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JPG file attachment issues on Mac with recent Outlook updates

Mary Helen 20 Reputation points
2025-11-06T13:39:16.6366667+00:00

I NEED to be able to attach JPGs as file attachments with drag & drop from Mac (Sequoia 15.7.1) to Outlook (16.102.3). However, Outlook is only allowing JPGs to embed into the body of the email. Even when dragging attachments directly from one email to another.... the JPGs only embed into the body since the most recent Outlook update.

I'm a graphic designer who needs to be able to provide art files without them embedding in the email body.

This has been going on for months since the recent set of Outlook updates. Please tell me there is a way to make drag & drop JPG file attachments possible. It is EXTREMELY slow to have to go through the "Attachment" menu and navigate manually to the needed files.

Any advice on this would be appreciated.

Outlook | MacOS | New Outlook for Mac | For business
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  1. Michelle-N 9,260 Reputation points Microsoft External Staff Moderator
    2025-11-06T14:13:52.9333333+00:00

    Hi @Mary Helen

    Thank you so much for contacting Microsoft Q&A Forum. 

    Based on what you've shared, I understand your problem perfectly. You're on Outlook for Mac, and when you drag and drop a JPG file, it embeds directly into the body of the email. As a graphic designer, you need it to attach as a file, and this problem has been happening since a recent update.

    I've tested this on my environment, and you're right: if I drag and drop a JPG file into the main content area, it embeds it instead of attaching it.

    However, I did some testing and found a workaround you can try:

    Try dragging and dropping the JPG file directly onto the "Subject" line (the subject text box), like I've highlighted in the image below.

    User's image

    In my environment, when I do this, it successfully adds the JPG as a file attachment, as you can see in this second image.

    User's image

    Please give that a try and let me know if it works for you.

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  1. Mary Helen 20 Reputation points
    2025-11-11T18:20:33.9133333+00:00

    While I'm accepting the answer as a temporary fix.... this means I cannot update Outlook past August 2025 until the subject area glitch is figured out for the Outlook app for Mac/Sequoia.

    Hopefully this is worked out soon, since failing to update regularly can be a security issue. :)

    Thanks for the help!

  2. Hornblower409 2,680 Reputation points
    2025-12-12T11:00:10.1133333+00:00

    You can vote for and comment on this Outlook Mac Feature Request.

    Drag images into email as attachments without embedding
    https://feedbackportal.microsoft.com/feedback/idea/bd5106b6-31d0-f011-ad8f-7c1e52f38cbc

    It used to be possible to drag images onto the subject or from/to box so they would be sent as attachments rather than embedded images. This function has been removed in new outlook and you have to manually navigate to the image via the ATTACH icon which is a much longer and laborious process

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