Exchange 2003 outbound email issue

September 24, 2008 · Filed Under Exchange 2003, Microsoft · Comment 

Yesterday it was a good happy day off for me until I received a call from my helpdesk that exchange outbound email is not working. Well it is known issue to my team since our last troubleshooting session with Microsoft consultant. However this post could help for exchange admins out there troubleshooting the same issue.

Let us now discuss the issue, its workaround, & the permanent solution.

Issue

Outbound email does not work with the following conditions true

  • You cannot send emails outside the organization.
  • You have an exchange frontend backend scenario.
  • You are using PPTP connection between the frontend and the backend exchange server.
  • You cannot ping your domain controller from the exchange frontend server.
  • ‘Message with unreachable destination queue’ keeps increasing.

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