Migrating Windows SBS to OS-X Lion

Discussion in 'Mac OS X Server, Xserve, and Networking' started by sirsimon, Aug 14, 2011.

  1. sirsimon macrumors newbie

    Apr 26, 2011
    Portland, OR
    Hello all,

    As the title suggests, I'll soon be migrating a client's mixed Mac/Windows SBS 2003 network to a new OS-X Lion server. I've done plenty of Windows-Windows domain migrations (including Exchange email), but this will be my first foray into the Windows -> Mac networking world.

    I accept that there will not likely be any migration tools built into Lion for things like AD user accounts or even Exchange mailboxes, but I was curious if anyone else who has done a similar migration from a Windows AD+Exchange environment to some flavor of OS-X server might have some tips to prevent any potential pain/issues.

    I have many years of experience managing networks (mostly Windows/Exchange), but also am comfortable with OS-X, UNIX, and Linux.

    Thanks for your advice,

  2. throttlemeister macrumors 6502a

    Mar 31, 2009
    I hope so. I also hope you are comfortable with the command line, cause you will be needing it.

    Any particular reason as to why you want to migrate from Windows/Exchange to OS X? While I no doubt will get a lot of flack for this, Windows/Exchange is far superior and more mature in a business environment compared to OS X. I don't know how large this environment is, but where SBS can be set up properly in just a few hours and barely needing attention after, you are likely to spend days to set up Lion to the point of it being useable, and weeks after tweaking it to get the niggles out.

    As far as I know, there are no migration tools available, so you will have set everything up from scratch. I hope you realize Exchange is a lot more powerful than OS X Mail Server/Calendar Server. This doesn't need to be an issue but can present the users with some unpleasant surprises. Also be aware that there seems to be a security issue with network logins accepting any password (see different thread in this forum), which is something you probably don't want in a business environment.

    If there are no technical reasons why you would specifically need OS X server and can't use Windows/Exchange, I would think long and hard about replacing it. And after thinking about it, I would forget about it as in my opinion, the cost of such a migration is not balanced by the benefits, not by a long shot. If it ain't broken, don't fix it.

    And this is from someone that eats and breaths unix (mostly Solaris and Linux) and gets a rash from having to administer Windows.
  3. pismobrat macrumors regular

    Aug 13, 2007

    I can comment as I have decommisioned a handfull of AD networks to OS XServer. And despite warning the companies that it wasn't a solid business plan, three of five called me six months later and bought new Windows Servers from me to deploy and coexist with the mac's.

    If the network is under 10 workstations and has a limited need for folder redirection and you are content with locking systems down at the local level. Then a Mac Server is fine. Will handle DNS DHCP and mail rather well.

    Exchange to Mac Mail. I've not run accross anything compitant for a migration tool. You could move to a hosted Exchange system......

    Another thing that you need to consider, If the network is predominantly windows - You will loose all of your domain level GPO's. There is NO GPO fuctionality in the mac world. I find this a huge reason NOT to move to a mac server. And even if you are using a older version of Exchange - still miles ahead of the Mail Server App.

    If the server is in good shape, under warranty etc. Leave it as is. If there are a bunch of mac's starting to creep up and you need to manage them like you manage a windows network. Buy a mac server for the macs and have a windows server for the windows clients.

    You can joing a mac server to windows domain so that you can use LDAP to retain domain level AD access.

    Best Wishes. Please post your existing network config if you want to explore the scope of this project in more depth with us online

  4. sirsimon thread starter macrumors newbie

    Apr 26, 2011
    Portland, OR
    Thanks for the replies. The organization making the move is tiny (<15 users), mostly has Macs (and will not buy Windows machines going forward). They have nothing crazy going on as far as GPOs and use Exchange purely to send mail. Even the shared calendaring functionality is beyond them.

    I originally suggested that they go with a new Win server, but they were adamant about wanting to give OS-X server a try. They have had a tendency to be a little experimental with their systems. They even tossed out a ShoreTel VoIP system to go Asterisk. Crazy people, I tell ya. ;)

    It will be an interesting project, and I think they'll be happy - they just want to have their data in a safe place that gets backed up regularly. As long as setting up ACLs for folder permissions is straightforward, it should be fairly simple. Their expectation is that it will be somewhat of an 'adventure'.
  5. throttlemeister macrumors 6502a

    Mar 31, 2009
    In that case, have fun. :) It'll be a good learning experience too.
  6. macsimcon macrumors member

    Dec 3, 2008
    We move users from Windows to OS X Server all the time

    That said, we haven't done any Lion Server migrations yet, because we don't recommend moving to a new OS as soon as it's released.

    It is true that OS X Server doesn't have any migration tools to move from Exchange, nor are there any tools for migrating GPOs from AD.

    However, OS X Server along with Kerio Connect is a terrific solution, and Kerio has a great Exchange migration tool. You can get out from under SBS, while still getting 98% of the Exchange functionality users require.

    You can manage policies for the Macs once they're bound to Open Directory. While not as versatile as GPOs, they're still very handy.

    Finally, if you would rather stick with Windows, there's nothing to stop you from binding the Mac clients to AD. The Macs will abide by many of the policies set by AD, but if you want real granular control over them, you'll need to modify the schema. You can do this on-the-fly with products like Centrify, or you can edit the schema to add the ability to manage Mac-specific functions.

    Anyway, getting off of SBS and moving to Lion Server raises certain questions. Why are you doing it? Savings is certainly a viable justification: SBS 2011 is nearly $1,100, with each CAL costing around $70, and those CALs are recurring costs. For the costs of the CALs for five clients, you could buy Kerio Connect.

    If you're using some Lion-specific features (Profile Manager, for example), then I completely understand the move. But if you're just moving to get to the latest and greatest Mac thing, I would hold off. Let someone else's business be the guinea pig.

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