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
    2023-08-14T15:45:02+00:00

    For the last 2+ months this issue has been driving me crazy and it's definitely unacceptable that Microsoft has yet to provide a fix for such an important issue.

    Over the timeframe I have been encountering this issue, I've been stalking this message board and appreciate everyone's input and workarounds. Like many others, I have been composing my emails with attachments in the app, saving in drafts, and then eventually sending from the web version. I've tried installing both beta and regular updates, but nothing ever seems to be consistent.

    With that being said, one of the more recent previous posts mentioned the possibility that Add-Ins could be causing the issue -- Particularly the HubSpot integration. Over the past few days, I have removed the HubSpot Add-In from my Outlook desktop app and this has worked like a charm. Since removing this and restarting the app, I have not had any problems successfully sending emails with attachments from the desktop app.

    As a result, for those of you that have the HubSpot Add-In installed on your desktop app, I would recommend giving this a try to see if it works for you!

    ...knowing that we have all been through with this issue, it also wouldn't surprise me if I suddenly start having problems again :)

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  2. 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.

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  3. Anonymous
    2023-08-15T16:38:13+00:00

    I'm going to give this a shot!

    Thanks!

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  4. Anonymous
    2023-08-16T08:45:09+00:00

    Just did this - removed Hubspot add-in and sent a couple of test emails. All good so far... :)

    J

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  5. Anonymous
    2023-08-16T10:32:49+00:00

    Hi, as promised for today, is there any update?

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