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
    2023-07-03T02:48:52+00:00

    Thanks, I've Contacted Support. They've confirmed that it is a bug that they are going to patch but couldn't give a timeline for that.

    Having said that, the simplest work around they had was: "Click 'Outlook -> Work Offline. Once done try sending a test email with an attachment to yourself. Once the email is stuck in Outbox, set Outlook to online mode and see if the email is sent with the attachment."

    This worked and seems to also work for sending emails to people other than myself.

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  2. Anonymous
    2022-09-15T05:55:08+00:00

    I raised a support ticket and got a reply today. At least the issue is now on the bug list.

    Outlook fails to send attachments and inline images when sending a signed or encrypted email using the new Outlook for Mac

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  3. 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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  4. Anonymous
    2022-08-15T20:18:17+00:00

    This is my concern as well, Adsha. We take great care to make sure all of our correspondence is professional and clean but not having attachments go through, after we've tried every method of attaching them, reflects horribly on our professionalism. C'mon Microsoft.

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  5. Anonymous
    2022-08-12T18:03:14+00:00

    Monica,

    To revert to the "Legacy" version, launch Outlook, click Help > Revert to Legacy Outlook. You'll be greeted with the previous version of Outlook and will need to sign back in to your email accounts as it seems to use a different back-end than New Outlook does. I see many people have reported that this works and I am instructing the 2 people in my office with the issue to do the same.

    See below as Microsoft has acknowledged the issue and has no fix as of yet, so this would be the best option until they fix it.

    Best of luck!

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