masond

Q: Bringing OSX 10.8.5 and Server 2.2.5 up-to-date

I've been using a mid-2010 Mac Mini as a server, and keeping updates at bay because I just didn't want to mess with it.

 

Now, I've put new RAM in the Mini, and I expect it'll run the current OS and Server.

 

But, before I leap, I thought I'd ask the experts.

 

How complex and time-consuming will an upgrade from OSX 10.8.5 and Server 2.2.5 be?  How many paths will be broken?  How many directories will the upgrade see as obsolete and clean out or delete?

 

Thanks.

Mac mini, OS X Mountain Lion (10.8.5)

Posted on Dec 24, 2015 8:55 AM

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Q: Bringing OSX 10.8.5 and Server 2.2.5 up-to-date

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  • by cdhw,

    cdhw cdhw Dec 24, 2015 9:56 AM in response to masond
    Level 4 (2,653 points)
    Servers Enterprise
    Dec 24, 2015 9:56 AM in response to masond

    In my experience the best strategy is to buy a new disk and do a clean install of OS and Server. Refer to the old version for inspiration when choosing settings but don't let them be set by some migration wizard. Open Directory is a real pig when it comes to not quite working after an upgrade. You're better off assuming it won't work and acting accordingly.

     

    C.

  • by FromOZ,

    FromOZ FromOZ Dec 28, 2015 5:32 AM in response to masond
    Level 3 (545 points)
    Dec 28, 2015 5:32 AM in response to masond

    Having just gone through this whole process (Mavericks + Server 3 to El Capital + Server 5) on a Mac mini I would agree with the other poster. Unless you are into pain and suffering I would not try to upgrade OS X server.

     

    <gripe>

    As much as I like Server.app one has to be realistic — Apple doesn't give it as much love as it should (I read an article where Tim Cook said there are 800 engineers working just on the iPhone/iPad cameras and thought boy you should point some of them at OS X Server) and — and this is more important — it is a bit of a mishmash of Linux/Unix apps with a pretty face but with no straightforward interface to get at settings other than exposed via Server.app and if anything 'precious' breaks then good luck trying to track it down.

    </gripe>

     

    No... I'm afraid you'll have to reconcile yourself to an upgrade.

     

    So, if you have to 'dance with the devil' (not the song) how to do it? Assuming you want/need to keep your old server running during the upgrade, and.... you're not rich and you want to re-use your existing server hardware here's how I did it.

     

    1. I wanted to upgrade my Mac mini by changing the HDD for an SSD. This gives your machine a great performance boost — I got a 500 GB Samsung SSD 850 EVO.  No I don't work for Samsung and don't particularly like them but the drive is great.
    2. I virtualised my existing server basically using the process outlined in this website.

      http://fortysomethinggeek.blogspot.nl/2013/03/convert-physical-mac-into-vm-guest .html

      which I did using Parallels. I did it a little differently to how it is written on the website but essentially the same concept.
      1. Installed Parallels on the Mac mini server (you can just even use the 30 day trial version for this)
      2. Used create virtual machine from OS X recovery partition to create new blank virtual machine — this made the VM exactly the same (OS X version) as the Mac mini server.
      3. Copied the VM file over to another machine (an iMac) with Parallels installed.
      4. Created a second volume on the VM (make it big enough to match the HDD size of your existing server)
      5. Close down all ports on your firewall/gateway device to pause any incoming email etc.
      6. Shut down all services except DNS + DHCP on your OS X Server (and don't make any changes to those running services).
      7. Use Carbon Copy Cloner running on server to make a full sparse image (not folder) backup of your server. I recommend backing up to an external drive attached to the server.
      8. Attach that external drive to the second physical Mac — the one hosting the virtual machine.
      9. Mount the sparse image in the host Mac.
      10. Go into Parallels, boot the VM from the first volume (this is the basic install of OS X which is only there to recover to the second volume).
      11. Inside the VM using Carbon Copy Cloner restore the mounted sparse image to the second volume of the OS X VM.
      12. Inside the VM set the boot volume to the second volume and power down the VM.
      13. In Parallels check/change the VM config to boot from the second volume and make the network bridged not NAT.
    3. Power down the physical OS X server machine.
    4. Power up the VM which should load up the physical-to-virtual (P2V) virtual machine copy of your OS X server and as it is using bridged network the OS X server will appear at its old IP address!
    5. Check the OS X server using usual tools (Server.app either local or network, ping, etc.) when you are happy that it is reachable and functioning with current turned on services (DNS & DHCP) turn on other services — mail etc.
    6. Check other services on local network — send emails etc. If all OK then open firewall ports. Immediately and carefully check services.

    Congratulations — you have virtualised your server.

     

    Why do it this way? Well a) unless you have/want a new physical server the single biggest hassle with in place upgrading is something goes wrong and you rip your hair out trying to find it while your users scream at you because of downtime. If you make a new server with new server host name and/or IP address then you have to touch all client machines. This way you can keep the old server running (virtualised, no-one the wiser) while you take your time rebuilding your existing physical server — you will get an SSD drive won't you

     

    Now the second phase has some points open for discussion but my take on it is that there are enough differences between OS X Server 2/3 to 5 that I say don't bother trying to migrate even data using Migration Assistant. The available documentation I found from Apple didn't inspire confidence. Of course this depends on the extent of what you have setup on your OS X Server — so ultimately it's up to you.

     

    For me it came down to DNS / DHCP / User accounts (Open Directory) / Mail / Time Machine. DNS & DHCP were easy, user accounts I didn't have too many, email I told everyone to make a yearly archive (which they should be doing anyway) and empty out their mailboxes.

     

    Basically when the Mac mini came back with the SSD drive installed I did the following:

     

    1. Clean install of El Capitan with a temporary computer name & IP address. Apply all patches and make sure machine is working.
    2. Pause incoming email by closing ports on the firewall;
    3. Got users to archive their email and checked no email was in anyone's mailboxes on the server.
    4. Power down the VM running old OS X server.
    5. Change networking of VM to disabled.
    6. Change computer name and IP address of new (physical) server to that of the old server. Double check it.
    7. Install Server app.
    8. Double, triple check all networking then following best practices (won't go into here) enable DNS service on server. Assuming that DNS is correct.
    9. Were you using certificates, with Internet legal domain name for internal DNS — have to (re)set that up.
    10. Enable DHCP.
    11. Enable Open Directory and get accounts in (again this is up to you how you do manual or import)
    12. Enable mail — check email sending internally
    13. If all OK then you can open firewall ports.

     

    During all of this you can have the old (virtualised) server running to refer back to — just make sure that the VM network setting is disabled so it cannot clash with new server.

     

    Phew — this got a bit long, sorry. Basically wanted to confirm that it's better to do a clean install and to share how I did it re-using old hardware and while being able to keep the old server running.

     

    Good luck!