Upgrading SBS 2003 to SBS 2011

So, we’re at a client’s and we have to do a migration from SBS 2003 to SBS 2011.

We’re relying on Microsoft’s instructions to get us through the night.

It’s 7:31 pm on a Friday night.  The air conditioning in the office has been turned off, so it’s a bit sultry.  I prepped the source server last night — just made sure its service packs and patches were up to date.  Now that I’m on site, I’m ready to make my answer file.

To do so, we need to install some tools from the SBS 2011 install media (which happily Dell included).

Sadly, the pre-requsites to using the tool don’t run on Windows XP, and this is an XP shop.

Great.

However, I’ve got two Dell Inspiron 560s ready to be dropped down and they have Windows 7 on them, so let me unbox one and get it powered up so I can get the server migration started.

(I had planned on installing the workstations when the data was migrating… looks like I get a jump on it…)

I’ll be back once I’m unboxed…

 7:56 – Machine unboxed, Facebook notified of liveblogging, OOBE completed, waiting for my desktop customizations and personal settings to be applied. Backup of source server in progress.

8:22 – Machine joined to domain, Migration Assistant installed and waiting for backup to finish…

8:31 – Backup can take 7 hours.  Uh-oh.  Wait!  The server is running in a VM!  There was a hardware failure which precipated this migration so we brought the old box back up in a VM.  (Pretty slick apart from a couple licewnsing activation gotchas.  “DRM — Screwing the honest since 1998.”) So, I can just take a snapshot and roll back if anything goes horribly wrong! Score! Back on schedule!

8:37 – Migration Assistant found some issues…

9:08 – Issues persist.  Odd ones  that aren’t true – the remote registry service IS running, but the migration assistant refuses to believe it…

9:51 – Ran some more hotfixes on the server after SBS BPA suggested it.

10:16 – Re-read some documentation.  Last night, I read that (what I thought was) the migration assistant needed to be run on a workstation, not the server.  That does not seem to the case.  I’ve spent the last hour chasing down ghosts.

10:20 – Running the MA on the SBS server worked right out of the box.  FML.  Wasted all this time due to my stupid brain.  Stupid, stupid brain.

LESSON 1: Run the Migration Tool ON THE SOURCE SERVER.

10:42 – Answer file created, copied to USB key, USB key in destination server and the install is now running on the destination server.  Right out of the box, the new Dell server runs thru its little preinstall and then dumps you at a screen that says “Basic or Migration Install?”  I choose Migration, it reads the answer file like magic, and we’re off to the races.

I created the answer file to not be unattended. I like clicking NEXT when I do my server installs – just to make sure everything is right one last time before committing.  Good thing too, since I misspelled the domain name on the credentials section of the answer file…

Now we wait what may be 30 minutes for Windows to expand its installation files…

10:53 – Server just rebooted itself…

10:54 – Seemed to apply some updates, back to waiting for expanding files… and in the time it took me to type this, it started rebooting again… and we wait some more…

11:02 – Finally, motion!  The bar on the screen started moving across.  I guess all the updates are done… more waiting…

11:03 – I guess it connected to the domain because a printer mapping came up and failed due to an incompatible driver… more waiting…

11:31 – 80% of the way thru the bar.  “Up to 30 minutes,” indeed!”  Luckily, the new workstations (before decrapifying) have the WildTangent games on them.  They’re usually the first things to go, but right now, I’m glad they’re here…

11:43 – 90% of the way thru… when does the 6 hour “migrating data from old server” start?

11:44 – No sooner than I type that, then Explorer starts putting up its “Customizing Browser Customizations…” dialog, and the SBS Setup program quits with an error.  Swell.  (Looks at logs… might it have something to do with time synchronization?!?)

12:12 – Fantastic.  The source server got hung up (a backup started: LESSON TWO – STOP TASK SCHEDULER) and the clock stopped advancing, which caused Kerberos errors, and then the only way to recover is TO START OVER.  So, rebooted both servers, booted off the DVD on the destination server, reformatted the partitions and am now sitting thru the whole thing again.  Sloppy… but this is why we flat-rate server installs… my mistakes are my own and come out of my end, not the client’s.

12:41 – We’re back at where we were at 10:42.  Lost almost 2 hours ot the minute.  Dang.  Worst part, is I don’t have a key to the building, so I’m trapped here.  Can’t even go out for a bite and come back…

1:08 – Server install fails with “JoinDomain_DCPROMO Failed…” – turns out the initial failed install got as far as seizing all the roles from the other server and was already in the domain.  So, instead of trying to reverse everything I did, I just reverted to the snapshot from 8:31.

1:22 – Snapshot still had the anti-virus installed and didn’t have the migration assistant run, so we’re waiting for the post-AV, pre-MA reboot.  *sigh* I’ll be pretty good at this when I finally get it done… tho I am ECSTATIC that the server is a VM and all it took was the snapshot to roll it back.  I don’t know what I would have done (likely a clean install, then a manual migration of mail and a visit to all workstations to rejoin them to the domain) if I didn’t have that capability…

4:19 – Been a while.  Had to give two it more tries.  Both failures.  This last time, I logged in to the domain once as the new user they want you to create to act as the migration account, and maybe that was the charm, because now — seven hours after we started — I can proceed to STEP FOUR of the 19 Step Migration document…

8:34 AM – Looked good for a while, then it didn’t.  The Migration Wizard on 2011 isn’t as automated as one might hope, and in my bleary eyed state, I made some missteps and by the end, nothing seemed right, so I punted.  Old server restored from snapshot and I will take another run at this soon, once I catch up on some sleep and more reading in the migration guide.

7 thoughts on “Upgrading SBS 2003 to SBS 2011”

  1. Hi. I am eagerly awaiting the next installment of this saga. I did 1 SBS 2003 to SBS 2008 and it took weeks till I could turn the thing back to the client. Now other clients are looking at 2003 to 2008 or 2011 migrations and I want to know how others went.
    Thanks,
    Ben

    1. Long story short – punted. Rebuilt the domain from scratch, used Exmerge to dump the databases and reimport them into the new store. I was not impressed with the whole process. I’ll write something longer up soon.

  2. i am in this hell – 4th attempt failed again at the exact same spot – I mean, what exactly is InstallCrimsonManifestTask? DCPROMO, share point etc all look fine. RDP bust but fixable and there seems to be permission issues to random event logs for the event log users group. It looks like in real terms the install fails at installing the Exchange 2010 mailbox role, then it goes tits up from there. The source server I have went over all weekend so far and everything is perfect – I am at a loss.

    Rip up and start again is not an option – 3 DC’s, 2 Exchange servers in 2 cities – 45 users. I have to say that any 2003 to 2008 migrations I have done in the past have been fairly smooth however the 2011 Migration assistant smells of not quite ready for the real world complexities. Awkward conversation to be had in the morning with client – I don’t like the things did not go according to plan conversation, I have tried everything I can however.

  3. I’m currently watching SBS2011 install on a horrifically fast box…but the install progress bar has been sitting around 5% for the last hour, complete with multiple reboots.

    It’s also funny how Microsoft forces you to provide an answer file that can only be generated from your previous Windows SBS server…but when you provide the answer file to your Windows 2011 box, it simply pops up a dialog prompting you to confirm all the info….so why not pop that box up in the first place and skip the hassle of downloading and installing all the tools required to run the answer file tool? I really *hate* Microsoft. I’ve ‘wasted’ 3.5 hours and the server is nowhere close to being finished.

    Contrast all that with another client I have. I upgraded their mail, intranet, instant messaging, and file storage server yesterday. It took me about 30 minutes. I just typed ‘do-release-upgrade’ into their awesome Linux server and then rebooted 30 minutes later. Everything worked flawlessly. The only cost to the client was the small hourly charge for my time…

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