Hi Brent Ford,
Welcome to Microsoft Q&A.
It sounds like this may be related to a Google OAuth sign‑in or permission issue between Classic Outlook for Windows and Gmail, which can occur if the Google authorization flow doesn’t complete correctly.
Since you’ve already confirmed that IMAP is enabled in Gmail, please try the steps below to refresh the connection:
1. Clear old Outlook credentials (if present)
Close Outlook. Open Windows Credential Manager > Windows Credentials.
Under Generic Credentials, remove any entries starting with: MicrosoftOffice16_Data:OAUTH2 that reference Google.
2. Remove Outlook’s access from your Google account
Sign in to Gmail using a web browser.
Go to Google Account > Security > Third‑party apps with account access, locate Microsoft apps & services, and select Remove Access.
3. Add the Gmail account again and confirm all permissions
Open Outlook and go to File > Add Account.
When the Google sign‑in page appears, expand the permissions and make sure the option allowing Outlook to “Read, compose, send, and permanently delete all your email from Gmail” is checked. If this permission isn’t granted, the IMAP setup can fail.
Tip: If Outlook shows an error window with a Retry link, select Retry. This often reopens the correct Google sign‑in page and allows the permissions to be confirmed properly.
Microsoft has also documented this behavior and the same remediation steps in the following support article, in case you’d like to reference it: Unable to add a Gmail account to classic Outlook
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.
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