Upgrading to OS X Lion Server? Not so fast

If you're considering upgrading to OS X Lion Server ($49 from the Mac App Store) you may want to wait a bit. Apple's discussion board is lit up with posts from users that quickly updated from Snow Leopard Server to Lion Server that are now suffering the consequences.

Users are reporting major SMB bugs and crashing in OS X Lion Server which renders it unusable on many networks. This thread in particular appears to be one of the worst. Here's a sampling of issues being reported:

I upgraded to lion server when it was released, since then i have been on the phone to Apple every day since. Have been instructed to restore back to snow leopard and upgrade to lion again, then spent 2 days trying to get mail working properly (mail was coming through a day late) once that was sorted all the services stopped working and this afternoon have been told by another apple engineer to install a fresh copy of Lion again!

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Apple "simplified" server management.  This means that they eliminated most services from the Server Admin tool.  The only way to edit vertain settings (such as VPN) other than via Command Line in Terminal is through the Server (app), which only runs on 10.7 Server/Clients.  Then again, DNS is configured through the Server Admin, not the Server (app).  Anyway, two different places to change settings and one of them doesn't run on older clients.

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Upgrading/migrating mail is not strightforward.  The documentation provided by apple is not 100% accurate.  Read posts about mail server storage location issues in this forum or you'll go crazy.

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Issues I currently have... *Services turning on and off. -iCal -Address Book -iChat -Mail *Web / Wiki - Services practically nonexistent. I have reinstalled 4 times. I'm giving up for now, reverted back to SL Server.

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Do not migrate to lion from a working version of snow leopard. I have reinstalled multiple times, attempted migrations multiple times and run fresh installs multiple times. I finally used my carbon copy cloner version to put everything back. It's working and steady after many late night and Hous of calls to apple tech support.

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started out with missing graphs and status on server, then the mail server failed, then the web server didn't deliver pages... just to mention a view facts among other things.

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It's been a nightmare. The Server tool is unusable. It is buggy as ****. User and Group assignments just up and dissapear. They are still present, but you can't see them from the Server Tool. The only way to manage them is to use the Users and Groups Preference Pane, which is a pain also, but at least it works.

The UI for setting permissions (yes, the standard Command-I interface), is screwed up also. It cannot handle simple tasks whithout failing. You never know what it its going to do. You add a group. But it doesn't take. You add it again. It might work. Hevean forbid you want to add a group, assign it read-write, and then apply to all subfolders. LOOKS like it works, but it doesn't. I confirmed this using the command line tools.

People that I've contacted say that the recently-released OS X Lion Server 10.7.1 update doesn't appear to fix many of the complaints. I also hear that Apple is blaming a lot of the Lion Server problems on third-parties.

Extra caution should be taken before installing a major operating system update on a server. Heed my partner David Morgenstern's warnings about Lion (it has issues with file sharing, NAS, printing, FileVault, to name a few). Take your time on an upgrade of this magnitude and research everything on Apple's official support and discussion pages before taking the leap. Sweat the small stuff.

Obviously there are some happy Lion Server users out there (there has to be), I just thought that it was worth noting that the early adopter tax can be extra steep when servers are involved.

Are you running Snow Leopard or Lion Server?