Able to RDP into remote server, but not able to ping or telnet - windows-server-2008

Question

We have a Win Server 2008 box being hosted (dedicated) for us.
I need to connect to one of it's DB's from a server in our LAN.
What started out as a "sure, I'll just throw that together for you real quick" project has turned into a week-long hair-pulling pile of WTF :)
I am able to RDP into that server without fail or issue.
When I tried to connect to the DB, I got a generic "could not connect" error, so I went hunting.
Telnet attemtps and pings time out.
Since then, we have tried endless variations of firewall settings (including wide open), and still ... no go.
In addition to our firewall, the hosting provider also has a firewall layer.
We turned on all logging, and we don't even see any connection attempts at our FW.
We then had the hosting provider turn on all logging, and they don't see any connection attempts either!
Hrmmmph
I'm at a complete loss.
Any suggestions?
BTW, while I'm comfortable enough with all this to explore and make changes, my experience with firewalls and stuff is fairly limited, so don't hesitate to dumb it down ;)

Answer 1

It is hard to give just one answer to this question, because the interim results of the problem analysis lead to different steps that you need to do next. It will more likely be a step by step help with tracing down the problem.
Do not trust any firewall setting (esp. not any that someone else did, and again esp. not if you don't know him), unless you tested it. Firewall settings are tricky and even experienced professionals get them wrong now and then.
In the guide below, I will write <win2008server> in commands where you have to put the name or IP of the windows 2008 server to which you want to connect. On the other side, I will use the expression "office PC" when I mean your workstation PC in the office from where you are trying to connect to the win2008server.
STEP 1: Checking the Endpoints
1.) Can you telnet to the RDP port?
On your office PC, try this on a command prompt:
telnet <win2008server> 3389
This is to make sure that DNS name resulution works for telnet, as well as network hardware and routing. It should, because you can use RDP to establish this connection. However, anything can get in between, like the telnet command being in any way configured nonstandard or being replaced for whatever reason on a company pc (sysadmins have strange ideas at times...).
2.) Can you telnet locally on the win2008server to the database?
When logged in using RDP on the win2008server, open a command prompt on the server and issue the command
telnet <win2008server> <database port>
That means you are trying to connect from the server to itself. This is to make sure the database port is open on the server.
STEP 2: Checking the Firewalls of the Endpoints
If for 1.) and 2.), your answer is yes it works, you have to test if either the remote side can not be reached or your location can not connect to the internet on the port you are testing (database port). You do this by replacing the respective other side with any other host on the internet for which you know it's reachable or can reach other servers. Typically, you google for a port checker ;)
3.) Check if the win2008server can be reached from another location than yours:
3.1.) Check if the RDP port of the win2008server can be reached from a third party location:
Google for port checker and take the first result (e.g. http://www.yougetsignal.com/tools/open-ports/ ). Type in the name or IP address of the win2008server and the RDP port, usually 3389 . Click on "check" and wait for the success or the timeout.
3.2.) Check if the database port of the win2008server can be reached from a third party location:
Do the same as in 3.1.), just with the database port instead of the RDP port.
4.) Check if you can connect to an outside server on the database port:
For this to work, you need to know a server or create one, which is somewhere outside on the internet, and which listens on the database port. You typically do this by keeping your private PC at home run and accessible through RDP or SSH, and there you open a server and configure your private internet router to forward the connection correctly.
Another way to do this test is webspace with SSH access. Many webspace providers nowadays allow for an SSH login (usually any webspace at $4/month and above).
Let's assume you have SSH access to any such third party place. You can use nc (netcat) there to open a server socket on the database port with this command:
nc -l <database port>
If it's your private PC at home, you usually have to also configure your private router and set up a dynamic DNS name for your internet access for the whole story to work out. You do not have this extra work with a webspace based SSH login. However, there you can not test ports below 1024 because you do not have the privileges. Good luck with this ;)
After you got this, try connecting to the port that you opened:
4.1.) From your office PC with
telnet <third party location> <database port>
4.2.) If 4.1.) does not work, also try with the port checker, because you might have gotten something wrong with setting up the server. Look at 3.) for this, and use the <third party location> and <database port> with the port checker (fourth party check).
STEP 3: Blaming ;)
At least one of the things should have failed by now and you can start calling people and letting them know about your tests and the results. You should be able to combine the results logically, but never start with that. Think about how to convey the information. Start out with your findings and then let them have a moment for their own conclusion. It can be difficult to tell someone in another company or department that their firewall isn't configured correctly. They might deny this even in the presence of proof. Be patient. Explain your findings again. Hint at the conclusion. This can be the trickiest part of the whole problem solution.

Answer 2

I have to say that today I had the same problem.
My solution was just to edit secpol.msc and disable all the FW profiles; then, run services.msc and also disable Windows Firewall service.
After this server was pingable for me.