1. I have always found its best to install from scratch, although upgrades have improved since the days of Windows 95/98 its always better to do fresh install to ensure full compatability with everything (drivers, etc..).
2. Windows 2003 has RRAS which can support VPN connectivity. Its going to be better if you are utilising this for outside connectivity to install something like ISA Server to secure the connectivity further. Also, there are dedicated hardware devices aswell that can provide this. SSL VPN is an upcoming technology, but it depends what you plan to use it for.
Yes that should be ok, my only question would be where the VPN users are coming from ? I would not recommend installing Windows 2003 directly on an Internet Link without some for of Firewall (although you can harden the Win2003 server, its still not ideal).
Currently, their server is only behind a normal Linksys router with no firewall. I have already explained the need for a firewall. They currently have remote access (RDP) available to the server. Would enabling VPN be any less secure than it already is?
Re: Upgrade from Server 2000 to Server 2003
11 years 5 months ago #23302
VPN would be more secure as you can do much more on the encryption and Authentication then with just RDP. Is the router just an ADSL Router which NAT's everything and you have had to setup port translation ? Its much more difficult to configure VPN connectivity if you are dealing with NAT anywhere on the link as thats part of the security built into the VPN. They do have NAT-T which can simplify the VPN connection over NAT devices and also if you make sure you use ESP and not AH you will be ok. AH is pretty much redundant anyway because ESP can also do Authentication along with Encryption.