Recommended Server Upgrade Procedure

[alembic]

I've got a Mac Mini running 10.8.5 and the appropriate Server version. It's configured as a local sync server for my Contacts, Calendar, Reminders, Notes, etc. My laptops and iPhone sync fine with this setup.

I want to upgrade the Mini to El Capitan now that SMB is fixed(?); but I want to avoid having to reconfigure all the services again. I'm considering:

1) doing a clean install on an external drive, install El Capitan Server app, and then migrate apps and settings from the Mavericks boot drive in the Mini. Once I feel the new OS is working as before, I would then dupe it to the internal drive.

2) backup the internal Mavericks drive, upgrade it to El Captain, and then install Server?

The first option seems less risky but is it doable? The second is probably quicker. Suggestions? Thanks.

 

[jamall]

The other alternative is to create a disk image from your running Mountain Lion Server, install ESXi (either version 5.5 or 6.0 depending on the age of your Mini), restore the ML Server image you just made to a VM and then take as much time as you need to get El Capitan Server running the way you want in another VM. You can then manage the the orderly transition of services over to El Cap one at a time once you've tested the water rather than diving head first into the unknown.

 

[alembic]

Thanks jamall. So I would create VMs for Yosemite and El Capitan and let the server run under the first while configuring the latter. Once I'm satisfied with the functionality of the El Capitan VM, I would "offload" it to the boot drive of the Mac Mini and stop the Yosemite VM?

I'm also unclear about testing the El Capitan VM while the Yosemite VM is operating. If I want to check CalDAV and CardDAV on the El Capitan VM, how do I point client devices like my iPhone to these newly configured services since both VMs would be sharing the same external IP and port number? Or are you saying that I would have to turn off these services on the Yosemite VM before testing them on the El Capitan VM?

 

[sevoneone]

If you are not familiar with ESXi and the world of VMWare, heading down that road in the middle of your upgrade project may not be the best idea.

My suggestion would be similar to your first option: use SuperDuper! Or Carbon Copy Cloner to make a bootable copy of your ML installation to an external drive. Then upgrade the original to El Capitan and the latest version of server and test away. If all is good, awesome. If it starts swimming sideways you have a backup you can easily restore and also boot from to avoid downtime.

 

[alembic]

Sounds good sevoneone. And my apologies for the last post in which I kept referring to Yosemite rather than Mavericks (current Mac Mini OS).