Cannot get Apple mail to accept passwords for Gmail on MacPro

Question

Cannot get Apple mail to accept passwords for Gmail on MacPro

I am running 10.13.3 on a mid-2012 Mac Pro. I cannot get Apple Mail to accept any passwords for Gmail. I have no issue with my iPad, iPhone or on the web. I do not have 2-step verification turned on with any of my devices or with Gmail. Yesterday, for a few hours, mail was working, then it was back to endless attempts to enter passwords for my two Gmail accounts. I should point out that I was having the same problem with my iCloud account but that mysteriously started working and is still working. I have tried to add a Proton Mail account with the same results as the Gmail accounts. Both Gmail accounts are configured to be IMAP.

I have owned dozens of Macs through the years starting with the Mac Plus but since my extended warranty has run out on this machine, no one at Apple will talk to me. I "think" that the problem began with the 10.13.3 update but that belies the fact that both were working for a while yesterday.

Please, someone put me out of my misery with a good answer.

Posted on Mar 22, 2018 4:03 PM

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Answer 1

Top-ranking reply

Grant Bennet-Alder

Level 10

140,921 points

Mar 23, 2018 8:17 AM in response to tygb

If you set it up again, this time using Internet Accounts, use the "Google" special case provided. This allows gmail to convert your password into a token-and-certificate rather than a simple password.

You may have to delete your account information and re-enter it. Nothing should be lost in doing this.

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Answer 2

Mar 23, 2018 4:56 AM in response to Grant Bennet-Alder

My MacBook Pro mid-2012, 2.5 Ghz Intel Core i5, is running OS 10.13.2, accepts my password without a problem and sends and receives mail normally. This has nothing to with Google or Proton Mail not waking up to deliver mail. I am more convinced than ever that this is an Apple problem with OS 10.13.3.

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Answer 3

Mar 23, 2018 5:24 AM in response to tygb

No problems with iCloud on any devices. My iCloud address is not an issue, I do know the differences. I do not use any Apple base stations and I connect to the internet via AirPort. I have not changed any settings regarding date or time or anything else. I don't use a Shared Folder since I do not network my MacPro, I can logon iCloud, iTunes, and the App Store without a problem. My Apple ID is the same as my main email accounts. I'll look at my KeyChain but I am doubtful since it has been working properly with everything else.

But thanks for the suggestions.

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Answer 4

tygb

Level 9

65,010 points

Mar 23, 2018 5:43 AM in response to robert.stevens

When you open mail application , click on mail on top menu bar > add account and follow the upcoming steps like entering your gmail address and password , do you see an empty rectangular box and small circle is rotating continuously , what is the connection doctor status .

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Answer 5

Mar 23, 2018 8:55 AM in response to robert.stevens

Ok, here's what worked. I was getting that tilde-like character next to my Gmail accounts indicating that the accounts were not online. Nonetheless, I went to one of the accounts and composed a message to the other account and sent it. I almost fell out of my chair when I head the whoosh of a transmitted email. Sure enough, the email appeared in my other account followed shortly by 300 or 400 hundred other emails, most into the spam folder.

I want to thank all those that took the time and made the effort to reply to my post for help. I still have no idea what caused the problem nor why this seemed to fix it but I am very relieved that it seems to have disappeared.

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Answer 6

Mar 22, 2018 6:55 PM in response to robert.stevens

Some email providers do not place a high priority on their Servers being available 24/7. Many operators freely take their mail servers offline for backups and service without notifying or compensating you.

Mac Mail has only one thing it can do when a mail server does not respond. That is the same thing it does 3 seconds after initial setup. It asks you to try re-enterinig your password again. Almost always, this is not helpful. In some cases, it destroys your perfectly valid password and leaves you with NONE.

If your mail has been running for a while, and you know the password has been good, just dismiss the box asking for the password and try again later. When the Mail Server is back up and running, it will connect just fine.

For increased Visibility, use:

Mail > Window > Connection Doctor ...

... to get a one-page display of the status of each sending or receiving Server. Sometimes you will see status that tells you more about what is really going on.

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Answer 7

tygb

Level 9

65,010 points

Mar 22, 2018 10:24 PM in response to robert.stevens

See this article If you enter your iCloud Security Code incorrectly too many times - Apple Support

Once the iCloud Keychain is set up , open system preferences > internet accounts > enter the gmail address and password and iCloud id and password to configure , then check the connection doctor .

Some questions - do you changed date and time settings in system preferences , changed read and write permissions in shared , home folder or guest account ? Do you have " iCloud security code " trusted device ie mobile , all Apple ID , iCloud address and passwords , are you having wireless network or base station password with you , is your Mac configured with air port utility or only using ISP router .

Can you sign on iCloud server ( www.icloud.com) with your Apple ID , also on appleid.apple.com , in iTunes , apps store using your gmail id ie Apple ID .

Generally Apple ID is kept same as gmail address .

As these problems will be created and possibilities are system keychain is corrupted .

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Cannot get Apple mail to accept passwords for Gmail on MacPro

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