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Occasionally I have received the following error when trying to send emails to other organisation from Exchange 2007:

Diagnostic information for administrators: Generating server: exchange-server.internal.domain.com enduser@externaldomain.com external.mail.server.domain.com #500 Firewall Error ##

It turns out that this is actually due to the Cisco router inspecting SMTP traffic. Entering the command below into IOS fixed the issue:

no ip inspect name SDM_LOW esmtp