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: Most helpful
Most helpful Newest Oldest
  1. Anonymous
    2023-08-17T10:03:27+00:00

    Also experiencing the same error.

    I will test removing the Hubspot Add-in, however I'm not super happy that this seems to be the best solution as we are using Hubspot as our main CRM. We are sending 100+ emails per day and all of our Sales people are experiencing the same thing - not great if you are trying to send out info & contract material to clients.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  2. Anonymous
    2023-08-16T14:42:47+00:00

    I received an Outlook update and installed...but no luck. Still removes attachment.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  3. Anonymous
    2023-08-15T16:38:13+00:00

    I'm going to give this a shot!

    Thanks!

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  4. Anonymous
    2023-08-15T14:54:32+00:00

    I am yet another person with this problem. Started noticing it about 2 months back. Looks so unprofessional when emailing new clients terms and they just disappear etc. Sometimes needing to send it 3/4 times before it eventually attaches.

    My signature also doesn't pull through as well, just looks so amateur!

    I notice Microsoft says its only happening to a small number, well there is quite a few in this thread now.

    Notice some say remove hub-spot. We use this for our CRM system and out marketing/sales, so really dont want to have to do this.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  5. Anonymous
    2023-08-11T13:20:24+00:00

    I'm responding to this one so that other people can see it. I've been using this workaround since July 2 without fail.

    Click Outlook -> Work Offline -> Send your email with attachment normally -> Wait for it to show up in Outbox -> Click Go Online

    Thanks to Mike Edmonds1 who saved my sanity! This also fixes any signatures that are attached files.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments