I just installed sql server 2008 on my new laptop. I am attempting to connect to a sql server 2005 instance via VPN. The vpn connection works just fine. When I attempt to log into the DB with sql managment studio I get an error 40 and 53. I checked my login info and ip address they are both good. I have checked everywhere I can think and it seems to be listening on port 1433 (the remote DB is as well) My old laptop will log into the DB. When I attempt to ping the server it times out. Any ideas on what I need to fix?
If ping is timing out then SQL isn't going to work. You need to get the network working at that level before attempting to work with SQL Server.
Check your firewalls, etc. The VPN may not be configured to allow your new laptop to route to that address, but it is configured to allow your old one. Your network admin / systems admin should be able to help check this for you.