Outlook 365 for Mac - not sending attachments

Anonymous
2022-05-27T14:24:12+00:00

I have an issue whereby Outlook for Mac is losing attachments when sending emails (typically, but not exclusively, PDF files).

If a file(s) is/are dragged and dropped into an email it is shown as attached and appears to send as normal. There are no error messages or bouncebacks, and the first we know that the email has lost the attachment is when we are advised by the recipient. Then when checking the sent folder, the email is there but again without the attachments.

Doesn't do this every-time though... sometimes the email goes with the attachments as it normally should.

I'm using version 16.62 (22052500)

Has anybody else had this issue and is there a fix? Or is it a software glitch?

Outlook | MacOS | Legacy Outlook for Mac | For home

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  1. Anonymous
    2023-09-22T08:29:15+00:00

    I've given up on direct updates from Microsoft, and now use this as the best source of information (credit to the other person who posted this earlier in the thread): https://support.nhs.net/2023/07/microsoft-365-alert-service-degradation-exchange-online-users-email-with-attachments-sent-from-outlook-for-mac-and-the-outlook-mobile-app-may-be-delivered-without-attachments/

    Latest updated from yesterday 21st September: Microsoft deployed a fix to update attachment logic that they have confirmed will reduce instances of this issue from occurring when users frequently add and remove attachments by 40 percent. Their development of a long-term solution to this problem is contingent on the telemetry they are collecting subsequent to the delivery of their attachment logic update, and Microsoft will provide a better estimation on the development of the long-term fix when available.

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  2. Anonymous
    2022-09-14T14:47:05+00:00

    Andreas,

    Yes, you are 100% correct.
    This issue ties to "New Outlook" and digitally signed emails.

    If the outbound emails are not digitally signed, the attachments deliver successfully.

    This issue makes the "New Outlook" simply useless - and probably not only in the professional environment.

    Can you please fix this issue asap.

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  3. Anonymous
    2022-09-03T14:54:29+00:00

    Sounds like your observations are exactly the same as mine! I deleted the Outlook version for Mac 16.64 from my applications folder and replaced it with version 16.62. Since that time the problem has disappeared!

    I will not update any of my Office 365 applications fro Mac until I have had explicit confirmation from Microsoft that they have removed all bugs from such new Office suite version.

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  4. Anonymous
    2022-08-25T15:25:37+00:00

    I am having the very same issue (MacOS 12.5.1 and Outlook version 16.64). Please help! It's been happening for a while. I am an author, and I sent a manuscript this morning to a very prominent potential endorsement of an upcoming book, and it was embarrassing to have to re-send the email again because my attachment did not send.

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  5. Anonymous
    2022-08-12T14:35:40+00:00

    Thanks I thought I was going crazy! How do I go back to a previous version of Outlook?

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