Outlook 2019 Randomly Disconnecting from Gmail Servers

[Korishan]

I have 2 gmail accounts connected to my Outlook 2019. Everything worked fine up to about 2-3 weeks ago. Randomly Outlook will stop being able to connect to my gmail accounts. I can restart Outlook without success. The ONLY fix is to reboot my computer and then Outlook will connect just fine. And then, after unknown amount of time, it will randomly stop connecting again and I have reboot, AGAIN, to fix the issue.
Creating a new PST/Profile does NOT fix the issue.
Deleting and re-adding the accounts does NOT fix the issue.
Doing a Repair on Office does NOT fix the issue.
Loading in Safe Mode does NOT fix the issue.
I am up to date on all updates for Outlook, which I even double checked again today to make sure it was updated (went to About and Check Updates). Windows Update also does no show any updates for Office 2019.
What is going on here and how to get this fixed?! Having to reboot my computer just to check my email is not very productive.

 

[Korishan]

well, apparently it's not *Outlook* directly. Must be some service it uses or something. I rebooted my system and didn't reload Outlook immediately. Been about an hour. I loaded it up, and it won't connect to the gmail server.

 

[Diane Poremsky]

Any error messages?

 

[Korishan]

The only error that shows up is this:

Task 'Synchronizing subscribed folders for ***@gmail.com.' reported error (0x800CCC0E) : 'Outlook cannot synchronize subscribed folders for ***gmail.com. Error: Cannot connect to the server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'

Which isn't very helpful, considering it works right after a reboot, but waiting awhile it stops.

 

[Korishan]

Randomly, for some unknown reason, it started working just fine. I have no idea what happened.

 

[Korishan]

oh wonderful! Now it's not checking/sending my xfinity/comcast account!!! !?!?!!??

 

[Korishan]

Oh this is freakin frustrating. Just did a "Security Update" yesterday, and now it stops checking the gmail accounts again!!
I reboot, load up Outlook, and it works for a few times. Then stops checking the gmail accounts. WTH!?!?!?

 

[Korishan]

Wanting to do an update to this. I'm beginning to think that it is "not" Outlook or MS in this particular case.
On my mobile phone I use a client called Edison Email. Over the past couple days I got 'notifications' of new email in my gmail account. But when I open the application up to view them within the app, there is no email listed. Today is 9:50pm Thursday. The last email I have listed is from 12:52pm Tuesday. Even doing a forced refresh won't update the mail listings.
However, if I go to mail.google.com there's all the emails from the past couple days shown clearly.
So apparently there is an issue with Google Email Services.

 

[Diane Poremsky]

Have you logged into gmail.com to look for security messages?

If you are not using 2-step authentication, Google will disable 'allow less secure apps' and often post a message asking if the sign in attempt was you.

Otherwise, yeah, it could be a general google issue. But log into Gmail to verify it's not google blocking you.