exchange server outbound smtp to internet

mcast

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EDIT: got it working, wrong port was configured on the outbound virtual server, yes I'm an idiot.

I installed exchange 2003 at home yesterday, as I needed to refresh something for a client. I just wanted to simply send it an email from gmail and reply. The incoming email is fine but no matter what I can't get it to send, the mail just gets stuck in a queue with no ndr.

Many hours on google later I still can't find the answer.

I set it up very similar to this article like so and I remember it being that easy years ago. I just put an MX and A record for my routers wan IP on a domain name I own to test. Obviously it works as I'm getting the external mail.

I've tried pointing the outbound exchange virtual server to a tiscali DNS server listed on my router, also tried pointing it to smarthost smtp.tiscali.co.uk (tried both anon and auth). My router port 25 is open both ways for smtp and I can telnet to smtp.tiscali.co.uk using port 25. I'm on tiscali dynamic IP, I know the IP will change, but I only need to test for a couple of days.

If I do a nslookup on the router wan IP address specified in my MX record I get this:
Name: 2xx-1xx-xx-xx.dynamic.dsl.as9105.com (which is not my domain name obviously)

I just wonder if I'm not understanding the DNS correctly. Could the target mail server be doing a reverse lookup and not seeing the correct domain, thus rejecting the messages? If so why are they just sitting in my queue?

Any help would be appreciated.
 
Last edited:
I think you need to add an SMTP connector for * pointing at your smart host and set to use the SMTP virtual server. Been a while since I done this though :)
 
Eulogy said:
I think you need to add an SMTP connector for * pointing at your smart host and set to use the SMTP virtual server. Been a while since I done this though :)
Click to expand...

I tried making a SMTP connector for * to point to smarthost it didn't work, but this is just really an additional type of virtual server for outbound mail (unless I'm reading it wrong). I think the vanilla default virtual server that is created when you install exchange is all you need.

But thanks :)
 
Are you running any AV on that machine? some block outbound SMTP to protect against mass mailing worms. I've had this interfere with exchange before.
 
I can telnet, ping, tracert, nslookup the smtp.riscali.co.uk from the box so I don't think it's a connectivity issue.

No AV on the build, just windows 2003 and exchange 2003 out the box, no av, no firewall.

The strange thing is I set smtp logging to max and see nothing referring to smtp in the eventvwr app log, only thing there is me manually restarting the smtp service.

The queue has "gmail.com" listed with a bunch of test messages i replied to, stuck in "rety" mode with the error "the remote server did not respond to a connection attempt".

this is driving me nuts.
 
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