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Thanks for your reply. &nbsp;I've removed the static (inside,outside) entries with port definitions from the ASA per your recommendation and this appears to have fixed the problem. &nbsp;I'm going to keep testing and make sure then accept this as solution. &nbsp;Thanks.
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Thanks for your reply.  I've removed the static (inside,outside) entries with port definitions from the ASA per your recommendation and this appears to have fixed the problem.  I'm going to keep testing and make sure then accept this as solution.  Thanks.

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There is a post on here somewhere from me asking the same question like 4 years ago hehe ;)
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There is a post on here somewhere from me asking the same question like 4 years ago hehe ;)

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Thanks for your fast and accurate response.
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Thanks for your fast and accurate response.

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We have an Exchange Server that is reporting its IP address as that of the router as opposed to the correct outside IP address. &nbsp;Let's say its internal address is 10.0.0.50, and it's outside IP address is 209.157.220.241. NAT is being performed by a Cisco ASA, the ASA is connected to a Cisco 2800 series router who's IP address is, let's say 209.157.220.240. &nbsp;If I telnet somewhere from the Exchange Server's console, I'm being seen as coming from the routers IP address as opposed to the outside IP of the Exchange Server; this is causing some email to fail. &nbsp;<br />
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How can I make the Exchange Server be seen as though it is coming from the correct IP address? &nbsp;Not sure if this is a Cisco or Microsoft question but if I had to guess it is squarely in the hands of the ASA.<br />

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We have an Exchange Server that is reporting its IP address as that of the router as opposed to the correct outside IP address.  Let's say its internal address is 10.0.0.50, and it's outside IP address is 209.157.220.241. NAT is being performed by a Cisco ASA, the ASA is connected to a Cisco 2800 series router who's IP address is, let's say 209.157.220.240.  If I telnet somewhere from the Exchange Server's console, I'm being seen as coming from the routers IP address as opposed to the outside IP of the Exchange Server; this is causing some email to fail.  

How can I make the Exchange Server be seen as though it is coming from the correct IP address?  Not sure if this is a Cisco or Microsoft question but if I had to guess it is squarely in the hands of the ASA.


Wrong IP in message headers causing NDR's

Hardware-based firewalls provide more sophisticated protection for inbound and outbound traffic than the simple Windows software firewall or the basic NAT firewalls found in routers. These devices implement techniques such as stateful packet inspection, deep packet inspection, and content filtering; and may include built-in antivirus and anti-malware protection.

Hardware Firewalls

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.