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
    2022-08-25T13:13:48+00:00

    Even worse, Microsoft seem to be starting to force the roll out of the new version. A couple of days ago Outlook announced that the new version would start automatically when the app was next closed. Fortunately after it did so there was still the option to then roll back to the Legacy version. My concern is that at some point they will force the 'update' and remove the legacy option - at that point I will be switching back to Apple Mail if they haven't sorted the problem.

    TBH the only reason I don't use Apple mail is that we have issues with PDFs that are attached to emails with Google Mail...

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  2. Anonymous
    2022-08-25T15:25:37+00:00

    I am having the very same issue (MacOS 12.5.1 and Outlook version 16.64). Please help! It's been happening for a while. I am an author, and I sent a manuscript this morning to a very prominent potential endorsement of an upcoming book, and it was embarrassing to have to re-send the email again because my attachment did not send.

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  3. Anonymous
    2022-08-26T06:34:35+00:00

    Same problem here with Mac Studio installed with with Monterey 12.4 and Outlook 16.62. Worrying thing is that it doesn't happen all the time but in totally unpredictable ways! And it causes multiple of my customers to think that I am no good at my job! It is also clear that it doesn't only occur with the most recent version of the office suite because I was forced to re-install an older version (16.62) because the most recent PowerPoint version also contained a very irritating bug. This whole problem has costed me lots of time! Very embarrasing for a company that prides itself on providing productivity for the user.

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  5. Anonymous
    2022-09-02T14:58:57+00:00

    Same issue here. 2021 MacBook Pro, Monterey v12.5.1, Outlook for Mac 16.4

    I believe I updated to the newest Monterey sometime during this problem, which has been going on for about 6 weeks now (mid-July?).

    I was starting to think I was getting really absent-minded because of the number of clients that would email back and say "no attachment, can you re-send?" The problem is periodic and seems to have no rhyme or reason, although it is increasingly frequent these days.. I can re-send the same email with the attachment re-attached and it might go through one time and might not another time. I can start a new email and attach the item and it may or may not go through. (As the OP mentioned, the original email shows up as sent, but without the attachment even though I triple-checked to make sure it was there before I hit send.) The type of document and whether I drag/drop the attachment or use the "attach" tool to select the document doesn't seem to make any difference. The suggested diagnostic step of going into safe mode and trying to send an email with an attachment would be great IF none of my attachments ever went through, but some do and some don't. I'd have to send 100 over the course of a day to see if all 100 went through or not.

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