My customer currently blocks outbound RDP and SSH, which means that none of their employees can get access to external Windows and Linux boxes (at the console level). However, a need has recently arisen to give access to an assortment of RDP and SSH endpoints scattered throughout the internet. The endpoint IP addresses are a moving target, and an access list exists to define what those IP addresses are.

So now my customer wants to have a single Windows Server that they control as the sole outbound point for RDP/SSH to the internet. Consider it a jump box to the internet. If one of our admins have an access to this Windows box then they can log on, and from there bounce around to RDP/SSH endpoints on the internet.

Is a standard Windows 2008 box going to work as a jump box? For example, I seem to recall that Win2k8 limits the number of users that can log on simultaneously, which means that the jump box may not be accessible if lots of users are on it. Advice as to how to make this work..?