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

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments

240 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. Anonymous
    2022-06-29T17:14:51+00:00

    I am having the same issues, cant send PDF attachments, does any have a solution?

    Was this answer helpful?

    8 people found this answer helpful.
    0 comments
  2. NoOneCan 7,805 Reputation points Volunteer Moderator
    2022-05-27T14:34:27+00:00

    Are you using Outlook for Mac for Beta Channel builds version 16.62 (22052500)?

    If you are using the New Outlook for Mac desktop client, you can switch back to Legacy Outlook (Help menu and select Revert to Legacy Outlook) to check this issue.

    Was this answer helpful?

    8 people found this answer helpful.
    0 comments
  3. NoOneCan 7,805 Reputation points Volunteer Moderator
    2023-08-04T14:20:52+00:00

    There is a recent incident EX637339.

    Title: Some users' email with attachments sent from Outlook for Mac may be delivered without attachments

    User impact: Users' email with attachments sent from Outlook for Mac may be delivered without attachments.

    More info: Users can verify if they’ve encountered this problem in Outlook for Mac by reviewing their Sent Items to validate if a sent message contains an attachment. If users don't see the attachment, they can reply to the message in their Sent Items folder to reattach and send the message again. Current status: We're continuing to develop an Outlook for Mac update that will correct this issue, that we still expect it will be available for download in mid-August. We anticipate providing a release date by our next communication update.

    Scope of impact: This issue is specific to a very small percentage of users' email with attachments sent from Outlook for Mac.

    Start time: Tuesday, July 11, 2023 at 4:08 AM GMT+8

    Root cause: A conflict occurring with how our service detects attachment IDs before sending email in Outlook for Mac is resulting in the service removing attachments on sending email.

    Next update by: Wednesday, August 16, 2023 at 2:30 AM GMT+

    Was this answer helpful?

    7 people found this answer helpful.
    0 comments
  4. 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?

    Was this answer helpful?

    7 people found this answer helpful.
    0 comments
  5. 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.

    Was this answer helpful?

    6 people found this answer helpful.
    0 comments