Why is Outlook asking if I’m missing an attachment on every single email?

Austin Slisz 0 Reputation points
2025-10-06T19:40:41.54+00:00

Hello,

whether I am in the desktop app, web version or using the PWA, outlook always asks if I am missing an attachment. from what I understand, it is supposed to only prompt. If anything in the body of the email suggest there would be an email attached. It is happening in every form of Outlook on my computer so I don’t know where to start troubleshooting. The toggle in the settings, turns it off, leaving it on allows it to happen every time. Was there a change made to how this feature functions, if not, how would one fix it?

Outlook | Windows | New Outlook for Windows | For business
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Austin Slisz 0 Reputation points
2025-10-06T20:35:44.43+00:00

SOLVED! The company I work uses signatures that are editable in the email. New Outlook sees the word "attachments" in the signature and prompts the pop-up. However, Outlook Classic does not do this, probably one of the reasons why they still suggest classic for enterprise.

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  1. Anonymous
    2025-10-06T21:18:03.05+00:00

    Hi @Austin Slisz, 

    Thank you for posting your question in the Microsoft Q&A forum. 

    It's wonderful news that your issue has been resolved. I truly appreciate your effort in finding a resolution. I believe that many users may encounter similar issue, and your case could serve as a valuable reference for them.     

    Therefore, I would make a brief summary of this post so that other forum members could easily find useful information here:  

    Issue Description: New Outlook and Outlook keep prompting that the email is missing the attachment. 

    Assessment: Signature includes the word "attachments". Outlook’s newer versions include a feature that scans outgoing emails for phrases suggesting an attachment (e.g., “see attached,” “attachment included,” etc.). If such a phrase is detected but no file is attached, Outlook will prompt the user with a reminder - even if the word appears in the signature and not in the actual message body.

    Resolution: Edit the signature and remove the word "attachments" 

    Recommendation:  

    • Review and revise your email signature:
      • Remove or rephrase any mention of “attachments” unless it’s necessary.
      • Use alternative wording such as “documents” or “files” if needed.
    • Test your signature:
      • Send a test email without attachments and see if Outlook prompts you.
      • Adjust wording until the prompt no longer appears unnecessarily.

    As other users may search for similar issues in this forum, your post and solution will be a helpful reference. If you found this helpful, consider voting or marking it as a solution to make it easier for others to find.  

    We truly appreciate your time and cooperation throughout the resolution of this matter. Thank you for being a valued customer and for contacting us on the Microsoft Q&A forum.  

    If you need any other assistance, please don’t hesitate to reach out again and I would be happy to help you.  

    Wishing you a great day ahead.  


    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment". 

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