Server services won't upgrade successfully

Question

Greetings,
I am attempting to upgrade an intel XServe from 10.5.8 to 10.6. I have attemped a few different processes to achieve a successful result. The issue is that not all the services are upgrading successfully. Initially I cloned the 10.5 system to the 2nd internal drive and attempted an upgrade -- failed. Secondly I attempted a clean install and migration from the 1st drive and again attempted migration from a time machine backup -- failed and failed. In each instance the iChat service and Web services failed to upgrade and only a limited number of groups and users were migrated (the system has 77 users and 21 groups in addition to the built-ins). The system contains 2 dual-core processors, 4gb memory, 2 internal drives and a fibre channel card to an XServe RAID.
Any suggestions?

Answer 1

I have never had success upgrading a server. There are just enough changes with each version that it usually ends up not working or hobbled by some mysterious corruption. Really the surest and most reliable solution is to do a manual setup and importation. Not a pleasant prospect in the short run, but the best bet for happiness in the long haul.
Export the users, groups, and computer groups from the Workgroup Manager (not computers unless you do not bind them to the domain), exporting the settings of your server in Server Admin (File->Export->Service Settings) as references only (consider screen shots if you prefer)!  Set up the new server from scratch, adding each service manually as needed matching the settings from the 10.5 server as appropriate.
Set up all your shares again, etc so they are identical to the way they were in the old server.
In Workgroup Manager import the users, then groups, computers (if you don't bind them to the domain) and computer groups.
Since this process does not include user passwords, you will need to select all users (except the diradmin) and enter a default password. Then require a password change at next login under Advanced->Options... in Workgroup manager. If you are not using OpenDirectory, then I cannot speak to user password management issues.