Mail on Mac will not connect to Gmail servers

Question

Mail on Mac will not connect to Gmail servers

A week or so ago Mail on my iMac stopped connecting to my Gmail servers. I have followed every single piece of advice/suggestion I can find on this community site and others to get back to normal but without success. Curiously, I can no longer even see outgoing and incoming server information on my mac and therefore have no settings to "change". I have no problem at all with Mail my iPhone and iPad. There must be a simple explanation for this - and, yes, I have checked everything on the Gmail end and the mac end. Any bright ideas?

My mac is a 27" late 2013 running macOS Catalina 1-.15.7 (which cannot be updated to Big Sur or Monterey) and Mail is version 13.4. Although I have had other issues recently (e.g. TimeMachine - which I have fixed, and inability to connect to a Sonos system - which I have not yet been able to fix), the mac works just fine apart from this new, out-of-the-blue mail failure.

iMac

Posted on Jul 10, 2022 6:46 PM

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Answer 1

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TheLittles

Level 10

195,657 points

Jul 10, 2022 9:48 PM in response to JazzLessOrdinary

JazzLessOrdinary Said:

"No matter how many times I turn the router off/on, wifi off/on and restart mac, still says connection failure, accounts remain offline and I cannot take the accounts online."

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Seems there is issues the the Mac's WiFi. So, refer to the following..

Troubleshooting Mac Wi-Fi:

A few thoughts to try...

I. Clear the Temporary Internet Files:

Cookies perform remembrance of certain site-entered data.
Cache keeps a snapshot of the last time you visited a site.
Go Here: Clear your browsing history in Safari on Mac - Apple Support

II. Restart your Router:

Power: off the router
Wait: 30 seconds
Power: It back on

III. Boot in Safe Mode:

In Safe Mode, Login Items do not run at login, certain preferences are set aside, and damaged system files are then reset. So, once booted in to Safe Mode, wait 30 seconds, and then boot up normally, attempting another update install. For instructions, go here: How to Use safe Mode on your Mac - Apple Support

IV. Try a New Admin User:

What happens when you create a new administrator user, and log into it? Do you still get this error? If not, then it is likely an error with the current user. If so, then it is likely an error with your Mac.

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Answer 2

TheLittles

Level 10

195,657 points

Jul 12, 2022 6:52 PM in response to JazzLessOrdinary

JazzLessOrdinary Said:

"Mail on Mac will not connect to Gmail servers: Thanks for the suggestion. It didn't work first time, so I removed again, did a little system cleaning with CleanMyMax X: TheLittles, you are a life saver. Really appreciate your taking the time to help me with my problem. Glad to see this support community works and there are people like you in it. Have a good one."

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You are welcome. And thank you for that compliment.

Two Next Steps:

1. Uninstall CleanMyMac X:

Next, I suggest that you uninstall CleanMyMac X. It is a utility to use, but is scam software, IMO. It has poor performance, and can damage your Mac, being it takes up lots of processing at times. Go here: How to uninstall CleanMyMac X - CleanMyMac

then...

2. Once installed, Back Up your Mac:

Back up your Mac with Time Machine, that way you can have something to restore your Mac from should anything go wrong from here one out.

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Answer 3

TheLittles

Level 10

195,657 points

Jul 12, 2022 9:18 PM in response to JazzLessOrdinary

JazzLessOrdinary Said:

"Mail on Mac will not connect to Gmail servers: Funny you should mention CleanMyMac X - I recently purchased a lifetime license and now wish I had not. To be fair, it did help in cleaning out a lot of stuff that was taking up memory and slowing my computer down, and a couple of other things that I could not do with the limited free version. We live and learn, eh?[...] Thanks again for everything."

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You are welcome.

Installing macOS Anew:

If you wanted, you could backup your Mac today with Time Machine, and then restore items as desired. This may be best rout, if you are uncertain which Time Machine Backup(s) would contain CleanMyMac X. As for the apps, you'd restore them from using Time Machine Backup, through use of Migration Assistant.

Getting Apps Back After a Restore:

If you have any issue with licensing, then contact the Developer of the software that is not transferring, letting them know that you restored your Mac from a backup, and that you need a new license key. All would would fine form there, I presume.

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Answer 4

TheLittles

Level 10

195,657 points

Jul 10, 2022 7:01 PM in response to JazzLessOrdinary

JazzLessOrdinary Said:

"Mail on Mac will not connect to Gmail servers: A week or so ago Mail on my iMac stopped connecting to my Gmail servers. [...]I have no problem at all with Mail my iPhone and iPad. There must be a simple explanation for this - and, yes, I have checked everything on the Gmail end and the mac end. Any bright ideas?[...]"

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Troubleshooting gmail:

Use a New App Password:

Do you use an App Password? If so, try a new App Password. Sometimes, changes (i.e. updates) are made to the device, and then mail server syncing becomes an issue (which is what a new App Password it intended to fix). Go here for gmail: Sign in with App Passwords - Google Account Help - Google

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Answer 5

Jul 10, 2022 8:59 PM in response to TheLittles

Thanks for this. No, I do not use an App Password. I sign in with Google and my normal passwords are correct at both ends. Funny thing is that when I open the “Mail” app on my Mac, select “Mail” → “Preferences…” → “Accounts”, and select my Google Account from the list, no password is shown, there is nowhere to input a password, and so I cannot replace the password even if I wanted to!

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Answer 6

TheLittles

Level 10

195,657 points

Jul 10, 2022 9:05 PM in response to JazzLessOrdinary

JazzLessOrdinary Said:

"Thanks for this. No, I do not use an App Password. I sign in with Google and my normal passwords are correct at both ends."

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Try an App Password:

Interesting it's not required. It might not be an option in the country where you are located. So, what happens when you try using an App Password? Its not showing up because there is no password. So, try entering you own password, or using an app password, as I just mentioned.

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Answer 7

Jul 10, 2022 9:37 PM in response to TheLittles

No way to enter own password or app password. My wife's mac is exactly the same as mine and what you see when you open Mail and follow the steps above is exactly what I see on my mac so I guess that's just the way it is (but she has no problems at all with mail on her mac). Curiouser and curiouser....

No matter how many times I turn the router off/on, wifi off/on and restart mac, still says connection failure, accounts remain offline and I cannot take the accounts online.

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Answer 8

Jul 11, 2022 10:02 PM in response to TheLittles

OK, so I went through your list and, lo and behold, the last item - try a new admin user - has moved things along. There were no mail problems at all when I logged in as the new user. The guidance notes say that this means software in my normal user account is the issue, or, expressed differently, the issue is related to my specific user setting or files. I would appreciate any further guidance you might have now that the issue has been (broadly) identified. Thanks again.

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Answer 9

TheLittles

Level 10

195,657 points

Jul 11, 2022 10:27 PM in response to JazzLessOrdinary

JazzLessOrdinary Said:

"Mail on Mac will not connect to Gmail servers: The guidance notes say that this means software in my normal user account is the issue, or, expressed differently, the issue is related to my specific user setting or files.[...]"

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Remove. then Add Account:

Remove the eMail from the Mail Account. Then, add it back.

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Answer 10

Jul 12, 2022 6:42 PM in response to TheLittles

Thanks for the suggestion. It didn't work first time, so I removed again, did a little system cleaning with CleanMyMax X, restarted the mac, then added the email again and Hey Presto! It worked. I have 4 different Gmail addresses, so added them one at a time and I think that helped too. TheLittles, you are a life saver. Really appreciate your taking the time to help me with my problem. Glad to see this support community works and there are people like you in it. Have a good one.

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Answer 11

Jul 12, 2022 8:08 PM in response to TheLittles

Funny you should mention CleanMyMac X - I recently purchased a lifetime license and now wish I had not. To be fair, it did help in cleaning out a lot of stuff that was taking up memory and slowing my computer down, and a couple of other things that I could not do with the limited free version. We live and learn, eh?

I use Time Machine already and glad that I do, for the reason you mention. I cannot remember whether it was before or after I started using CleanMyMac X, but my external hard disk drive on which I had been backing up with Time Machine suddenly would not work anymore (stuck on "Preparing back up") to the extent that the seemingly fine EHDD was not even recognised by my mac. Had to buy a new EHDD and start backing up all over again from scratch with Time Machine. Took a while but got there in the end. Now working just fine.

Thanks again for everything.

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