Upgrading to Server 5 from Lion server

Those documents are out of date.

(139119)

Alexander Chai wrote:

Oh! Then has anyone tried upgrading directly from Lion Server to El Capitan Server?

I haven't and I suspect many other haven't either due to having done versions in between. However in theory I would expect this to be possible except Apple have had a poor history in terms of how well such upgrades succeed. I personally tend to build a new server from scratch and import/restore the data from the old server. For example in the case of Open Directory you would archive the old server and then restore the archive on the new server, or if your even more paranoid about Apple's capabilities you might export the users and groups and then import them on the new server. This later method requires resetting all the passwords either by hand, or in bulk to the same value, or as I did to use the Passenger utility to import and apply a list of passwords to the imported user accounts.

Services like DHCP and DNS have not changed much and one can use the command line tool serveradmin to export the settings from these services and then import them on the new server. A service like File Sharing is best setup from scratch.

Your best option would be to do a clean installation of El Capitan and Server 5 and then manually transfer any data you actually need. It is a lot of work, but has the added benefit of not keeping around any old cruft and easier troubleshooting in the long run.

Upgrading across 3-4 server/OS versions usually creates a lot of headaches. Some of those may even not happen immediately, but only down the road.

If you do not want to invest the time to do so, then your best bet is to do two upgrades by using an intermediate version first.