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
    2022-09-12T20:50:21+00:00

    Hello Thiru,

    I clicked on the Reply button when this thread was started by Nathan, so I thought I was replying to him but I might be wrong. I apologise and didn't mean to call you by the wrong name.

    We have a few reports of this issue but the issue is not reproducible on demand by the customers who reported this issue and we cannot duplicate this issue in-house.

    Please reach out to support as we are looking for specific information that we can relate to our telemetry logs and investigate this further.

    Thanks & Regards,

    Pawan Kapoor

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  2. Anonymous
    2022-09-13T19:22:55+00:00

    Pawan,

    This issue is most definitely reproducible. I have already reached out to support and have an open ticket, Case #:32889264. The recommendation was to revert to the old Outlook. That is not a good option as I am having other issues with "old Outlook", which is what led me to flip the switch to the New Outlook to begin with... Now I am stuck with significant issues on both versions! I am happy to demonstrate this particular problem to someone from escalated support - please have someone contact me. This is a major problem and needs to be remediated ASAP.

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  3. Anonymous
    2022-09-14T00:16:00+00:00

    This issue just started for me on September 12, 2022.

    Mac OS Monterey 12.4

    MacBook Pro 2021, Apple M1 Max

    Outlook 16.65

    Office 365 higher education account

    Has happened with various file types including PDF, XLS, DOC, JPG.

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  4. Anonymous
    2022-09-14T00:26:41+00:00

    Hello Nathan,

    Can you please open a support ticket, you can do this from the Outlook Help Menu > Contact Support. We want to collect specific information about this issue to help investigate.

    Thanks,

    Pawan

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  5. Anonymous
    2022-09-14T12:46:13+00:00

    Same issue but I made an interesting investigation. In general I add a S/MIME signature to my E-Mails. When I do not attache my S/MIME signature attachments were sent. I tried it several times now. With S/MIME attached other attachments getting lost. Without S/MIME attachments will be sent.

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    6 people found this answer helpful.
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