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
    2022-07-13T15:15:47+00:00

    I experience the same seemingly erratic behaviour. When I send the email through the Word-sharing option, it looks as if the file is attached, but it is mostly not sent, i.e., it seems to disappear just after I press "send".

    I cannot find any consistency; sometimes it works, mostly not.

    Outlook is linked to Gmail; and I use the "New Outlook" as well as the latest version. The OS is Big Sur with the latest updates.

    File size does not seem to matter as long as they are not too large to send.

    There are no add-ins (as far as I can tell).

    This only started recently, perhaps after the latest update, but I did not mark the exact date when this started, so I am not sure. There is no virus or malware programme, and no new apps were recently added.

    Mysterious?

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  2. Anonymous
    2022-07-14T09:27:50+00:00

    Hi there

    We have exactly the same problem.

    All Mac's on Monterey 12.4 all Outlook versions 16.63. We are using Google Workspace and all client computers randomly drop attachments.

    I have disabled (temporarily) Webroot Antivirus - No difference

    Attachments are a mixture of Excel files, PDF's and Word docs.

    All these points are exactly the same.

    • This does not happen every time—sometimes it doesn't happen for a week and sometimes it happens 5-6 times a day. On average I would say it happens at least 2 times a day.
    • Usually on the second email attempt to send my attachment, it goes through, but the odd time it will fail 2-3 times in a row
    • It does not happen for any one client in particular and there are no firewall issues on my end
    • It will happen for attachments between 30kbs and 15mbs so I gather it is not a size issue, especially when the attachment goes through the second or third time without issue.
    • Around 5 weeks ago, support told me an engineering team was going to look into this specifically, but I have not been able to receive any updates on this after asking.

    They always work the first time through webmail.

    There are over 20 affected users.

    Any ideas would be greatly received.

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  3. Anonymous
    2022-07-21T18:31:11+00:00

    See the following thread for this same issue (no fix listed there either): https://answers.microsoft.com/en-us/outlook_com/forum/all/outlook-for-mac-emails-randomly-drop-attachments/973edbdb-b5e6-45ad-8254-3d6e5ed5ae2a?page=1

    We have a person here at work with the same issue.

    MacBook Pro 16" 2021 M1 Pro

    Monterey 12.4

    Outlook for Mac 16.63

    It happens when sending email about 10-20% of the time.

    Gmail back-end seems also to be a common thread.

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  4. Anonymous
    2022-08-09T18:00:34+00:00

    Same problem by a month now. I also tried to delete the account, unistall the Outlook app and reboot the entire system.

    We cannot work like this so I do need to fix it.

    Please update.

    Tnx

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  5. Anonymous
    2022-08-12T03:38:05+00:00

    I'm having the exact same problem. Don't know something hasn't sent until I go into the sent file.

    I'm having to swap back to Gmail to reliably send emails with attachments, which is laborious.. Plus, I hate the Gmail interface.

    I've done updates, nothing seems to be working.

    I miss the legacy version. This one just doesn't seem as stable.. and now I can't send emails with attachments, in no pattern I can ascertain. Driving me nuts.

    Please fix this Microsoft.

    I'm on Version 16.63

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