I must be getting soft. For the first time since DOS days, I upgraded my main workstation computer from one major operating system to another using the Upgrade path rather than the clean-install path. I guess my perfectionist ways are succumbing to the more pragmatic approaches. On the whole, the process went very well. It took over four hours, but when it was done, I had my workstation back with most of its configuration in tact but with the new OS. This post describes some of the issues I encountered as well as some positive surprises.

First, based on the Upgrade Advisor and on feedback from another upgrade experience, I had to uninstall two applications I use frequently: VMWare Workstation and Daemon Tools. This seems reasonable, since both products use custom drivers to emulate system hardware. I was able to install both products after the upgrade with no problems. Even the VMWare Workstation license and configuration was maintained. If you're using Daemon Tools on Windows 7, be sure to install the SPTD 1.62 or later _first_ and then ignore the warning that Daemon Tools is incompatible. It works fine for me but YMMV.

After the upgrade, I found that many of my symlinks were gone. This caused a number of my applications to break, but since I know my systems well and I create these symlinks on other systems frequently, I hadn't lost anything critical.

The next issue arose when I went to connect my media center (XBMC) to my system to watch movies yesterday evening. I turned on my set top box and pointed it at my movies share, and it prompted me for a username and password (which is normally cached). Turns out the problem was pretty simple. Although Windows maintained the network shares on the machine, it reset the permissions on the files. After re-authorizing the media center account, I was able to connect to the shares again.

I've also encountered some minor issues with focus follows mouse and the private status of VPN network connections without a default gateway.

Despite these minor issues, the experience was generally good. Windows updated IIS, including the WebDAV functionality, which was previously installed by a hotfix (I use WebDAV to host my own XMarks bookmarks and passwords). Almost all of the 160 programs in my Add/Remove Programs control panel were kept in tact by the upgrade process. Microsoft engineers missed a few edge cases, but on the whole, the upgrade process was smooth and a huge time saver.