Gmail account won't connect on early 2015 MacBook Pro

This question has cropped up multiple times here, but no solution that I saw proposed has worked.


My son's early 2015 MacBook Pro is running Sierra 10.12.6. Software updates list no newer compatible OS, and it was updated Jan 1 2019 (security update). He is logged in to his usual Gmail account on Mail app, and in Chrome browser, no problems. He has a second gmail account, which is through a university. This account suddenly won't connect on his laptop. We get the ""Connection insecure"/"failed to verify the server certificate" error when we deleted the account and try to re-install it in Internet Accounts. Pertinent info:

1) The account works normally on the same laptop when he logs into it via Google Chrome.

2) The account works normally on his iPhone.

3) The account works normally on my MacBook Pro (running Mojave 10.14.2).

4) He was required to change his password for this account recently (new semester).

5) Restarting his laptop with and without antivirus (Bitdefender) had no effect.

6) Keychain was reviewed thoroughly, and there were two expired (red x) certificates that were not related to gmail. Both were deleted, laptop restarted; no effect.


Any help would be appreciated.

Macbook (2015 or later)

Posted on Jan 7, 2019 3:24 PM

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Posted on Jan 10, 2019 8:02 AM

Update: It took a while, but Mojave is now running on my son's laptop (the early 2015 MacBook Pro). In order to install Mojave, he had to first install High Sierra, followed by a High Sierra update that crashed a few times during download. I clicked "More" in that update in the App Store, and saw that it was two updates bundled: an OS update and a security patch. I successfully dl'd the update alone, and then tried the security patch...which crashed. So, I took a chance on trying Mojave without the High Sierra security patch, and it worked.


Due to the crashes, I did uninstall Bitdefender completely from his laptop, and turned off his parental controls on my laptop, before installing Mojave. I had hoped to address one variable at a time and hold off on deleting Bitdefender. but at this point, I was getting impatient, so I uninstalled it before dl'ing Mojave.


The college gmail account then installed with his new account PW, and is working fine.


I am using OpenDNS to block his most common daylight time wasters, but it doesn't give device-specific controls like Bitdefender does. I will probably try to reinstall Bitdefender in a couple of days, and see how it goes. I will give you an update after that.


Thank you again, Eric! You're Level 10 status is deserved. :-)

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Question marked as Top-ranking reply

Jan 10, 2019 8:02 AM in response to Eric Root

Update: It took a while, but Mojave is now running on my son's laptop (the early 2015 MacBook Pro). In order to install Mojave, he had to first install High Sierra, followed by a High Sierra update that crashed a few times during download. I clicked "More" in that update in the App Store, and saw that it was two updates bundled: an OS update and a security patch. I successfully dl'd the update alone, and then tried the security patch...which crashed. So, I took a chance on trying Mojave without the High Sierra security patch, and it worked.


Due to the crashes, I did uninstall Bitdefender completely from his laptop, and turned off his parental controls on my laptop, before installing Mojave. I had hoped to address one variable at a time and hold off on deleting Bitdefender. but at this point, I was getting impatient, so I uninstalled it before dl'ing Mojave.


The college gmail account then installed with his new account PW, and is working fine.


I am using OpenDNS to block his most common daylight time wasters, but it doesn't give device-specific controls like Bitdefender does. I will probably try to reinstall Bitdefender in a couple of days, and see how it goes. I will give you an update after that.


Thank you again, Eric! You're Level 10 status is deserved. :-)

Jan 8, 2019 10:50 AM in response to Eric Root

Thank you! I will get to work on that, and report back.


I did first check his OS version for updates, and was mystified as to why his early 2015 MacBook Pro wouldn't show any macOS update beyond Sierra, while my mid 2015 MacBook Pro is running Mojave. Like most teens, he is quite adept at ignoring non-automatic update notices...


So I will start with Mojave and see what happens. I did look for that first, but as you indicated, it isn't obvious how to do it now that he has missed the initial launch install window.


I am using Bitdefender for multiple reasons, after researching my options. One of them is parental controls of devices (although the troublesome email is a college account, my son is a teen at home using dual enrollment). I turned off Bitdefender on his device, and on mine (parental controls), but I did not completely uninstall it. No similar problems in the rest of the house, including two iPads, three laptops and three iPhones. Just this one account on this one laptop.

Jan 8, 2019 10:25 AM in response to tj_610

If the computer is a MacBook 2015 or later as your profile shows, it can be upgraded to Mojave. Upgrades do not show in the App Store Update tab. He would need to go to the App Store Featured tab and download Mojave from there. For the Gmail problem, see if this helps. Below that, I'll list some troubleshooting steps and then upgrade information. I would uninstall Bitdefender. It tends to interfere with the computer's operation while providing minimal to no benefit unless you work with Windows files. Most long time posters recommend not using antivirus software or cleaning software such as CleanMyMac. They can adversely affect normal computer operation.


Google - let less secure apps use your account



Bitdefender uninstall


Try setting up another admin user account to see if the same problem continues. Please post back on whether or not this worked. Also try the Safe Mode. Please post back on whether or not this worked.


Isolating an issue by using another user account 


Safe Mode - About


If it works in the Safe Mode, try running this program when booted normally and then copy and paste the output in a reply. The program was created by Etresoft, a frequent contributor.  Please use copy and paste as screen shots can be hard to read. Click “Share Report” button in the toolbar, select “Copy to Clipboard” and then paste into a reply. This will show what is running on your computer. No personal information is shown.

  

Etrecheck – System Information


If the log won’t post, try posting it in Pastebin and provide a link in a reply        Pastebin


How to upgrade to macOS Mojave - Apple Support


How to get macOS High Sierra   


Check to make sure your applications are compatible.



 Application Compatibility



Also check to make sure there is a compatible driver for your printer.




Do a backup before installing, preferable 2 backups on 2 different drives.









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Gmail account won't connect on early 2015 MacBook Pro

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