Lately I’ve been building and dropping dev / test virtual machines at an alarming rate. I prefer not to use images for purity reasons, so I end up installing the OS from scratch then installing all the updates usually before I even join it to the domain.

The single most time consuming process is getting updates installed – both for the time it takes to complete, and the interaction required to see it through to completion. For example, Windows Update offers and enabled IE9 on first update. For some reason, they decided that the IE9 installer must be interactive. Windows update installs the first 80% of the updates, gets to IE9 and sits there waiting for you to click “OK”. Lame.

Another annoyance is that in order to enable Microsoft Update you must first select an update option, which kicks off an update search. Then when you enable MS update, it forces a rescan.

So, here is my procedure for getting a server up to date in as few step as I have found.

1. After first boot: install your VM tools / drivers. Reboot.
2. On second boot: Set your timezone, adjust network settings (i.e. disable ipv6 if so desired), enable remote desktop, disable IE ESC, adjust screen resolution. Then:
   1. Install the .NET Framework 3.5.1 under .NET Framework 3.5.1 Features in Server Manager (Note – not the whole feature – this installs IIS and such)
   2. Open IE and download the .NET Framework 4 full web installer (I just search for “.net framework 4 web full” – it is the first result) and run it
   3. Install IE9 (again, search for IE9; make sure you uncheck the box to include Bing)
      Note: these first three are installed first because you will probably need them, and it avoids unnecessary IE8 updates from being installed when you are about to replace it. It also lets you kick off the update and walk away for a while knowing that when you get back they will just be done (instead of waiting for your confirmation)
   4. Open windows update (type “update” in start box), click Change Settings, select Never install updates.
   5. Now you can click the link to enable Microsoft Update – it should go nice and quick and probably will kick off your first update scan
   6. Might as well make sure all the updates are selected (server 2008 r2 doesn’t include the Activation Hardening update that Windows 7 gets, and I usually hide)
   7. Install updates. Will take at least 20 minutes. Reboot
3. On third boot: Don’t trust windows update, force an update check. It will find more, including some .NET 4 updates that take FOREVER to install. If the updates do not demand a reboot, run another update check, install. reboot as necessary, repeat until it finds no more updates.

It still takes way too long, but it shaves a few minutes / reboots off the update process.

Yes, I know this could be done once, the install sysprepped then imaged. Trouble is, I don’t have a decent disk imager other than Windows Server Backup, and you cannot sysprep before running WSB. Also, I don’t always use the same size drive.