Exchange Server Telnet Test

OK. I give. For years and years and years everyone always references telneting to an Exchange Server for testing the SMTP. I have never been able to do it. I have a Windows 7 x64 box with telnet installed. I open a command prompt and type in "telnet mailserver 25" get the error that the connection could not be opened.

I am doing something wrong and have been for years because I have never been able to get teleneting to work to an Exchange Server. I have even tried with Putty. What am I doing wrong?
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Will SzymkowskiSenior Solution ArchitectCommented:
Port 25 is probably not allowed from your client machine that you are using. Most likely restricted. Try using Port 587 (client side port)

telnet 587

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LockDown32OwnerAuthor Commented:
Same results. Unable to connect. What do you mean port 25 is most likely restricted? I set up the Exchange Server 2003 and did the port forwarding through the firewall. It is working like a champ but I can't do the telnet test.

I read something somewhere that I needed to allow relaying from my IP. Did that too. Still no luck.
Will SzymkowskiSenior Solution ArchitectCommented:
You are trying to telnet from a workstation Win7 to Exchange server (internal on the same network)?

Do you see anything in the logs on the server?

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LockDown32OwnerAuthor Commented:
I was doing it from my computer on the internet. I tried it on a local computer and it worked. Since port 25 is forwarded from the internet why couldn't I do it from the internet?
Will SzymkowskiSenior Solution ArchitectCommented:
Port 25 is for server to server communication over the internet. Have you checked your firewall logs? This will tell you exactly why it is failing. Telnet is probably not an accepted service on your firewall.

LockDown32OwnerAuthor Commented:
That is interesting. I was under the impression that firewalls worked on Ports and that it was allowing and forwarding port 25. So it actually not only allows based on port but also on service? How does the firewall know it is the Telnet service?
Will SzymkowskiSenior Solution ArchitectCommented:
You are using Telnet over port 25 for communication. This is not straight port 25. That is why it is not working. As I suggested check your logs and you should clearly see where it is failing.

However because Telnet is being blocked from the Internet is a good thing. Telnet does all transmittion in clear text.


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