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
    2023-08-17T10:03:27+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.

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  2. Anonymous
    2023-08-17T11:12:43+00:00

    That's right. And it is extremely unprofessional. Nevertheless, we have now taken out the Hub Sales app. For colleagues of mine it seems to work again now. Unfortunately not for myself, although our admin has removed the app from the selection, it is still in my Outlook and causes problems. Somehow I can't delete it manually. Maybe someone here has a tip.

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  3. Anonymous
    2023-08-17T12:37:59+00:00

    Thank you.

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  4. Anonymous
    2023-08-17T16:12:03+00:00

    This recent update seems to have had no positive impact. Regrettably, we find ourselves back at square one with the initial problems remaining unresolved. Throughout the morning, I've experienced repeated issues with my emails, specifically with missing attachments. A tech giant like Microsoft must ensure that such foundational functions operate seamlessly. Immediate attention to this matter would be highly appreciated, but do not hold your breath, because these guys MOVE SLOW and I've lost confidence in their ability to find a solution.

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  5. Anonymous
    2023-08-17T19:46:06+00:00

    Removing the Hubspot add in from my Microsoft Outlook for Mac Version 16.75.1. has so far today fixed the issue.

    Again one day only, but a huge improvement since my attachments would only make it in my emails 50% of the times.

    Thank you for the suggestions in this chat.

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