Microsoft Outlook not sending attached files

[nrnorman]

I am associated with a firm that utilizes Mac computers in conjunction with Microsoft Outlook for communication purposes. Presently, we have encountered an issue involving two employees who are experiencing difficulties while attempting to send email attachments. Specifically, after attaching a file and sending the email, there have been instances where the attached file does not successfully transmit. This anomaly appears to occur sporadically, defying easy identification of a consistent pattern.

If anyone within the community possesses insights, recommendations, or support relevant to this matter, your input would be immensely valued. We are eager to address and resolve this situation promptly. Your assistance is sincerely appreciated.

Thank you for your consideration.

Best regards, Nick

 

[SCP]

1. Have you analyzed the combined size of the attachments for each unsuccessful outbound email?
2. If you duplicate the unsuccessful email and try to resend, does it make it through or fail yet again?
3. When you say Outlook, what version and what mail server configuration? Are you referring to executable on the Mac, Office 365, version? Mail server from ISP, MSFT, freemail, hosting service, dedicated?
4. When you say "the attached file does not successfully transmit" does that mean that the email still makes it to recipient without the attachment(s)?

Quick guess is that the two employees are exceeding attached file size limit, but that's a shot in the dark in light of missing information.