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Ahh, my favorite subject these days, one which I spent weeks preparing for and three overnights achieving. Then another three overnights a few weeks later to get the SBS03 to SBS 08 going. I don't have a blog, maybe I should but there are so many.
First I did an off-site off-production redeploy and tested the upgrade, that took a few weeks in my spare time, it worked. Read the CRM IG a bunch of times, notice how weak it is on redeployment.

Then I gathered all the ducks and tried to made them walk in a row.

On a Friday evening at 5:30pm I started with full server backups including cold images, with database backups on top. Licenses and software in hand. I had CRM Small Business, but this doesn't mean you have to use Small Business Workgroup for the upgrade, we have 9 seats and they go to Professional. Check your licensing. In fact, I could not use the 4.0 Workgroup Server install media for the upgrade, it had to be the Professional media from eOpen.

You are upgrading your SQL 2000 sp4 default instance to SQL 2005 sp3, if you don't have to, don't bother with the rest (is there anything else?) of the SBS 03 R2 upgrade. Have SQL 2005 SP3 on hand unless you don't mind a 300+mb download.

If you use the default settings for Report Server you will whack your SBS default website because of ASPNET settings which means RWW, Companyweb and OWA so you decide if you know enough to configure the Reporting Service non-default or fix the SBS default site afterwards. The default Reporting setup is easier unless you have experience setting it up non-default. To fix the default sites later, when you are finished moving CRM 4 off SBS you delete the reporting service websites and set all the default websites back to ASPNET 1.1 then you should be able to restart them and then start up the default application pool. Your SBS sites should magically reappear and give you that warm fuzzy SBS03 feeling.

Run the SQL 2005 upgrade, run the SP3 (SP2 is required anyway). Check your CRM, run a set of backups at this point. Maybe run around the office and do workstation backups while your waiting for the server backups in order to prepare for when your SBS 03 to SBS 08 migration fails. Maybe do some of that system documentation, I got out the labeler and used up a roll labeling things.

OK, now you can run the 3 > 4 upgrade. Zoom. LIke Leon says you need to use the same install account that was used for the v3 install. Service account is network as per IG. Throw salt over your shoulder or something. If the off-site check worked you should be OK. Actually I had to do a regedit from PSS to get past a collation error in test and I had to do this for the production as well. If the upgrade goes you can boot and go check CRM 4 for function and see how it is so worth it. If not you get to cry and swear and stomp around what is hopefully an empty office, rollback to your previous state and get ready to send the install logs off to PSS on Monday morning, and/or spend the next few hours searching the web for why yours didn’t go. Then install CRM 4 rollup 1, rollup 2 if you dare (Personally I am waiting for RU2 to settle down) Save your databases.

Uninstall the Outlook CRM 3 clients from all the workstations. Install a new CRM 4 client run Rollup 1 on the client (In Vista you have to Run as Administrator) Check for function. If you have the time to complete the member server wait until it is done before doing the rest of the clients since they will have to be configured for that server, not this SBS box.

I had to add a DNS entry alias so that the Outlook client wouldn’t fight over cookies with the web client just like in v3. If you have Outlook open, the web client will not show a couple menus so I added a different Cname than the CRM box that pointed to the CRM box so that the Outlook client is installed with the default http://CRMBOX:5555 but the web client is set to point to http://crmCname:5555 that way they run side-by-side nicely.

Whew, now on to SQL 2008? I did this after the move to the second server, but unless somebody squalks about it I don’t see why you couldn’t continue the process on this SBS box. Do your backup thing yet again, run the SQL 2008 upgrade and hopefully you then have your CRM 4.1 SQL 2008 databases hot in hand

Guess what? Run another set of backups here and make sure they are solid. Here is where I would try to run the SBS 03-SBS 08 migration. If it goes you are in sweet and can proceed to work on your member server, if it doesn’t go you will need to restore the pre-migration backups and figure out what to do next. You can proceed to process CRM to the member server, but know that the member servers relationship to the SBS domain depends on the migration success. I chose to build a new domain when the SBS migration failed, that included rebuilding the member server to the new domain.

When you have your member server built up with Win 2008 and joined to the domain you can install SQL 2008. Pay attention to service accounts, collation and all the stuff that is required in IIS and file services as per the IG and reference docs. I got it running on a domain user account, but it seems like the first thing PSS does when there is a problem is change to a system or network account.

When you have SQL and Reporting services working you can install CRM 4. Use the SQL default instance unless you want to fool around with config.xml files to get the reporting services connector to work. DO NOT attempt to attach to existing databases at this time, you will be importing the organization later, instead, create a temporary organization that is called something other than what you want the final org to be named. You are installing a blank working rig at this time. Boot and check that this blank org is working, then you create and restore your COMPANY_MSCRM database and import it using the CRM 4 deployment tool by running Import Organization which maps the users and stuff. Yay. Check for function, data, and how any customizations are working. I hear you have to rebuild workflows here, not that I know anything about that.

Now you can run around and install the v4 client and rollups on the rest of your workstations as well as rerunning the config wiz on that single test workstation you did awhile ago. When these are up and running clean you can go back to your SBS box and uninstall CRM, SQL, Reporting and get the SBS default sites back. Yay.

Oh, and do another backup, this last one being perhaps the most important one.
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