Intermittent Issue with Missing Email Attachments in Exchange Server 2019

Celso Javier Guzmán Díaz 0 Reputation points
2025-01-21T18:53:14.28+00:00

Hello Community,

 

This is an issue I hadn’t experienced before. For example, today I sent an external email of 9 MB with 3 attachments, but the recipient, who is on my Exchange Server 2019 (up-to-date), only received 2 attachments. When I resent the email, they were able to receive it without any problems.

 

This is also happening with other users in my organization, and they have reported it to me. I’ve checked and found no restrictions, and it’s not related to message size either. I tried replicating the issue, but it no longer occurs. This is concerning because the user who reported the issue today is a VIP.

 

I had an Endpoint AntiSpam enabled, which I have already deactivated, and I also have a WatchGuard firewall. I need to determine if the problem is related to this, as an initial review indicated that everything was fine.

 

Has anyone else experienced this issue?

Exchange Server
Exchange Server
A family of Microsoft client/server messaging and collaboration software.
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  1. Andy David - MVP 151.6K Reputation points MVP
    2025-01-21T18:56:28.0433333+00:00

    Im leaning towards AV when I hear this. When was the anti spam disabled?


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