Trying to get SBS 2003 Default SMTP Virtual Server to use smart host in stead of "Direct Delivery"
Posted on 2009-04-02
I'm trying to get our 2003 SBS server to email out using what I understand the server calls a "Smart Host" which is just either: 1) our domain host's smtp server or 2) our ISP's smtp server. This sounds like it should be simple. I've followed instructions I've found here but it still seems to be sending out email directly to the recipient's email server (What MS calls "Direct Delivery" I believe). The reason for this is we have two web apps that need to email out. One is Trend Micro SMB antivirus. (notification reports) and the other is an order entry type web app built around .net.
The emails seem to go out from the web application. In the event log, I see many event 4000 and 4006 which basically say it can't make an smtp connection to the recipient's mail server.
What I've done:
In Server Management -> Advanced Management -> Internet Information Services -> "MYSERVER" (local computer) -> Default SMTP Virtual Server -> (right click - Properties). Delivery Tab -> Advanced -> Smart host: mail.optonline.net (I've also tried smtp.1and1.com, our email/domain host).
I've tried changing "Masquerade domain" to "ourdomain.com" which we have hosted with 1and1.com.
For the "Fully qualified domain name" , I've looked up my cable modem's host name (something like: ool-123abc.static.optonline.net) so that the "Check DNS" button works - reverse DNS checks out, I guess.
In "Outbound Connections" button, port 25 for "TCP Port" is unchanged.
For "Outbound Security" I checked "Basic Authentication" and put in the username and password that corresponds to the smtp server I used for the "Smart host". (I've tested those usernames and passwords directly with the service provider's webmail interface).
None of these changes seem to alter the default behavior of the outgoing SMTP server.
One other fact:Exchange server is not set up. As I understand it, Exchange and its smtp engine are separate from this IIS "Default SMTP Virtual Server"