Ok, another strange problem.
I am moving all of the mailboxes from a SBS 2003 to a SBS 2008 machine. I disabled (deleted) the SBS 2003 Outbound connector and tried to send emails through the SBS 2008 machine (oh, btw, this is all in the Microsoft Paper that tells people how to migrate from SBS 2003 to SBS 2008, this is one of the first steps in the migration). Now, here is where things start going wrong. Outbound emails are stuck in queue.. did a little troubleshooting and it appears that only the OLD SBS 2003 can even connect to any servers outside of my network. Here is how I figured that out.
I ran the cmd prompt on the 2008 machine and typed in: telnet smtp.1and1.com 25 Could not connect
I ran the same command from the 2003 machine and it connects
I ran the same command from ANY other PC in the network and they cannot connect.
I ran the same command from a Laptop that only connects to the Internet... it does not connect to the AD domain, so it is not getting any policies pushed to it... and as long as I am connecting to their network I CANNOT connect to the server using the telnet command.
If I disconnect my laptop from their network and put in my Verizon card, I can telnet all day long to that SMTP server.
So, I figure the problem is the Firewall.
Soooo digging into the firewall (it is a Calyptix AE500) I cannot figure out where to allow the other machines to connect via port 25 over smtp. I know it has to do something with the settings in there and its probably one of the best features in that if a PC from behind the firewall goes nuts and starts blasting out emails, this firewall will stop all that nonsense.
But does anyone know where I can make the change to ALLOW outbound traffic to connect to a SMTP server besides the one thats using it now?