[TheOnlyGonzo]

Ok i have been looking into this for quite some time now, and still can not come to a solution. I have a configured a webserver using Ubuntu 8.04 Hardy using sendmail (8.14.2.2)for a form on the webiste.
The only purpose for sendmail is to email information that is entered into a form on the website to an internal email. My mail server is configured on another server.
Right now I can submit info on the website and have it sent to the email account I have specified, and the webserver sends a reply mail to the sender informing them that their email has been sent.
Now the problem is no matter where this email is sent from (internal or external to the LAN), it will get stuck in the queue to be sent to the mailbox for the specified email account. The system log shows that the sending of the info from the website form, has timed out during the sending. It also shows me the IP address it tries to send to, which is the public address for my mailserver.
To my knowledge, I have never been able to get to my mailservers public address. This is because my ASA5520 does not allow traffic from internal (private address) to get to a destination on the DMZ (public) address. I can only get to my mailserver thru the private address.
So my question is this: Is there a way in sendmail to configure it to send to a private address instead of the public address it is trying currently? If there is, then I should be able to get the info being sent from my website to the desired mailbox. If not, then does anyone have any suggestions as to another email service to use in Ubuntu other than sendmail?

[TheOnlyGonzo]

Anyone??

[briealeida]

If the two servers are on different LANs, you have to use the public address. Private addresses (like 192.168.0.0 or 10.100.0.0) are non-routable by definition. Is your mail server true DMZ?

Have you looked at the ASA configuration? I have a similar Cisco ASA and there are lots of configuration options.

[TheOnlyGonzo]

They are not on different LAN's. The private address for webserver is 192.168.0.201 and the mailserver is 192.168.0.9. What sendmail is trying to do is send to the public address of my mailserver which is on a true dmz.

What I have learned from Cisco, is that the firewall by default will not allow you to go from inside (private ip) to the outside (public address) and then try to come back in to the dmz. This is a security risk if you allow it. Cisco states that it is a potential for spoofed addresses to gain access inside. So the only way for me to get to my mailserver is by private IP, which is configured in the firewall to allow access from inside to dmz.(192.168.1.xxx has access to 192.168.0.9).
So my thinking would be to configure, if possible, sendmail to send to the private address instead of the public one.

Any ideas??