Migrating from Windows Domain (SBS) to Macs (workstations and servers)

Solution 1:

It seems like exchange is the sticking point here. If they could get their LOB app to work sans-exchange and use the OS X Server mail server instead, suddenly everything gets a lot simpler.

You need to communicate this to your client: that you are willing to support it, it is their decision to make, but that this has the potential to be a very expensive and frustrating venture if they end up unable to eliminate the exchange server. Emphasize that Exchange+Outlook provides additional services beyond a standard e-mail and calendar system that the OS X Server+Mac Office is not at this time able to replicate, namely connectivity to the core software the powers the business.

Therefore, your recommendation is that they proceed slowly at first: invest in exactly 1 mac w/ office at this time and not proceed further unless/until you can complete a successful integration of that mac with their LOB app (ie: get all those word/excel/outlook macros working in the mac version of office). Then, if things don't work well you can at least put bootcamp and windows back on the mac and not be out much.

Solution 2:

The Parallels hypervisor works very much like VMware workstation or VirtualBox. You can run the VM in a window or use coherence mode which makes it look like your apps are running in OSX. Users will still need to authenticate to log into their Mac (if connected to AD) and their VM. As for remote access there is a native remote desktop client on mac that will allow it to connect to a remote windows box but to remote into the Mac itself you will need to enable the native remote access which is essentially VNC or use Apple Remote Desktop which is a paid application. Overall this seems like a waste for the business and you since the apps they need are native to Windows.

Solution 3:

We currently run a mixed windows and Mac OSX environment at the college I sysadmin for, and we're currently thinking about moving away from OSX because of a concern with where Apple are going - while I suspect their tools are still a good fit for a small business, they no longer make the servers and storage boxes for larger business that they used to, which suggests they're trending towards being a tougher environment to support in business.

You'll find that you can create an open directory environment in Mac OSX server, which would be the OSX equivalent of Active Directory, and while its not as mature or feature rich as AD, its adequate for most small or medium business needs to be honest.

You'll find printer support (as you mention it in your comment to SonoIT) is actually very good in Mac OSX - unless they've gone out of their way to buy the kind of cheap rubbish that only works with Windows and even then has a reputation for being a bit dodgy - you know the kind of cheap and nasty printers I'm talking about.

The Mac OSX version of office might run macros that will automate tasks within MS Office, but will not play nicely with plugins designed to extend the Windows version of Office, if that makes sense. This will require a fair amount of testing.

Any LOB application that requires customisation of Outlook, plus an Exchange server (and all the AD baggage that includes) is going to greatly complicate things. You'll probably want to bind the macs to AD (which is perfectly do-able) in order to allow people to login to their mac with their AD credentials.

This will be a lot of work to no great use if you end up having to run a copy of Windows inside a VMWare or Parallels session for each user (or, you could run a terminal server and use the Mac version of the terminal server client) in order for them to actually get any work done.

I like using macs at home use myself, so I sympathise with the business owner wanting the same environment at work that they're used to at home, but I'd ask them to thing about what software they need the business to run, think about the cost, and the prospects of productivity decreasing as complexity (and hence the potential for problems) increases and that they need to run the numbers to see if this really makes sense as a business decision.