Last week we moved the crawlers from our office to a real data center where we can get more, and more reliable, bandwidth. Getting everything installed and working wasn’t too much trouble, although the next time I have to do something like that I’m going to do a lot more pre-installation work here at the office before taking the machines to the data center. Installing and configuring 10 machines while standing in the cold, noisy data center isn’t my idea of a good time.

Having machines at the data center means that we need some way to log in and check on them. Not a problem, as the Cisco security appliance we bought supports VPN. And configuring the Cisco IPSec VPN was quite simple. I was pretty happy when, with just an hour of looking at the documentation and fiddling with the configuration, I was able to log in to the VPN from my laptop. I packed up my stuff and headed back here to get everybody set up to use the VPN.

And then I found out that Cisco’s IPSec VPN client won’t run on 64-bit versions of Windows.  Nor does Cisco have any plans to upgrade it.  Since I’m not willing to create a 32-bit virtual machine just for running the VPN client, that leaves me with the option of configuring the router for some other type of VPN.  And there things get difficult.  The documentation that came with the router doesn’t discuss any type of VPN configuration other than IPSec, and the online documentation I’ve seen makes the assumption that I understand everything there is to know about VPN.  It gets confusing in a real hurry.

There are VPN standards.  There are so many, in fact, that no mere mortal can begin to understand them.  It might as well be a free for all with all those competing protocols.  Just the acronyms are enough to push a questionably sane person such as myself over the edge into babbling lunacy.  I’ve yet to find a document that explains, in terms a reasonably bright person who hasn’t passed Cisco’s certification can understand, how to configure the VPN.  I can’t even find a good discussion of the benefits and drawbacks of the different VPN technologies:  IPSec, L2TP, or SSL.

I also need to configure VPN on our pfSense box here at the office.  That looks almost as daunting as the Cisco’s configuration and the documentation is, if you can imagine, even worse.

I realize that much of my frustration stems from my lack of expertise in this area.  I’m a programmer, not a network admin.  But I have to think that VPN just doesn’t need to be this hard.

I can find lots of “how VPN works” types of discussions online, but they’re presented at a very high level.  There also is plenty of detailed documentation about VPN configurations for very specific situations.  But I’ve found nothing in the middle.  Something like “Simple VPN configuration for people who don’t live and breathe this stuff.”

Pointers to good discussions of the different types of VPN, and good tutorials about configuring VPN on the Cisco ASA or pfSense would be greatly appreciated…