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I have a user who is connecting through a VPN and then RDP’s to a server using it’s public address. He is not able to connect to the RDP session from his main PC. He can, however, connect from any other PC (they are all windows 10 pro) without any issues. On his main pc he can’t even get the credentials box,

I have not tried removing the checkbox on IPv6 setting on the NIC as I doubt the other 3 machines he has done this on have this setting unchecked as well.

The IP address is correct, his domain his correct and he does have network/internet access.

I am unable to check if he can connect to another server as there is no other server available for him to connect to anyway, as in none that he is allowed access to.

I have also taken his credentials and tested on my own (win 7 pro) machine and had 100% success.

Any thoughts?

1 Spice up
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Is the antivirus software on the server only allowing specific subnets to access via rdp?

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Check the antivirus just as Bezoid has mentioned, and if possible check to see if his firewall is blocking the RDP port.

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When he connects from the other (working) computers is it also through a VPN?

Random question, why attempt to RDP to a public IP address if connecting to a VPN, couldn’t you use a local address if you are VPN’ing in?

Does anyone else RDP through the VPN like this? Is there any specific firewall rules preventing the connection? What about trying the FQDN of the server, perhaps there is a DNS issue.

1 Spice up
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What VPN device is setup? Cisco, Sonicwall ect?

Can he ping the server from his computer?

Can you ping the server from the VPN?

Can you ping his computer from the server when he accesses the VPN?

Like epiepenburg said does anyone else RDP through the VPN and runs into the same issue? This will help figuring if it VPN box issue or his personal computer.

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It’s a Sonicwall vpn.

yes I can ping the server address while connected via vpn. the user is remote to the server so his pc is not on the domain network so pinging the server address from his computer won’t work

All other users are able to access the server via VPN without this issue

EDIT:

I take back what I said about being able to ping the address, I thought we were able to but we were not, just tested again tonight. And now there is a 2nd user who cannot connect. Very stange because there is a whole team in India from the same company as this user who have no trouble connecting to this RDP yet the 2 users in the US (the server they are connecting to is in NY) can’t connect.

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I am not 100% sure of how the network is configured. They do need to use the public IP to access the server, though I agree with you on that. Although, he mentioned to me that the other users are using the same IP. I’m not sure how their VPN is set up. I do know that they have to browse to something like vpn.domainname.com to login. Perhaps is configured to connect only to the public IP?

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when connected to the VPN even from a non-domain machine you still should be able to ping the server via its FQDN.

What are the odds this person has hard-coded a DNS address for their network connection?

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To all who have commented:

I have done some extensive troubleshooting on this issue and appreciate everyone’s responses. Unfortunately It is still unresolved at the moment. I have tried all of your suggestions but I have also just found out that there is now another user who is unable to connect as well. The client and myself are going to get on a call with the IT department at the company of where this server is located and try to figure out what the issue is.

Thank you all for your help. I will post the answer to the issue as soon as I am able to resolve it. If you have any other suggestions definitely please post them. What I have done so far is this:

From my users work laptop: can’t ping the IP of the server or FQDN, checked to make sure he doesn’t have an DNS addresses hardcoded on his wifi or Ethernet nics, compared the settings of his VPN connection to the settings of the same VPN connection on my laptop (the same), Couldn’t connect even as a different user logged into the machine,

From my users personal laptop and my own laptop we were able to successfully RDP to the server.

I did notice he had a VPN network connection for a different sonic wall vpn connection but I was unable to remove this. I wonder if it could be causing the issue, and I wonder if the other user having the problem connecting has the same other sonic wall vpn network connection as well. It is disabled but maybe something causing problems?

Thanks again!