Attachments disappearing after I reply to an email

Abby Demoss 0 Reputation points
2026-07-24T21:32:31.3766667+00:00

This is a new issue for me. In the last few days emails that originally had attachments with them are losing the attachments after I respond. I can't find them anywhere in my inbox or sent folder. It's incredibly annoying. I tried the changing my grouping setting but still did not work. What can I do.

Outlook | Windows | New Outlook for Windows | For business
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  1. Jay Tr 14,310 Reputation points Microsoft External Staff Moderator
    2026-07-24T22:32:04.46+00:00

    Hi Abby,

    Thank you for reaching out and for letting me know what you have already tried.

    To better understand a bit more about what is happening before suggesting a fix., please help me with the following:

    1. Does this happen with every email that had an attachment, or only with certain ones (for example, from specific senders or with certain file types)?
    2. When you reply and the attachment disappears, are you viewing the conversation with messages grouped together, or as individual messages?
    3. Is the attachment missing only from your reply, or is it also gone from the original message that first arrived with the file?
    4. Does the same thing happen when you open the mailbox in Outlook on the web using a browser?

    Thank you for your time and patience during the process. I'm looking forward to your response.


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