I have a Mac Pro (Model Identifier: MacPro5,1) running OS X 10.6.8. The machine serves to the web a couple of MySQL databases (v. 5.0.92) as well as a Redmine installation (with a Subversion repository). Server administration is done using the "Server" application stack (/Applications/Server/Server Admin.app etc.).

I am now considering updating the system to Yosemite (and the new Server.app), but I am hesitating, seeing several reports online about trouble with MySQL installations getting messed up, as well as issues with the Ruby framework. My questions are:

  • Have any of you some experience with updating from 10.6 towards 10.10 in a server setting?
  • Is it more sensible in any way to update in steps, i.e., update to 10.8 first, then to 10.10? If yes, why?
  • What steps need to be taken in order to update the MySQL installation? Again, is it more sensible to upgrade in steps?

EDIT: I have now tried to simply run the upgrade to Yosemite, directly on top of Snow Leopard (obviously, I previously backed up the entire system via Time Machine using an external HD). I then installed the new Server.app application using the App Store. After this, the following problems emerged:

  • MySQL was still in the original location (/usr/local), but could not be run in Terminal, complaining about a missing socket file. Installing more recent binaries of MySQL did not resolve the issue; I will do further research and report again.

  • My Ruby/Redmine installation did not run either. My fear is that I will have to do a complete reinstall of Redmine, since the installation procedure differs from Snow Leopard to Yosemite. Setting up this part of the system was particularly painful (e.g., getting Redmine to communicate with SVN).

Since I need a running system, I downgraded again after this try using my Snow Leopard backup. In sum, I almost tend to not do the upgrade at all, if there is no real pressure from the security side of things.


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