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Can't access on-premise server from VM in Site-to-site virtual network

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Hi,

I have configured a Site-to-site virtual network in order to connect our Azure VMs with our partner's on-premise network that hosts some services we need to access.

The virtual network seems to be ok... everything looks ok in the Azure portal and I was able to create a VM in that network without any issues.

I can even ping the on-premises server from the VM with no problem.... The problem is that I cannot access the web services that're hosted in this on-premise server.... I just try to access it by using the URL (using port 8085) and I just get a timeout.

I've configured the VM's firewall with an outbound rule on port 8085.... and I have requested our partner to ensure the port 8085 is accessible from our virtual network private ip range. They have confirmed the port is open as they have even created a loopback in the VPN device to test whether incoming connections from our IP address are allowed.

So, right now, I'd like to know:

1. What can be happening here? What else should I look at?

2. What can I do to diagnose these connectivity issues? How can I find where's the problem now? 

3. Why can I ping the remote on-premises server but when I try to telnet on port 8085 it doesn't work (and the remote 8085 port is open)?

I'd really appreciate any help on this issue!

Thanks,

Rodrigo.


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