Windows SBS 2003 to 2011 Migration

I have the privilege of assisting a client in migrating from a long-running installation of Windows Small Business Server 2003 running the usual slew of SBS services & a couple of LOB apps, all on out-of-warranty hardware that's started to show the signs of old age.

Microsoft has an incredibly detailed guide covering best practices and needed steps to get the migration going. After configuring the newly purchased Dell T6600 (very few local non-profits that I've dealt with have actual hardware racks) as a Hyper-V host, I installed SBS 2011 using the answer file created on the old server. Instead of swapping disks, I just added a second optical drives to the VM, using the second one to mount an ISO of the answer file created using ImgBurn.

I was wondering why the installation was taking so long without the progress bar budging, so I opened the command prompt (using shift+F10) and ran netstat -a to see if the server was connecting to anything, which showed connections to Microsoft's update servers. After reading this post about updates failing, I figured I'd give it another 30 minutes before rudely interrupting, but by then it had finished the updates.

Next up: migrating Exchange…