Since outlook for mac upgrade 16.102.3 I cannot drag files into emails in certain account

Gaye Miller 40 Reputation points
2025-11-04T22:38:22.9+00:00

Hi.

Since upgrading to 16.102.3 i now cannot drag files into my emails in certain accounts. Some accounts i can, others I cannot. The only option to insert an attachment is via the Attach a File option, but then you have to search your computer to find the file, rather than just dragging it over from a Finder folder.

Also, i now cannot set Calibri Light as my default font. The font settings are missing the options to select light, italics, bold, etc, like it used to in previous versions.

Is anyone having similar issues?

Outlook | MacOS | New Outlook for Mac | For home
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  1. Kimberly Olaño 17,395 Reputation points Independent Advisor
    2025-11-05T03:53:39.61+00:00

    That figures it. Your Exchange Online (Plan 1) mailbox still talks to Outlook using the older Exchange Web Services (EWS) protocol, and the new Mac client’s drag-and-drop handler is currently broken for that path in version 16.102.3.

    So while the hotfix is currently being worked on, make sure automatic updates is turned on. As for the drag and drop issue, use Attach File → Browse This Computer for that one account until the fix ships.

    OWA works normally, so that’s also a good temporary workaround.

    1 person found this answer helpful.
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  1. Kimberly Olaño 17,395 Reputation points Independent Advisor
    2025-11-04T23:18:40.7133333+00:00

    Thanks for sharing the details, Gaye! Okay you mentioned drag and drop still work for some accounts, so can you please check if the working vs non‐working accounts differ in type (e.g., Exchange vs IMAP vs Outlook.com) or if they are within “New Outlook” vs “Legacy Outlook” mode?

    For the font issue, it’s very likely a deliberate change in the new Outlook UI (or an un-fixed bug) that removed the ability to pick “Light” weight for Calibri as default.

    Because both issues arose after upgrading to 16.102.3, they may be part of the update’s regression or redesign.

    See if this helps. If you need further assistance just let me know.

    Best regards,

    Kimberly

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  1. Kimberly Olaño 17,395 Reputation points Independent Advisor
    2025-11-04T23:39:22.4033333+00:00

    Got that. It's the same with a know regression in the New Outlook for Mac (v16.102.3+), the symptoms matches. This has been reported since October 2025.

    By the way, have you tried to drag into the “Attach” bar at the top of the window, the small area next to the subject line still accepts drags.

    Also, if you rely heavily on drag-and-drop for attachments, quickest runaround would be to use OWA or Legacy outlook, until a hotfix is rolled out on future updates.

  2. Kimberly Olaño 17,395 Reputation points Independent Advisor
    2025-11-05T02:22:32.5133333+00:00

    Have you tested it on OWA?

    Log into the same account at https://outlook.office.com or your company’s webmail URL. If drag-and-drop there also fails, it’s a server-side policy, not a Mac client bug.

  3. Kimberly Olaño 17,395 Reputation points Independent Advisor
    2025-11-05T03:09:35.26+00:00

    Is your working Exchange account a Microsoft 365-hosted mailbox? And the other one is an on-premises or hybrid Exchange mailbox?

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