Microsoft Surface Pro running DirectAccess!

I recently had the opportunity to acquire a Microsoft Surface Pro. My everyday laptop has a fairly small screen, I did this on purpose for traveling and ease of use, and so at first I was a little skeptical that I would make much use of the Surface. It seems I was wrong. The Surface is considerably easier to take with me, and much faster to pop open and quickly check on emails or documents or whatever I need to do on a PC. “On a PC” That is the key here. This is no standard data consumption tablet device that is really only built for reading emails and news feeds and playing games (you know what I’m talking about). This is full Windows, and as such I am able to install and run anything that I would on my laptop. It could truly replace it.

Because I’m running full Windows, I can also use it to VPN into work. Nice, but who wants to launch a VPN??? Lame. Since I have pretty much a one-track mind, that track being DirectAccess, I of course had to find out whether or not I could get my Surface Pro to be continually connected to work without needing to do anything. The only problem that I could see? This is a “Surface Pro”, not a Surface Enterprise. Unfortunately the Pro version of Windows 8 does not comply with the requirements for DirectAccess connectivity, and even more unfortunately they have done away with the Ultimate SKU in Windows 8, so no joy there. My only shot at getting DirectAccess connectivity is to bring this Surface up to Windows 8 Enterprise.

I did a little research, and found some folks who had done it. It didn’t look like the most fun thing I have ever done, but I was ready to give it a shot. I happened to be traveling at the TechEd show when I got the Surface, and I had with me a Windows 8 Enterprise x64 ISO file as well as a USB stick. I was fully prepared to create a bootable USB and completely reload Windows to bring it up to Enterprise. I even found a link to Surface drivers and had them with me as well, because I figured it would struggle to recognize all the hardware in that guy.

Before starting that whole process, just for fun I attempted to run the feature in Windows where you can simply enter a new product key and Windows will do an in-place upgrade. I have done this successfully on Windows 7 Home Premium machines before to bring them up to Ultimate for the purposes of DirectAccess, and while I didn’t think that it would work for Enterprise, it was worth a few seconds to give it a shot. This option is the one inside System Properties, where you click on the Get more features with a new edition of Windows link.

“This key won’t work. Check it and try again, or try a different key.” This is the message I got. I tried multiple keys for Windows 8 Enterprise, but they all did the same thing. So this wasn’t going to work. At this point I copied the Windows 8 Enterprise ISO that I had with me onto the Surface in preparation to use it while creating my bootable USB. Then, almost by accident, I double-clicked on the ISO file. Inside the ISO, I looked at the file called “Setup”. I double-clicked on it. It launched.

I clicked on the Install now button, and setup started rolling! I was still hesitant that this was actually going to do anything in the end, but I went along with it. After accepting terms, I was presented with the “Upgrade or Custom Install” screen. I chose Upgrade, and voila.

Setup ran through some screens, it took maybe five minutes, and after rebooting, my System Properties now show that I am running Windows 8 Enterprise, on my Surface Pro!

Boy, that was easier than I thought it was going to be. Now that I was running Enterprise, all I have to do is join it to the domain and get the DirectAccess connectivity settings onto it. Since I was sitting in a hotel room at this point, I used VPN to connect, and over that VPN I was able to successfully join the Surface to my domain, grab a certificate from my CA server (we require cert authentication for DirectAccess), and pull down my Group Policy settings. After one more restart, DirectAccess is live on my Surface Pro!

And of course since DirectAccess is so awesome and seamless, I was immediately able to log in as my domain account while I was sitting right there in the hotel room. Nice!

Jordan Krause