Telnet port 25 to an SBS 2003 from Vista or Server 2008 fails.

I am attempting to troubleshoot an email problem. Our company is trying to send to another company and the email will stay in the Exchange queue and we will receive a delivery delayed notification from our exchange server.

- We have a Exchange 2007.
- The destination email is Exchange 2003 Sp2, with a firebox as their router.
- I have tested email to their location from yahoo and other domains - these were successful.

I was following instructions on testing telnet to port 25 and have determined that I can telnet to port 25 on the destination from an XP or 2003 server, but I cannot telnet to port 25 from a Vista or 2008 Server.

Any insight as to why the telnet in these cases fail?
Any thoughts on why we may be receiving the delivery notification delayed?

Thanks much!!!
mmack12Asked:
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Rajith EnchiparambilOffice 365 & Exchange ArchitectCommented:
Are you blacklisted? Or they may have greylisting enabled?
0
mmack12Author Commented:
We are not blacklisted. Additionally, we are able to telnet to port 25 from an XP machine & a Server 2003 machine on the same network.
0
mmack12Author Commented:
I am now seeing the following error in the firebox logs:

SM: policy="svc:24" src_ip="x.x.x.x" dst_ip="x.x.x.x" pr="tcp" src_port="24259" dst_port="25" src_intf="2" dst_intf="12" rc="590" msg="Connect timeout" proxy_act="svc:24"
0
mmack12Author Commented:
OK, so it turned out to be the Firebox was causing the issue. It had an SMTP proxy turned on. Once I removed that policy and waited about 2 minutes I am now able to email and Telnet port 25.

These 2 links had similiar problems.

http://www.experts-exchange.com/Security/Software_Firewalls/Enterprise_Firewalls/Watchguard_Firewall/Q_23863159.html

http://www.experts-exchange.com/Security/Software_Firewalls/Enterprise_Firewalls/Watchguard_Firewall/Q_24175884.html
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Email Software

From novice to tech pro — start learning today.