This problem has been giving me some headaches for a while now.

I have two servers running in my office, one running Ubuntu Hardy Server Edition, which functions as my web server, as well as a Win2K3 machine that runs Exchange 2003, as well as several access databases.

I have a php based help desk tracking system on the webserver that uses a mail() function to send confirmation messages to registered supporters indicating that a change has been made to a ticket. the linux machine runs sendmail to manage mail transport.

Here is the problem: I need the linux machine to use the exchange server to send the messages. I have tried configuring sendmail to relay through the exchange server, but exchange drops the messages. Previously, this had worked, but the domain of the mail was incorrect. the messages should be coming through as helpdesk@domain.com, but instead were coming through as "Web Administrator webadmin@webserver" (verbatim, not edited).

How can I get sendmail to send messages properly? I have an account set up in exchange titled helpdesk@domain.com which I would like sendmail to use for ALL outgoing mail, regardless of the user that created it.

Is this feasible? I'm not particularly attached to sendmail. Actually, I hate it. My server runs webmin if that would make things easier.

Thank you for any help, and I can provide any information you need (so long as it doesn't compromise security)

Thndrchld

If I correctly understand what you mean, then call sendmail with -fhelpdesk\@domain.com and ensure that the apache user is in sendmail's trusted senders list.

I don't actually call sendmail. It's invoked by the php mail() function. My biggest problem that needs to be dealt with first, though, is why Exchange is dropping the relayed messages. I have the webserver (192.168.1.201) setup as an authorized relay agent on the exchange server(192.168.1.200).

when I invoke sendmail from the command line to test, it behaves as if the message has sent properly, but the message is never delivered to the recipient (exchange account).

And the logs say....

Well, that's my next question: Where does sendmail store its logs? I looked in /var/log, but there's nothing that seems specific to sendmail.

I also checked /etc/mail, but not there either.

I haven't looked at the Exchange log yet, I will when I get into the office this afternoon.

Well, never mind. I found it in syslogd. Here is what it says:

Dec 17 06:21:02 webserver sm-msp-queue[14354]: nBGNounK010826: to=(exchange user)@(domain).com, ctladdr=webadmin (1000/1001), delay=11:30:06, xdelay=00:00:00, mailer=relay, pri=3360049, relay=[127.0.0.1] [127.0.0.1], dsn=4.0.0, stat=Deferred: Connection refused by [127.0.0.1]

This is one entry. Obviously, I removed the domain and the user name. It looks to me like it's trying to relay through localhost. It should be relaying through 192.168.1.200. Why would it do that and how do I fix it?

http://en.wikipedia.org/wiki/Smart_host
http://www.google.co.uk/search?q=sendmail+smarthost

I've got smart host setup. I've tried it through the sendmail.cf, the sendmail.mc, and through webmin. It always tries to use 127.0.0.1 for the relay.

Have you set the smart host by IP address or hostname? If only hostname, try IP. Also, try sending test messages from sendmail manually.

Update: I've managed to get the Relaying to work properly. There was a DAEMON_OPTIONS directive that was routing messages to 127.0.0.1 I dnl commented it out and messages send properly now. However, they are not masquerading properly. I have specified a DM directive, but it appears to be ignoring it. I have also tried setting up a generics table to cause all outgoing messages from user webadmin to come from helpdesk@domain.com, but that is not working either.