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

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments

240 answers

Sort by: Newest
Most helpful Newest Oldest
  1. Anonymous
    2023-07-04T15:37:37+00:00

    Turning off "Undo Send" probably helped by chance as all other solutions (e.q. reinstalling Outlook, deleting account and re-adding). This bug was introduced about a week ago with last update. So hopefully the next update will fix it. It is indeed frustrating.

    P.S. I have another Mac on which I did not update Outlook to the newest version yet and guess what, no problem on this one.

    Was this answer helpful?

    0 comments
  2. Anonymous
    2023-07-04T12:00:23+00:00

    Initial test for me fixed it by turning off "Undo Send" in "Composing".

    Was this answer helpful?

    0 comments
  3. Anonymous
    2023-07-04T09:01:14+00:00

    I've started having exactly the same problem! It's so frustrating and makes me look really unprofessional. I'm going to stop using the Outlook app and start using Outlook online to send my emails and attachments - not ideal but I'm not sure what else to do!

    Was this answer helpful?

    0 comments
  4. 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.

    Was this answer helpful?

    6 people found this answer helpful.
    0 comments
  5. Deleted

    This answer has been deleted due to a violation of our Code of Conduct. The answer was manually reported or identified through automated detection before action was taken. Please refer to our Code of Conduct for more information.

    Comments have been turned off. Learn more