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    Sheridan's Avatar
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    Upgrade from 10.6.8 to 10.9

    I'm planning the upgrade of our 10.6.8 server and Mac suite to 10.9. I've done a test upgrade on a Mac client which worked (apart from the ad/od was broken as the server is still 10.6.8)

    I just want to check I'm getting my facts correct here, I'm planning to:

    1) Upgrade the server to 10.9 using the free upgrade from the app store
    2) Purchase the server app (£13.99) and that should then upgrade the server component on the server
    3) Setup the ad/od stuff again on the server
    4) Prepare a client to 10.9, and then use deploystudio to copy it to the others

    Have I missed anything, or totally misjudged the complexity of this?

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    Zoom7000's Avatar
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    I'm not an expert here, and I may be completely wrong, but as far as I'm aware, there was a rather big change from 10.6 to 10.7 server. (Not so much from 10.7 to 10.8 and 10.9) So, an upgrade might break quite a few things. Also, I set up my 10.7 server from scratch and the AD/OD setup was slightly different in that there was a few bits of trust related stuff that you needed to do, but the main principle was still the same. It might be worth trying the setup in a test (virtual) environment before going for broke in the real environment.

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    Sheridan's Avatar
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    I've only done a test upgrade on a client so I'm expecting issues with the server - its just we only have the media for 10.6 and I don't want to buy 10.7 just to skip to 10.9!

    I'll be backing up the server before I try anything!

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    The Server App for Mavericks is simply an App and not an OS as Snow Leopard Server was. This means that '10.9 Server' won't necessarily be upgrading the server components found in 10.6 Server. Everything 10.9 Server needs is contained within the Server app itself. With 10.6 Server important config and data directories were sprayed all over the place most of which were hidden in the UNIX sub-system. When Server App is installed and you run through the setup assistant it will create a Server folder in the top level Library folder and store all the configuration and service directories there instead. Although Apple says migration from Snow Leopard Server to Mavericks is possible the Migration Assistant won't necessarily transfer everything to do with the previous server version in a fit state if at all.

    If it was me and assuming the usual AD-OD integration most educational institutions go for I would export policies for OD Groups and/or OD Computer Groups using WorkGroup Manager first and then start from scratch with the planned server upgrade. Obviously back-up deployment data first plus any important user data that may be on there although I'm not sure why you would have any user data on the Mac server to be honest but you never know?

    Only a suggestion but once you've done the above install Mavericks on an externally attached drive and do a clean/fresh installation. This gives you the added benefit of moving back to 10.6 Server in case things don't work out and if they do you can simply use CarbonCopyCloner to clone the now 'live' and fully operational and tested 10.9 Server to the internal drive and take it from there.

    Antonio Rocco (ACN)
    Last edited by AntonioRocco; 6th May 2014 at 06:55 PM.

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    Sheridan (6th May 2014), Zoom7000 (7th May 2014)

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    Quote Originally Posted by Sheridan View Post
    it's just we only have the media for 10.6 and I don't want to buy 10.7 just to skip to 10.9!
    Download 10.9.2 from the Mac App Store on the Mac running 10.6.8, create a bootable USB flash drive using either DiskMaker X or the createinstallmedia command in Terminal and then do a clean install of Mavericks on the server. That's what we did to start with (since the server we had before was running 10.5 and not integrated with AD and it was easier to start from scratch).
    Last edited by Arthur; 6th May 2014 at 07:33 PM.

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    Sheridan (6th May 2014)

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    Sheridan's Avatar
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    Cheers guys - looks like I've got a few different options to try!

    I'm inclined to export the preferences and then do a fresh install of 10.9, and then re-import the preferences (assuming this is possible between 10.6.8 and 10.9) and then just setup OD/AD again from scratch. I can then sort out the clients.

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    Quote Originally Posted by Sheridan View Post
    Cheers guys - looks like I've got a few different options to try!

    I'm inclined to export the preferences and then do a fresh install of 10.9, and then re-import the preferences (assuming this is possible between 10.6.8 and 10.9) and then just setup OD/AD again from scratch. I can then sort out the clients.
    What services did you have running on 10.6.8 Server? Something in my mind is saying that you can't import preferences, apart from OD policies (I could be completely wrong).

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    Sheridan's Avatar
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    Its only really used for od/ad authentication and preferences, and its also running DeployStudio (net boot etc) and print services.

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    Sheridan's Avatar
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    I'm struggling to get the 10.9 installer, I assume it sticks the file somewhere before the install starts, but I can't find it?

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    Quote Originally Posted by Sheridan View Post
    I'm struggling to get the 10.9 installer, I assume it sticks the file somewhere before the install starts, but I can't find it?
    It should be in the Applications folder. "Install OS X Mavericks" or something similar.

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    Found it! Must have looked there 10 times and missed it! I'm trying Diskmaker X now - seems to take a long time but I'll be patient and see if it creates a USB bootable installer.

    Not having much luck with either DiskMaker or createinstall media - they both seem to get to a point of 'Copying Files', and thats it. The USb drive only shows about 115Mb used and that never changes. Back to the drawing board! Brand new USB pen as well, unless it doesn't like a 32Gb one!
    Last edited by Sheridan; 7th May 2014 at 02:45 PM.

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    Zoom7000's Avatar
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    I've never had issues with DiskMaker X, but it does take an awfully long time of looking like it's not doing anything before it suddenly completes.

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    Hi Sheridan - that's a big jump in OS versions for a server! I can't offer anything better than agreeing with the method AntonioRocco advises. Get yourself a seperate HDD and install Mavericks on it as the target device. The problem from an upgrade is not what happens immediately, but what comes later on down the line.

    My question is: why are you updating to Mavericks? Is it because it's free? Because something in your environment needs it or there is an expectancy to do it?

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    The reason we are moving to Mavericks is because we need various parts of OSX updated to work properly with certain software (music department stuff!) and we can't just update the clients as they use od/ad and preferences dished from the server. The server is only there really for preferences and shared printing so installing from scratch is an option that I might try first. We can't just upgrade to 10.7 as that would involved buying the licenses which isn't possible at the moment.

    I've had to give up on diskmaker and createinstallmedia - neither seems to work. After about 1.5 hours they both have copied 115mb to the flash drive (I've now tried 3 seperate drives) so its going to take about 3 weeks to copy the 5gb image over!

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    Quote Originally Posted by Sheridan View Post
    I'm planning the upgrade of our 10.6.8 server and Mac suite to 10.9. I've done a test upgrade on a Mac client which worked (apart from the ad/od was broken as the server is still 10.6.8)

    I just want to check I'm getting my facts correct here, I'm planning to:

    1) Upgrade the server to 10.9 using the free upgrade from the app store
    2) Purchase the server app (£13.99) and that should then upgrade the server component on the server
    3) Setup the ad/od stuff again on the server
    4) Prepare a client to 10.9, and then use deploystudio to copy it to the others

    Have I missed anything, or totally misjudged the complexity of this?
    I haven't read every post on the thread but I have just done this and set up a brand new network while doing so (Wiped the server and started from scratch) You haven't missed anything off that is just what we did but with fresh OS installs not upgrades. One thing to mention though you may find the update won't download this could be due to how certain county's are setup or there's a cache server somewhere on your LA network. It helps to have a physical copy of Mavericks so you may want to order one!
    Ours works so much better now, a clean version of Mavericks is fast to say the least and after configuring workgroup manager and the rest of the stuff it's ace, I would go as far as saying Macs are easier to manage than Windows machines, although they aren't to fond of proxy servers for some unknown reason!

    If you have any issues you can always PM me I'll try my best to help

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