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
    2023-07-17T09:58:13+00:00

    The same problem here as well. It started about 6 weeks ago and happens several times a day. Currently, it is rather a matter of luck when you get an eMail with the attachments going out. This is MAXIMUM frustrating!

    By the way, not only the pure attachments are deleted, but also all inserted images (e.g. from the signature). Before the sending process the mail is still correct in Outlook, as soon as it is in "Sent" the attachments are missing. Sometimes it works with the first resend, sometimes it takes 2-3 tries.

    Setup here:

    • Microsoft Outlook for Mac (Version 16.75, 23070901)
    • License Microsoft 365 subscription
    • MacBook Pro
    • Apple M1
    • macOS Ventura, Version 13.4.1 (c)
    • German language

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  2. Anonymous
    2023-07-17T04:30:15+00:00

    We're having the same issue at our small all-Mac business.

    1. Drag and drop attachment.
    2. Attachment shows in the message.
    3. Recipient doesn't receive the attachment or images.
    4. Message in "sent items" doesn't show attachments or images.

    This showed for one team member about 3 weeks ago and has just started happening to me.

    It's a very frustrating silent bug that initially had me thinking I was losing my mind - and it makes it very difficult to do business.

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  3. Anonymous
    2023-07-14T13:13:03+00:00

    I have the same issue but I noticed that also images are not being sent. And I also discovered that I only have the issue when a mailinggroup is the receiver (TO or CC). So when I am sending to a mailinggroup with several email addresses, I have the issue.

    Mac office version: 16.76

    Mac OS 13.4.1

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  4. Anonymous
    2023-07-14T12:50:39+00:00

    Hello,

    A customer of mine is suffering from this bug.

    I have found 2 work arounds, either:

    Revert to legacy outlook and sending from that outlook works with attachments, just like what Microsoft have said.

    -Go to menu bar, click on Help. Select 'Revert back to Legacy Outlook' to switch to legacy Outlook.

    Or use outlook webmail, that also works.

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  5. Anonymous
    2023-07-14T12:39:53+00:00

    Hi, I just started having this issue about 3 weeks ago. Same as described. Any updates on fixes?

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