So a couple of Mac consultants walked into one of my customers office and convinced the business owner that they could completely swap in Macs across the board for the entire office.

Being a Mac lover at home (and who isn't?), the business owner jumped at it and now wants to completely migrate everything over.

Losing the customer aside, I think this would be a horrible decision for them because as far as I know, they'd be essentially supporting a Mac and a Windows environment concurrently because their core line-of-business (LOB) applications tightly integrate with Exchange, Office, etc. and while I've tried out Parallels at home on my Mac Book (ran IE, seemed to run ok, but obviously not exhaustive),

I'm failing to grasp how this could make any business sense at all, let alone technical sense, as they would need Windows licensing, SBS Server (for Exchange), CALs, Active Directory (because of the reliance of Exchange), anti-virus (again, because of the Windows OS running in Parallels), and would the Mac guys even be qualified to maintain a Windows environment running side-by-side?

For reasons of due diligence, I'm asking the SF community if there's anything they can share as far as experiences goes, good or bad, and really whether this is at all doable.

Specific questions:

  • Can you natively log into your Windows "VM" desktop with Parallels? Anyone familiar with the underlying hypervisor that Parallels uses?

  • Does Mac support a native Remote Desktop session or would it require VNC Server, etc. to be installed?

I'd like this to be a Community Wiki if the mods feel the same way.


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.

  • The LOB application does not and for the foreseeable future, will not work with anything but Exchange and Office (macros/add-ons for both Word and Outlook) . – gravyface Jan 26 '12 at 17:47
  • Well, you're keeping office, right? Macs will still use Word/Excel/Outlook, etc. It's still just exchange that's the problem. – Joel Coel Jan 26 '12 at 17:50
  • Also- added another sentence to the end of the answer. – Joel Coel Jan 26 '12 at 17:55
  • The LOB applications tightly-integrate with Windows Office (various add-ons and macros for both Word and Outlook); I'm assuming that since these depend on things like Word STARTUP folder and COM add-ins, this would not be available for the Mac flavor of office and therefore, they couldn't use native Office on the Mac. – gravyface Jan 26 '12 at 17:59

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.

  • And because of the dependence on Windows, you'd essentially have twice as many operating systems and their native applications and drivers (printers, my god the printers!) to update and manage. – gravyface Jan 26 '12 at 17:49

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.


Honestly, if they're simply using exchange + office for the majority of what they do... You can get Office for Mac which has the full-blown office suite including Outlook. Additionally, there's also a native Remote-Desktop application for Macs that Microsoft produces.

As long as you don't have specific applications that are built ONLY for Windows-based platforms... there are honestly very-few reasons to use Microsoft Windows over OSX. The only disadvantages I can think of all relate to group-policies & remote management of the workstations. OSX can join a Microsoft domain, and make full use of network shares & such... but completely ignores all the group-policies.

  • They're not. The LOB applications are industry-specific; they would very much be dependent on Windows on the desktop, and the supporting infrastructure of Active Directory, Exchange, etc. At this point, the Macs would be nothing more than expensive hypervisors as really nothing Mac native would be of any practical business use. – gravyface Jan 26 '12 at 17:53

To start there is an RDP client for Mac included in Mac Office, it does work well. And there are alternatives like CORD as well that would not require VNC to be loaded everywhere.

But with your LOB app needing a high level of office integration I would have to say that you would have 2 routes using a VM on your local or Virtualizing the Application (Citrix, ThinApp etc) but that would be just to solve your office related issues with add-ins. I think that virtualizing your app would be harder to setup but much easier to manage and works great on the Mac and even printing is not a problem (screwdrivers is a great solution). This would add administration of the Virtual Apps but lower your time supporting 2 OSs, depends on the situation if this trade off is worth the extra money. I would also say that VMware Fusion is also something to look at the prices are pretty close to Parallels and features they are similar but I would give VMware the upper hand with hardware access via the VM. But I have not used Parallels newest version which I have heard is really good.

The Exchange piece would depend on what version of Exchange you are on this will GREATLY effect the experience you have on a Mac. Exchange 2010 has a much improved client and web interface. And here is where I say BUT there are issues and some issues that require a windows based Outlook client and that starts with Calendaring. If you share calendars or use delegation of calendar tasks some of this can't be done via the web (but via powershell and Windows client) and once it is shared out things are workable. But this is something that if you use it at all in your day it can be pretty frustrating. Plus if there are add-ins for Outlook well there again you are looking at using the client and either a VM or Virtual App solution.

You can make it work but you will have a much more complicated (read as expensive) system than the setup you have now trying to present Windows apps to a Mac desktop. But hey you get to use a Mac at work and at home, I would not mind that at all.

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