Have a sister company I now support that has been using SBS03 for years with nothing but message/sender/connection filtering. They tell me they have always had problems with random emails not being received. Sender resends and they get it. So I pointed their primary MX to my Barracuda and had it then deliver their mail over our VPN link to their server. This gives me ability to see exactly what is received and delivered. So yesterday they show me an email re-sent to them that shows it was originally sent earlier and not received. I find the original email in my Barracuda and it shows successfully delivered to their server. Nothing is their junk email in outlook and no one received it. I have all our IP's, domain, etc white listed on their SBS server so nothing from us should be getting blocked. Even before when their primary MX was on their IP they would miss emails from us and we were white listed. Am I missing something else? I've never used the built in filtering in Exchange before and am not to familiar with it. The advanced settings on the SMTP Virtual Server properties shows that only connection filtering is being used. It's to the point where I'm going to stick my old Barracuda, before I went to the virtual appliance version, on their IP (which is now their secondary MX) and turn off all filtering on the server.
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