Outlook users getting error "Some of the files in this web page aren't in the expected location do you want to download them anyway?"

Erik Zimmerman 16 Reputation points
2026-09-16T16:28:26.56+00:00

We have had a couple of users getting this error with classic outlook in the last few days since getting a recent update (2608 16.0.20326.20072). Both users have a gmail account in addition to their 365 account and the errors stopped once the gmail account was removed. Has anyone else seen this issue? There were no signatures, stationary etc that would normally cause this issue. It appears to be having a gmail/imap account setup that is causing the problem?

Outlook | Windows | Classic Outlook for Windows | For business

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  1. Kai-L 19,420 Reputation points Microsoft External Staff Moderator
    2026-09-16T17:00:41.4933333+00:00

    Dear Erik,

    As a forum moderator, I am not able to inspect your tenant or the affected machines to diagnose and fix this directly. My role here is limited to general guidance you can apply from your side. Your testing points strongly at a regression involving classic Outlook build 16.0.20326.20072 combined with a Gmail or IMAP account, particularly since removing the Gmail account stops the prompt entirely. I have not seen this specific error documented as a known issue for that build, so at this stage it looks like something worth reporting rather than something with a published fix. To firm up the evidence, on one affected machine:

    Start Outlook in Safe Mode: press window + R > outlook.exe /safe to rule out add-ins.

    If the prompt remains, create a temporary Outlook profile containing:

    • Only the Microsoft 365 account
    • Then add the Gmail account and retest

    For reference: Create a profile in classic Outlook for Windows | Microsoft Support

    Note exactly when the prompt appears, whether at startup, when selecting the Gmail mailbox, when opening a specific message, or when composing or replying.

    Check how the Gmail account was added, through Google OAuth or manual IMAP configuration.

    If adding Gmail to a clean profile reproduces it immediately, that is strong evidence of an Outlook and Gmail interaction rather than corrupted signatures or stationery.

    If the Gmail mailbox is not urgently required in classic Outlook, remove it temporarily and use Gmail in a browser. Avoid changing registry security settings or automatically allowing the unexpected downloads.

    Because multiple users were affected shortly after the same update, I recommend that the Global Admin in your organization create a service request with Microsoft Support. A technical support engineer can perform a remote session to investigate the situation, verify the backend configurations, and run any necessary synchronization tools to resolve the problem. If the issue requires further attention, they can escalate it to a specialized team for deeper analysis. For detailed instructions on how to get support, please refer to Get support - Microsoft 365 admin. If you don't know who your IT administrator is, please refer to this article: How do I find my Microsoft 365 admin? - Microsoft Support 

    For additional assistance, use this link to find the appropriate contact number from your region: Contact Microsoft customer support | Microsoft Support 

    I truly hope you get your issue resolved swiftly. Please know that even though I can't directly intervene, directing you to the correct, specialized support is the most effective help I can provide from my position. I will leave this thread open in case other members are seeing the same thing on that build. Thank you for your patience and understanding. Please let me know if you need anything else. Wishing you all the best. 


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