Exchange SBS 2003 SmallBusiness Connector - not sending smtp to outside

Gregg Battaglia
Gregg Battaglia used Ask the Experts™
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I have a client using a Windows SBS 2003 server. All out going emails are stuck in the "SmallBusiness SMTP Connector" in the queue. The POP connector is working and between internal users is working. But you can not send any mail to the outside.

I reran the utility to setup the email service with no luck. I checked the DNS and was able to resolve the names of the addresses mail was being sent to. I am not sure where the problem could be. When I tried to set it up using a smarthost with godaddy it stayed in the queue and said "the remote server did not respond to a connection attempt"... I am able to ping the servers and resolve the names.

any idea where the problem could be? Thanks in advance for any help!
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Commented:
Hello!
First, I think, you should exclude connectivity problems, like firewalls, wich can drop your outgoing connection. Try, for example, type in  command promt "telnet mx1.hotmail.com". If it is answer with

"220 col0-mc4-f22.Col0.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Fri, 29 Jan 2010 4:44:39 -0800", then problem is somewhere else...

Author

Commented:
just typing that returns "could not open connection to the host, on port 23: connection failed" and I get the same thing when I do it on port 25.

I can ping it and its name resolves. The SMTP  relay should not be block since I can use outlook to send and receive mail to godaddys server using pop and smtp.

any ideas?

Commented:
type in  command promt "telnet  mx1.hotmail.com 25".
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Commented:
If you are forwarding mail to a smart host in the SBS Connector, they may have changed hosts or policies - for example , you may now need a username and password. This is entered into the outbound security dialog on the connector's property page.
If you are not using a smart host, your ISP may be blocking port 25. The previous comment will uncover that. In this case you MUST use the ISPs SMPT server as a smart host.  View their instruction for configurign a pop client and pay attention to the information for the SMTP host. Configure the connector just as you would a POP client.
In either case, you'll see e-mail filling up the queue. As soon as you fix the issue, mail will begin to flow.

Commented:
O, of course, "telnet  mx1.hotmail.com 25", sorry :)

Author

Commented:
as I said above I get the same message on port 25 as well. The odd thing is that if you use outlook you can send smtp mail when you do a send/rec ... so I would think that port 25 is not block from the ISP.

Commented:
try telnet  mx1.hotmail.com 25>>c:\telnettest.txt  from a workstation and post the response.

Author

Commented:
when I run the command you put it creates the file but it is empty. When I just run the command "telnet mx1.hotmail.com 25" it says:

"Connecting To mx1.hotmail.com..." for a while then it comes back with:

"Could not open connection to the host, on port 25: Connection failed"

This is on a windows 7 workstation not on the server. What could stop this connection? I dont have any restrictions on the router. Is there something in SBS that could block this? When I have a workstation setup to use a pop/smtp setup with outlook it does work so I have to assume that it is not blocked by Verizon. the SBS is not used as a fire wall and the firewall on the server is disabled. Not sure where the problem could be.
Commented:
Contact your ISP and ask if they are blocking port 25 and get the hostname of their SMTP Relay. If you need them, get theusername and password to utilize the SMPT server.
 
Waht are the settings in the POP Client for SMTP - outbound connections? If you can send mail then these exact settings can be used in the SBS Connector.

Author

Commented:
you were right... as it turns out Verizon is blocking port 25 for SMTP... You need to use their outgoing server which is outgoing.verizon.net and use your user name and password for your dsl account. Just another reason not to use Verizon. people think they are saving money but only wasting more in time dealing with them. Their people kept telling me that it wasn't blocked but it is. So there was the problem.

thanks for your help.

Commented:
Virtually all ISPs are regulating SMTP outbound to prevent SPAMMING.

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