Upgrading to Windows 2008 R2 Woes

Should be relatively straight forward: Upgrade a Windows Server 2008 to R2. Hopefully, this write-up will help others avoid the problems I experienced.

Environment:
Host server: Windows 2008 with SP1 installed. Fairly clean, only 4 Roles installed:
- Hyper-V
- Active Directory Domain Services, which requires:
- DNS Server
- File Services

Primary domain server: Virtualized 32-bit Windows 2003 Server R2 SP2.
This machine has been the primary Domain Controller and File Server for many years, and was moved to a Virtual Machine around January 2008. Because the host machine is sharing the removable backup drive, I needed to make the host 2008 Hyper-V machine an AD Controller (the only way to make a host machine bootable as a domain member machine, if the AD PDC is in a VM).

To prepare for the host upgrade to 2008 R2, I easily found the article How to upgrade computers running Windows Server 2008 with the Hyper-V role installed to Windows Server 2008 R2. The article is clear that all Hyper-V guests must be shut-down, with no shapshots.

Mildly nifty: since my 2008 R2 media was an ISO file, I decided to use MagicISO to map a drive letter to the ISO image on a workstation, then share the drive-letter from the workstation. I fired up 'setup.exe' by browsing to the workstation share.

I was prompted for flavor of install (core or full), do an Upgrade/Fresh (chose Upgrade), then a system check was performed. The upgrade of the 2008 system could not continue due to 2 reasons:
- not enough C: disk space.
- could not verify 2008 R2 AdPrep /forestprep and /domainprep have been run.

Not enough space on the C: drive (14.5 GB free, 15.5GB required!!). Should be easy fix, just run the Disk Cleanup tool. Couldn't find it under Start > Programs > Accessories > System Tools... must be hidden somewhere else (the dreaded New Ways To Do Familiar Tasks). Maybe under C: - Properties > Tools? Nope not there. Tried Server 2008 help: "run disk cleanup", bullet 1. is "Click to open Disk Cleanup" (now why must I go through help to find the tool?!), but the click didn't do anything!!

After another 1/2 hour wasted looking for the Disk Cleanup tool, I first found article: Add Disk Cleanup in Server 2008, but YIKES! this adds the "Ink and Handwriting Services" service?! Now why-in-the-world would I want that added to a Server 2008 system I am *trying* to keep clean?! Ugh. Fortunately, my Google search had for the next link: Where is the Disk Cleanup tool? It's missing in Windows Server 2008!. There I found info that I didn't need to install all that other Handwriting garbage to get the Disc Cleanup tool.

Unfortunately, the Disk Cleanup Tool only cleaned up 32MB, still a ways to go for the remaining 1.0GB. Some more digging in the Windows directory, I found over 2.15GB in Windows\SoftwareDistribution\Download directory! It escapes me as to why they are retained, if these files are not required after installation. According to Microsoft KB article How to reclaim disk space on Windows XP and Windows Server 2008-based computers, scroll down to "Delete Windows update files", section "2. To delete the download cache for Windows updates, delete all the folders in the %Windir%\SoftwareDistribution\download folder that were created more than 10 days ago."

Now why-in-the-world does it make sense to retain Windows update install files after the update has been successfully installed? Or at least make this part of the Disk Cleanup Tool! I went a little more cautiously, deleting files and folders that were at least 3 months old, reclaiming 1.85GB of space!!

So, next task: running the AdPrep command. Easy enough to find the command on the 2008 R2 disc: \support\adprep. But the command failed: Adprep was unable to check the domain update status.
[Status/Consequence]
Adprep queries the directory to see if the domain has already been prepared. If the information is unavailable or unknown, Adprep proceeds without attempting this operation.
[User Action]
Restart Adprep and check the ADPrep.log file. Verify in the log file that this domain has already been successfully prepared. Adprep encountered a Win32 error. Error code: 0x3a Error message: The specified server cannot perform the requested operation.


More Google searching led me to Troubleshooting ADPREP Errors, which didn't definitively tell me the problem, but I was able to deduce that I needed to run the AdPrep command on the Operations Master system, which in this case was in a Virtual Machine running 2003 Server.

The attempt to run AdPrep /forestprep from the 2003 Server resulted in The image file \support\adprep\adprep.exe is valid, but is for a machine type other than the current machine. So the panic set in: do I need to upgrade the 2003 Server system?! THAT would be show-stopper. After a bunch of digging around (and taking a wild guess), I noticed and decided to run from the same directory 'adprep32.exe'. That command succeeded in updating the AD forest and domain structure. I forced a replication with the Server 2008 Domain Controller with repadmin /syncall ComputerName2008DC. The repadmin command returned successful, so time to shut down the 2003 Server VM.

One more pre-emptive task I decided on was to configure all of the Hyper-V guest machines so that they would not auto-start upon Host Server start-up. I had a feeling there would be a coupld of reboots in this upgrade to Server 2008 R2 process, and I didn't want the VM's to start until the upgrade was completely done. (That would be really nice if there was a Hyper-V command to temporarily disable start-up of all guest machines, changing the start-up properties for 7 VM's was a pain.)

I double-checked C: drive free-space, 16.9GB, good-to-go. Fired up setup, checked for on-line updates, chose the Upgrade option, setup began copying files.
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