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
    2023-05-26T15:36:46+00:00

    This issue has persisted for more than a year. Despite frequent cosmetic updates to the app, the underlying problem remains unaddressed.

    I previously posted about this here, only to receive a standard reply suggesting I contact the Outlook for Mac support team. This team seems to be instructed to lead customers on an unproductive chase with tasks that ultimately lead to no resolution.

    Below is the link to my post: https://answers.microsoft.com/threadauth/090302fb-4eb2-4696-90a0-330cc6d1bea7/messages/fcd2ed9c-a1be-40e1-a8a2-bb51d59507c

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  2. Anonymous
    2023-05-25T07:19:54+00:00

    I have suffered from this problem in the past too. However, these days I don't have the attachment problem anymore. Hopefully others experience the same.

    I am using a Mac Studio with Venture 13.0.1. And my Outlook version is 16.73.1.

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  3. Anonymous
    2023-01-04T19:09:17+00:00

    Just a heads up, I've updated to the latest version available 16.69 (22123000) and attachments with digital signatures appears to be fixed. This is the first time I've been able to do both successfully.

    EDIT: Although I discovered another bug where I couldn't actually delete the email afterwards lol. "Delete" was greyed out, even after restarting Outlook.

    Image

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  4. Anonymous
    2022-12-13T17:16:22+00:00

    Hi, i had the same issue that's when I started googling and found this website.

    what worked for me, I used the "newer version" of outlook. And changed it back to "old version" in the options for outlook, then everything worked. later changed it back and no more issue's

    hope that helps..

    greetings

    This didn't work for me.

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  5. Anonymous
    2022-12-13T15:15:04+00:00

    What the latest on this issue? Has Microsoft eliminated the problem?

    Does combination of latest Outlook (16.67) with latest Mac (13.0.1; Ventura) work well now?

    I can confirm that for Microsoft Outlook 365 version 16.68 (22121100) - installed today, on MacOS Ventura 13.0.1 - it's still not working for me.

    Attachments that are added to signed emails get lost, with only an smime.p7m attachment appearing on the recipient end. Emails without attachments arrive correctly on the other end (showing as signed).

    I don't understand how some people aren't experiencing this, and why Microsoft thinks the issue is closed?

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