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Can anybody help shed some light on the current issue I am facing?

I have a pfSense box running openVPN. My laptop can connect without a problem to the VPN as well as the internet. The only IP within the network I cannot ping is the DNS Server (Windows 2016). My laptop connection has been given the ip of the DNS server.

I have the openVPN server set to include: DNS Default Domain (True) DNS Default Domain: Medicore.Lan DNS Server Enable (True) DNS Server 1: IP that is unreachable.

Any ideas why this one IP, in particular, would not be accessible? The subnet for the network card is 255.0.0.0.

Edit: nslookup Results

C:\Users\David-Laptop>nslookup \fileserver DNS request timed out. timeout was 2 seconds. Server: UnKnown Address: 10.10.10.10

DNS request timed out. timeout was 2 seconds. DNS request timed out. timeout was 2 seconds. *** Request to UnKnown timed-out

Dave B
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  • It can be as simple that the server itself (due to OS / local firewall settings ) doesn't respond to ICMP echo reply packets. Do the actual services on that server respond? – HBruijn Jul 16 '19 at 08:49
  • When I am connected on the lan the server responds. – Dave B Jul 16 '19 at 08:56
  • Is openvpn configured as bridged vpn or routed? If it's routed, do your hosts have all necessary routes? Also, if it's routed, your client lies in a different network than server, so firewall on the server might be set up to answer to packets from lan and to not answer to packets from other network. – Nikita Kipriyanov Jul 16 '19 at 10:40
  • Why do you need to ping the DNS server? – joeqwerty Jul 16 '19 at 11:38
  • Because its also our AD server. We have A Records set up to resolve network locations. – Dave B Jul 16 '19 at 11:41
  • Being able to ping the server doesn't tell you anything about whether or not AD and DNS are working. Are you experiencing AD or DNS problems? – joeqwerty Jul 16 '19 at 14:15
  • I am just not able to resolve hostnames that have custom A records in the DNS. – Dave B Jul 16 '19 at 14:17
  • OK. Troubleshoot that problem. You'll waste a lot of time chasing why ping doesn't work (it doesn't by default). Have you used nslookup to troubleshoot DNS? – joeqwerty Jul 18 '19 at 02:10
  • I have tried nslookup and added the results to the question. I can see the Tap Adapter gets the IP of the DNS server in the properties. – Dave B Jul 18 '19 at 19:54

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