Outlook for Mac – Calendar Attachments Greyed Out on MacBook Neo

DP 0 Reputation points
2026-09-09T07:23:22.7866667+00:00

Hi,

We are experiencing an issue with Microsoft Outlook for Mac where attachments in calendar events appear greyed out and cannot be opened or downloaded.

Issue Description

One of our users is experiencing this issue when her assistant creates calendar events on her behalf and adds attachments, such as PDF or Word files.

When the user opens these calendar events in Outlook on her MacBook Neo, the attachments appear greyed out and cannot be opened or downloaded.

However, the issue does not occur when the user creates the calendar event herself. In that scenario, she can open and download the attachments normally.

The user has two MacBooks. We performed similar troubleshooting on both devices. The issue has been resolved on her MacBook Pro (M4 Max) but continues to occur on her MacBook Neo.

MacBook Neo Device Information

  • macOS: Tahoe 26.6.2
  • Processor: Apple A18 Pro
  • Microsoft Outlook: Version 16.112.3 (26083020)

Troubleshooting Performed

  1. Update the Outlook to the latest version 
  2. Checked Outlook permissions
    • Confirmed that Microsoft Outlook has Full Disk Access.
    • Confirmed that Microsoft Outlook has the required Files & Folders access.
  3. Checked the default PDF reader
    • Confirmed that Preview is set as the default application for opening PDF files.
  4. Reset the Outlook account/cache using two methods
    • Reset the Microsoft 365 account via: Tools → Accounts → Select the affected Microsoft 365 account → Manage → Reset Account
    • Manually cleared the Outlook cache from: ~/Library/Containers/com.microsoft.Outlook/Data/Library/Caches/
  5. Signed out and signed back in
    • Signed out of her account in the Outlook application and signed back in.
  6. Tested with a calendar invitation
    • Sent a test calendar invitation to her other email account that signed in on the Outlook application
    • The calendar event appeared correctly on her MacBook Pro.
    • However, the same event did not appear on her MacBook Neo.

The issue continues to persist on the MacBook Neo despite completing the troubleshooting steps above.

Could you please advise on any additional troubleshooting steps we can perform or whether this is a known issue with Outlook for Mac or macOS Tahoe?

Please let us know if you require any additional logs or diagnostic information from the affected device.

Thank you for your assistance.

Outlook | MacOS | Legacy Outlook for Mac | For business
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  1. Hendrix 990 Reputation points Independent Advisor
    2026-09-09T17:30:56.1833333+00:00

    Hi DP,

    Thank you for your detailed information about the issue.

    Based on my research, there are currently no official articles or announcements from Microsoft regarding this issue. I also cannot find this exact delegate-calendar attachment behavior in Microsoft’s published Outlook for Mac known issues list via Fixes or workarounds for recent issues in Outlook for Mac | Microsoft Support. Therefore, this may not be a known issue but is more likely a device-specific Outlook profile, synchronization, or local macOS user-context problem.

    To narrow down the issue, please try signing into Outlook on the web using the affected user’s account, then open the same delegate-created event and test:

    • Does the event appear in Outlook on the web?
    • Is the attachment visible? Can it be downloaded?
    • Does a newly created test meeting appear immediately?

    If you can do this on the web, it means there is something wrong with your Outlook client. In this case, try creating a new profile on her MacBook Neo by following the steps in Manage profiles or identities in Outlook for Mac | Microsoft Support, then test again to see if it helps resolve the issue.

    Hope this information would be helpful. Should you have any further questions, please feel free to share them in the comment below. I'm very happy to help.

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