* get received by the Gmail server; if I delete an email on the phone, it disappears from Mac Mail within a second or two. So the issue is only with information not going upstream from Mac Mail to Gmail.

This would appear to indicate an issue with having the correct Gmail SMTP server setting. Regardless, do understand that Apple Mail attempts to "duplicate" the email server mail folders that it finds. Since Google uses a propriety email folder structure, it can sometimes get a bit "screwy" on what Apple Mail thinks is a mailbox. Unfortunately, this is somewhat common with GMail.

The following two articles may help shed some light on what I am referring to:

Set Up a Gmail Account Using the Mac's Mail Application - Lifewire
Gmail vs Apple Mail: Which is Better? - EmailAnalytics

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Answer 6

bratsche59 Author

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Nov 30, 2020 12:12 PM in response to Tesserax

Thanks; it's seeming like I may have to do that. It seems unlikely to be an issue with credentials, because new email is coming in to both Mac Mail and iPhone Mail apps just fine, and I've just established that if I delete an email in the iPhone Mail app, that info is going upstream to the server and then being reflected in Mac Mail pretty much immediately. There is only a problem going upstream from Mac Mail to the server.

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Answer 7

bratsche59 Author

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Nov 30, 2020 1:38 PM in response to Tesserax

Tesserax wrote:

This would appear to indicate an issue with having the correct Gmail SMTP server setting.

Okeydokey, when I drill down in Mail to "Edit SMTP Server Settings," what should be a list of servers is empty. I'm guessing this is a problem...

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Answer 8

Tesserax

Level 10

151,601 points

Dec 1, 2020 9:56 AM in response to bratsche59

Excellent! I'm glad you got it worked out ... and thanks for the link as I'm sure it will help others should they come across the same issue as you had.

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Mac Mail not syncing to Gmail server

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