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Recent Gmail/Outlook sync broken. 0 Recommended Answers 125 Replies 465 Upvotes
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Starting on Monday the 20th my Gmail stopped being able to sync with Outlook.  I have seen on other boards that this occurred starting on that day, but I haven't found any solutions posted yet.  I have reset the passwords, deleted the accounts and set them up again, and nothing works.  The change to the setup is that it now prompts a pop-up to log into Gmail (like if you're using Gmail to log in to other sites), which it didn't do on previous setups.  Has anyone found a solution to this please?  It's very disruptive to my work having to swap back and forth between programs and constantly closing out that login box.   Thank you for any help you might be able to offer!
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So, Outlook is putting up a Google login screen?  If so, are you able to sign in successfully?
 
OR, do you mean that you are told to sign in and you need to load the browser to do so? 
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Yes, Outlook started putting up a Google login screen a few days ago.  I have tried logging in using both my normal Gmail password, and the app-specific one I've recreated a few times (and I use 2-step verification), it asks me to allow Microsoft to access mail and personal info, and it gives a failure message of "Sorry we are not able to sign you into Google - IMAP.  Please try again later."  It's a Google login screen pop-up like sites have for logging in with Google or Facebook instead of creating an account.

I am able to sign in directly through a browser with no issues, so this is something only related to the Outlook/Gmail link.
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It sounds like Outlook finally supports OAuth2.  Can we assume that you are giving it permission to access your account before it fails, or are you denying the access? 
 
(You will use your normal password and 2SV code to sign in, not your App Password.)
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I'm giving it access before it fails (though I tried Deny just to make absolutely sure).  It fails using my app password and my regular password, whether it's in the Outlook settings, or in the Google sign in box.  I've tried every combination of the two.  This is something that changed recently, as when I posted on the Outlook boards someone sent me a link to some other boards where people had seen a similar situation starting on Monday and no solutions were found (they weren't using 2SV, so I posted here).
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I just tried it and had no trouble adding a Gmail account to Outlook.  It did go through the OAuth2 login, then connected to my account.  That suggests that the problem is not on the Google side.  (Yes, the account has 2SV enabled.  I just entered my password, then the auth code and allowed access.)
 
Because you have tried this multiple times, I would suggest reviewing the connected apps in your Google security settings and remove any Microsoft entries, so you can start clean. (My account→Security→Third party apps with account access or https://myaccount.google.com/permissions).  
 
Did you ask for help from Microsoft? 
 
There may be a bug in Outlook when updating existing accounts.  Have you tried removing and re-adding the account in Outlook?  
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I've only tried the Microsoft help boards since I don't pay for a support subscription.  That's where I found that others started experiencing this same issue at the exact same time and in the exact same way, but no solutions were posted.

I have tried removing and re-adding the accounts and it still hits the same road block.

Google says no third-party apps have permission to access my account (weird since they've been linked to Outlook for many years), but I can't click on the area to add a third-party app to the permissions.
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I concur that Gmail and Outlook have been having issues since the 20th of May, 2019. I run an IT company and besides my own people having this issue, I've had over 20 calls complaining about the exact same issue. We are able to go all the way thru the "Add Account" dialog in Outlook 365, and regardless of using 2 factor, or an app password, and the end to the entire configuration exercise is: "Sorry, we could not sign you into Google - IMAP. Please try again later." This exists regardless if it is a manual inbound/outbound server config, or an attempt at an "express" configuration. Any help would be most appreciated.
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I have the same problem, @bkennelly the problem doesn't exist with new gmail accounts that configured for the first time, i setup a new gmail account in outlook365 (latest upate) and this works without problems, the problem exists with gmail accounts that are already configured in outlook365 and that worked fine untill that monday. I have 2 laptops, wich are more or less the same in setup and config, in one outlook i have no problems, and in the outlook installed from the same MS account on the other laptop the popup is generated every time outlook syncs, i cant imagine that this is a MS or outlook problem
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I am having the exact same problem and it just started with an office update a few days ago - has anyone figured out a solution?
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The Microsoft Outlook on my desktop stopped working.  I have a maintenance plan with Dell.  Yesterday they took remore control of my computer, uninstalled Outlook, and reinstalled it from the Microsoft website.  They then synched Outlook and Gmail.  Now I can only see mail in My Gmail Inbox from the time this process was completed yesterday.  I can't see any information about emails prior to yrsterday morning.  However, I CAN see all prior emails on my Outlook Inbox.
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