Upgrading to Windows 10 on the Surface Pro 3

Well, upgrading to Windows 10 on the Surface Pro 3 turned out to be way more complicated than I thought it would be.  I guess if I were to expand the title of this post, it would be:

The Story of How I Upgraded to Windows 10 on the Surface Pro 3, or How the Cisco VPN Client Can and Will Make Your Day Miserable.

The initial steps were easy. First, I had to get the Windows 10 Media Creation Tool from Microsoft. I chose to create a USB stick so that I could upgrade multiple computers with one download. However, if you only have the one computer to install on you may choose to skip this process and directly install.

From there, it was a simple matter of running the setup program from the USB drive and playing some Cities: Skylines while the process ran.

It took about an hour to download Windows 10 and prepare the USB flash drive (YMMV depending on your internet connection and flash drive speeds) and another hour and change until the Windows 10 desktop showed up. If things had worked out perfectly at this point, I would probably have celebrated the coming of the new age of Windows with some champagne wine beer Mountain Dew or something – but as it goes, that’s actually when things started going downhill.

It appears that the Cisco VPN Client that worked fine with Windows 8.1 is incompatible with Windows 10… and not just incompatible like it throws an error when you open it – it is EXTREMELY incompatible.

When the Windows 10 desktop finally appeared, I had no network connections available despite having all of my network adapters populating with correct drivers in Device Manager. I couldn’t connect to WiFi or tether to my phone using Bluetooth. I couldn’t use the Ethernet adapter in the SP3 docking station, or a USB 3.0 Ethernet adapter. They were all recognized in Device Manager, but nothing showed up in the list of available network connections. Uninstalling the Cisco VPN client proved futile too, in regular mode and in safe mode.

After struggling with this for a bit, I decided to just nuke the install from orbit and do a clean reset of the installation. At the time, I wasn’t certain it was the Cisco VPN client causing the issues, so I decided the nuclear option was probably the best bet.

Update: It seems like a few other users have noticed the same problem and reverting to Windows 7/8, removing the VPN client, then repeating the upgrade process fixes the issue:

Of course, starting from scratch meant that I had to rejoin my work domain, re-enable BitLocker (which ended up being the bulk of the time spent), reinstall all my programs (which was made much easier with Ninite!), re-checkout everything from various SVN repositories, and more – which ended up being a whole day of work. And the cherry on top is that since the Cisco VPN client is still incompatible, I’m unable to work from home to make up for the time I lost futzing around with the reinstall.

Throughout this process, I was left with two impressions. The first was that when it works, Windows 10 is an amazingly polished product with many little improvements to the user experience that just keep on impressing. Things like recording gameplay, seamless switching between Tablet mode and Desktop mode just by folding the keyboard around, and the new quick settings bar make me wish Windows 10 had showed up about 5 years ago.

The other impression I got was that this is far from a finished product. Perhaps it’s due to something I’ve installed that’s still not updated for compatibility (Dropbox? Google Drive? Adobe Creative Cloud?) but the Explorer process kept on locking up on me during high system activity – for example, when installing updates or encrypting the drive with BitLocker, browsing files and folders would end up freezing quite often and could only be resolved with a reboot. This meant I had to leave my main work computer alone for almost 5 hours while BitLocker encrypted the system.

After 24 hours with Windows 10, I’m exhausted and questioning whether the effort was worth it. Like Windows 8, Windows 10 shows many signs of being a bipolar/split personality operating system, and many of the transitions between the “Desktop” applications and “Metro” applications are still rough (though definitely made smoother by the fact that “Metro” style applications can now run in a windowed mode instead of being forced to full or half-screen). The direction Microsoft is going in is definitely the right one though, and I’m definitely looking forward to Windows 10.1 or whatever they’ll call it.

In the meantime though… screw you, Cisco VPN Client, friggin piece of garbage.


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