Impossible to join a file to an email

Caroline Brunner 0 Reputation points
2023-07-18T08:20:27.4066667+00:00

Hello, We have a problem.

Sometimes (even often), when we send an email with attached file, the attached file is not sent to the receiver.

Could you say why? What is the resolution of problem?

We work on Mac computer.

Thanks

Caroline

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Olaf Helper 46,031 Reputation points
    2023-07-18T08:25:11.33+00:00

    With that less on iformation (like file type) it's difficult to guess somethin other then: Your antivirus-scanner removes the file, because they are in some way suspicous.


  2. Faery Fu-MSFT 19,096 Reputation points Microsoft Vendor
    2023-07-19T06:20:37.73+00:00

    Hi @Caroline Brunner ,

    Does this affect all users in your organization?

    Is the problem occurring with a specific recipient or random recipients?

    Sometimes (even often), when we send an email with attached file, the attached file is not sent to the receiver.

    Since the issue cannot be reproduced every time, it might be difficult and time consuming to troubleshoot and figured out the root cause. Below are some tips which might help to narrow down the issue for your reference.

    1. Do attachments appear correctly in the sender's sent items folder?
    2. Send mails with multiple attachments from OWA instead and see if all attachments can be received. If it never occurs in OWA, it's likely to be an issue with the client side.
    3. If the issue can be reproduced in OWA as well, you can consider configuring pipeline tracing on the Exchange server side to capture copies of email messages as they move through the transport pipeline and see if more clues can be found.

    Besides, you can also refer to some known issues about Outlook for Mac:

    Attachments missing from emails when using macOS Big Sur

    Outlook fails to send attachments and inline images when sending a signed or encrypted email using the new Outlook for Mac


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