Outlook for macOS: Dropping attachments (randomly)

Anonymous
2023-06-05T09:33:54+00:00

Hello all,

For some reason, Outlook for Mac is dropping attachments and images in the emails I send. It's random, but it happens to me quite often. I managed to find out that this issue has historically occurred with other people using older versions. It seems that this bug has returned to Outlook for Mac.

I have the latest version 16.75.

macOS is also updated, i.e., macOS Ventura 13.4 (22F66).

I didn't have this problem before. It appeared about a month ago. In the meantime, a new version of macOS has been released and there have been several updates for Outlook, but the situation persists.

Attachment randomly disappears from the e-mail which I send with the attachments and pictures. It looks very unprofessional.

This is example how it looks when I add picture to the e-mail when the message is sent.

If I try it once again on the second attempt the attachments/pictures are sent without issues.

I need help, please.Any advice?

Outlook | MacOS | Legacy Outlook for Mac | For home

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  1. Anonymous
    2023-08-30T22:08:07+00:00

    I'm using a 2022 13 inch MacBook Air running Apple M2 and MacOS Ventura 13.5.1. What I experience is that if you revert to Legacy Outlook, run it for a couple of hours and then revert back to New Outlook, everything works fine for a couple of hours. Then, it starts randomly removing attachments and pictures until it removes them all. As mentioned in this feed, it seems to be something with a permissions issue for cache pictures. If you have your Sent folder open, you can literally see it happen. You can send an email with a picture in it, it shows up with the picture in your Sent folder right away, then, it takes about 5 to 10 seconds and the email remains, but the picture goes away (changes to the broken link). Same with an attachment. And, I've tried using delay send for the new Undo feature or schedule send, same thing. What seems to be going on is Outlook is capturing the picture and attachment in a cache folder (as it does on the PC side) and then when it goes to pass it off to the Send mechanism, access to where it stored the picture/attachment is blocked and the sending and thus saving the sent email turns into broken.

    What I'm using now is the New Outlook on Windows 11 using Parallels. Guess what, Windows 11 on Parallels works every time, NO issues!

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  2. Anonymous
    2023-08-30T23:08:46+00:00

    Using a Macbook Pro with M1Pro chip; Using Ventura 13.5.1 with Outlook version 16.76.1

    For what it's worth, Legacy Mode in Outlook seems to bypass this problem--New Outlook mode is still an issue.

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  3. Anonymous
    2023-09-01T00:22:28+00:00

    What is going on at Microsoft!!!

    Now this Findtime bug for three days and no response!!

    Our users are seeing errors in Findtime "Your poll can't be displayed - Microsoft Community

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  4. Anonymous
    2023-09-04T09:51:52+00:00

    It looks like i was able to fix this problem by

    • updating to 16.76 (this alone didn't fix the issue)
    • then switching to legacy version of outlook
    • forwarding a couple of emails with attachments to myself to confirm that the legacy version works
    • switching back to new version of outlook.

    It's weird but it seems the issue which removed attachmends when sending or forwarding mails is gone now.

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  5. Anonymous
    2023-09-04T10:59:14+00:00

    i tried the same, but switching to legacy outlook makes me lose all email account i have, meaning it is completely empty.

    So i switched back to new outlook immediately.

    But i think what also works is not sending emails with attachment immediately but wait for a minute.

    Because sometimes you can see an attachment vanishing for a second inside the email and then reappearing.

    My interpretation was, that an upload happens in the background and if it does not succeed before sending the email, the attachment will be lost on the way.

    Did anyone else try some like that?

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