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
    2023-07-24T21:33:18+00:00

    Actually, this has been happening for over a year now. This thread was started I think in May of last year. I just think it's effecting more and more people as new updates roll out. So frustrating because there is no fix for this yet.

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  2. Anonymous
    2023-07-24T04:05:29+00:00

    Our organisation has been experiencing this issue for the last calendar month now, one by one a new colleague will experience this issue and the only way we've worked out how to fix it is to revert them to legacy Outlook (we're a fully Mac tech-house). We use HTML email signatures and it looks extremely unprofessional when another staff member falls victim to this bug after emailing numerous external clients and only realising a day or two later that their signatures have broken or attachments haven't sent. How can Microsoft have allowed this bug to escape into the wild and not fix it after over 1 calendar month is completely beyond me, especially when they're charging a monthly subscription for their Office 365 package, I expect better. Emails have had HTML signatures and attachments for over 20 years, how can they have managed to break such simple functionality on such a widespread scale and still not have fixed it?

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  3. Anonymous
    2023-07-21T23:54:17+00:00

    This is an issue as well as the fact that in-line images are not being sent. No error message is shown and the only way to know that images and attachments were not sent is to go to the Sent folder and click on the message there. Only the placeholder image boxes exist and not the images themselves.

    Using Outlook for Mac OS 16.75 / 23070901 (not beta)

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  4. Anonymous
    2023-07-18T08:48:40+00:00

    Switching to legacy Outlook solves the problem, or switching to Beta (I am a Mac user) can help. You can switch to Beta by using the steps here - Help menu > Check for updates > Advanced > Change the channel option to Beta > Check and get the available updates. However, you must ensure you have installed Office from Microsoft, not App Store. You can download Office from your portal.

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  5. Anonymous
    2023-07-18T08:47:50+00:00

    Switching to legacy Outlook solves the problem, or switching to Beta (I am a Mac user) can help. You can switch to Beta by using the steps here - Help menu > Check for updates > Advanced > Change the channel option to Beta > Check and get the available updates. However, you must ensure you have installed Office from Microsoft, not App Store. You can download Office from your portal here.

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