Dear Mike_884
Welcome to Microsoft Community.
According to your description, you are having problems with Gmail mailboxes joined using IMAP within 365 Outlook Classic.
Based on your description, I suggest you try to refer to the following process to try to operate to see if it can solve your problem:
You can remove Gmail access from Microsoft apps and services as follows and then do a browser login from Outlook again. The following steps enable you to go back to browser login where you can check the checkbox.
Step 1: Remove access for Microsoft Apps & Services in Gmail.
-Close Outlook.
-Sign in to your Google account on google.com.
-Select your profile picture in the top corner and select Manage your Google Account.
-On the left side menu, select Security.
-Scroll down to Your connections to third-party apps & services and select Microsoft apps & services.
-Locate Microsoft apps & services has some access to your Google Account and select See Details.
-Under Access you’ve given to Microsoft apps & services, select Remove all access.
-Select Confirm.
Step 2: Delete the Google IMAP credentials from Windows Credential Manager
-From the Windows Start menu, search for Credential Manager and open it. On Windows 10 you may need to open the Control Panel to access Credential Manager. For more information, please go to Accessing Credential Manager.
-Under Manage your credentials, select Windows Credentials.
-Scroll down to Generic credentials and locate those starting with MicrosoftOffice16_Data:OAUTH2.
-Expand each of these and hover over MicrosoftOffice16_Data:OAUTH2 until it shows the full name including the tp_google_imap_Oauth2. These are the Google credentials for your Gmail account.
-Select Remove for each of these with the MicrosoftOffice16_Data:OAUTH2. If you have multiple Gmail accounts, you will need to sign in to each of them again.
1.If you want to avoid removing Google IMAP credentials except for the specific affected account, you can map the credentials by comparing them to the identities in this registry key below. Open Registry Editor and paste this path in the Address bar at the top.
Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity\Identities
Disclaimer: Generally, modifying registry subkeys or work group is intended for advanced users, administrators, and IT Professionals. It can help fix some problems, **however, serious problems might occur if you modify the registry incorrectly. Therefore, make sure that you follow these steps carefully. For further protection, back up the registry before you modify it. Then, you can restore the registry if a problem occurs.**For more information about how to back up and restore the registry, click How to back up and restore the registry in Windows - Microsoft Support to view the article.
2.The sub keys to this registry key above include your Gmail identity. At the beginning of the identity registry key is a number that matches your Gmail credential in Credential Manager. See the examples below for reference.


-After you have done the steps above you are now ready to Sign in via browser from Outlook. Open Outlook to the Outlook profile that was not syncing and select the Sign in via browser business bar in Outlook. Make sure during browser sign in to check the box for Microsoft apps & services noted at the top of this article.
If you removed the Gmail account from your Outlook profile, select File, Add account to add the Gmail account back again and do the browser sign in process again.
You can also see the link:Unable to add a Gmail account to classic Outlook - Microsoft Support
Please also note that if the above methods do not solve your problem, you can only contact Microsoft support manually and have it handled by the other party's access through the following methods:
1.Click the link.–Contact - Microsoft Support
- In the box under “We're here to help,” enter Outlook, click Get Directions, and then click Contact Customer Service. (You must be logged into your Microsoft account. If not, follow step )
- In this section, you need to sign in to your personal Microsoft account.
Note: You can only sign in with your personal MSA, when you sign in with your company account, it will not display correctly. If you are unable to connect to this account, you can use another account or create a new account to manage it.
- Under “Products and Services”, select “Other Products”, select “Outlook”, and then click Confirm.
- You can select “Chat with a Support Specialist in a Web Browser” and go to the chat window.
Note: Please contact us during local business hours on weekdays, CHAT is not available 24 hours a day.
Feel free to text back if you need further help.
Best wishes
Chris.S-MSFT | Microsoft Community Support Specialist