Issues with Outlook syncing with GMAIL

Question

Issues with Outlook syncing with GMAIL

Pinterest123 0

My company uses Gmail (Google Workspace) for email, and I've funneled it through legacy Outlook for Mac successfully for ~4.5 years. As of Friday, August 14, 2026, something changed and Outlook on my Mac no longer fully syncs with Gmail.

What still works:

Sending and receiving email in Outlook works normally.

What's broken:

When I delete, file, or move a message in Outlook on my Mac, the change does not propagate back to Gmail — the email stays put in the Gmail inbox/folders. My calendar is also no longer syncing properly. Notably, there are no sync errors and no sync-status warnings shown anywhere in Outlook — the app behaves as if everything is fine.

The Outlook app on my iPhone syncs perfectly — changes I make there appear in Gmail immediately. So the problem appears isolated to the Mac desktop client's ability to push local changes back to the server (incoming/download works, outgoing/write-back does not). Account, credentials, and Google-side settings all seem healthy given the phone works.

Environment:

Device: MacBook Air

macOS version: Tahoe 26.6.2
Outlook for Mac (legacy) version/build: 16.112.1 (26081720)
Account type: Gmail / Google Workspace

Connection: on a corporate VPN when using the Mac

What I've already tried (nothing has held):

Updated macOS and the Outlook app to the latest versions Fully signed out on all devices and re-logged in (multiple times) Cleared cache and deleted Keychain entries for Outlook/Gmail Uninstalled and reinstalled the Outlook app entirely Switched to New Outlook for Mac and tried from there Switched to New Outlook and then reverted back to legacy Verified all Gmail IMAP settings (IMAP enabled, Auto-Expunge / "move to Trash" options) and Outlook settings, and checked all sync-status/error indicators Deleting and re-adding the Gmail account on the Mac — this works for a few hours, then the same issue returns

The recurring pattern is: re-add the account → syncs correctly for a few hours → silently stops pushing changes back to Gmail (and calendar) again, with no error shown.

My questions:

Is this a known bug Microsoft is aware of (especially anything introduced around mid-August 2026)? Is a fix in progress, or is there a recommended workaround for legacy Outlook for Mac + Gmail specifically? Given legacy Outlook for Mac's end-of-support timeline, is there a supported configuration that resolves write-back sync reliably?

Any guidance appreciated — thank you!

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1 answer

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Answer 1

Elena-VH 1,325 Independent Advisor

Dear @Pinterest123

Thank you for the detailed troubleshooting summary, and I see that you've already completed most of the standard remediation steps.

Please note that Legacy Outlook for Mac is being phased out and will only receive security updates through October 9, 2029. Technical support is provided on a best-effort basis, and Legacy Outlook is no longer included in current Microsoft 365 for Mac subscription offerings. The legacy Outlook for Mac client will continue to work against Exchange On-Premises mailboxes until October 9, 2029.

For that reason, while Microsoft can continue troubleshooting, they may have limited ability to address issues that are specific to the Legacy Outlook experience. And users are encouraged to switch to the new version of Outlook for Mac, which offers improved performance and features. For reference: End of support for legacy Outlook for Mac

Since you've already performed most of the standard troubleshooting steps, I'd like to gather a few additional details:

1/ Are other users in your organization experiencing the same behavior?

2/ Have you tested using a different network connection? As a troubleshooting step, please disconnect from the VPN and test using another connection, such as a home network or a mobile hotspot (5G).

3/ As a final isolation step, create a new macOS user profile

Create a brand-new local macOS user account > sign in to the new profile.
Install Outlook and add only the affected Google Workspace account.
For reference, please see: Add a user or group on Mac and Set up local macOS accounts

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I hope the information shared is helpful. If you have any questions or if I have misunderstood anything, please feel free to reach out. I'm looking forward to your update.

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Pinterest123 0 Reputation points

2026-08-21T12:56:19.46+00:00
I've even tried using the "new outlook" and the same issue persists. Also, let the record show that new outlook doesn't function nearly as well as the legacy outlook, which is why so many people want to continue using the older version.

I don't know if anyone else in my organization is experiencing the same issue, Many of my coworkers have only used GMAIL for work, and therefore didn't seek alternate email mapping options. I prefer the functionality / visual formatting of outlook. I've also tried this on/off VPN, and on different WiFi networks.

I can't create a new macOS profile on my work computer.
Elena-VH 1,325 Reputation points Independent Advisor

2026-08-22T06:34:50+00:00

Dear @Pinterest123

Since you've already tested both Legacy Outlook and New Outlook, and you've also reproduced the issue across different networks and with the VPN disconnected

In this case, I recommend testing from a different device and checking again.

Additionally, do you have any Microsoft subscription associated with this Outlook installation?

If the issue persists, I would recommend reaching out to your organization's IT or helpdesk for further assistance. Work with your organization's IT team to see whether they can perform the new macOS profile test on a managed device or review any policies that may affect Outlook's interaction with Google Workspace.
Tony Wilkinson 5 Reputation points

2026-08-27T05:24:52.1533333+00:00

I have the same issue with Outlook for Mac. I switched between legacy and current version and the issue has continued to surface. I am able to re-establish synch to gmail calendar by removing the account from Outlook Mac then re-adding and authenticating into google mail/calendar. This reestablishes the sharing rights (note that just resetting the account does not work). The key piece appears to be that the authentication to google needs to be completely removed and re-established

The issue is that this keeps breaking every 1-2 days and after doing this continually for the last 2 weeks I am about to find an alternative solution to Outlook (which is a great pity since I have always preferred it)

Can you identify how to create a solution to synching Outlook Mac with Google Calendar?
Hornblower409 14,425 Reputation points

2026-08-28T03:57:28.1433333+00:00

@Tony Wilkinson said

Can you identify how to create a solution to synching Outlook Mac with Google Calendar?

You will probably not get any help for your issue by adding to an existing post. I would suggest that you start a new thread using the "Ask a question" button at the top of this page to create a new Question and include the details for your specific problem. This provides much higher visibility to your issue than adding on to an existing post, which is only seen by people who are already following this question.

(You can put the link for this page in your new Question for reference)
Elena-VH 1,325 Reputation points Independent Advisor

2026-08-28T04:47:38.1266667+00:00

Dear @Tony Wilkinson

Thank you for sharing your experience and the troubleshooting you've already performed.

If the issue continues to recur every 1-2 days, it may require further investigation specific to your Outlook, macOS, and Google account configuration. Therefore, I would strongly recommend that you start a new thread using the "Ask a question" button at the top of this page and provide the full details of your specific scenario.

Creating a new question gives your issue much greater visibility and allows community members and Microsoft moderators to focus specifically on your case.

Moreover, according to my research, there are several alternative methods available to connect Outlook Calendar with Google Calendar, which may be worth exploring if the current integration remains unstable. For reference: How to Connect Outlook Calendar With Google Calendar

Disclaimer: This link is shared by community members for your convenience. It points to a third-party site that is not managed or verified by Microsoft. We can’t guarantee the quality, safety, or suitability of any content or software found there. Please review carefully and make sure you understand any potential risks before using it.