Why I'm Switching from Windows Small Business Server to Leopard Server

About 3 years ago I wrote an article about using Macs in my then-new law office, and about a year later, another article about moving the office to Windows. The reasons for that switch were many, though the primary reason was the lack of an equivalent to Microsoft Exchange on the server side and poor support for Exchange on the client side. There were other issues as well: unreliable hardware (see my first-generation MacBook saga), finicky native VPN access, and the clumsiness of Windows integration in early versions of Parallels and Boot Camp.

That was then, and this is now. The following is the first in a series of articles reflecting my current endeavor to bring my 5-person law firm back from a Windows shop with one Mac to a Mac shop with one (virtual) PC.

New Features in Leopard Server

The biggest change of the last three years - and the main reason I am considering this switch - occurred on the server side with the introduction of Mac OS X 10.5 Leopard Server, which added the one piece that has consistently been missing from the puzzle: calendar sharing.

Sure, Macs could always share their iCal calendars over a local area network or remotely using .mac/MobileMe, but there were significant gaps. For one, those calendars couldn't be shared to Windows or Linux machines, except for a limited viewing ability on a .mac web view. To make matters worse, .mac, at least in the months that I used it, was extremely unreliable, with frequent outages to sync services, which for me was the only reason to have the service.

Leopard server adds a calendar server that works not only with iCal, but with other standards-compliant calendar applications on all major platforms. A Windows or Linux (or Mac) using Mozilla Sunbird or the Lightning plugin to Mozilla Thunderbird email, for example, is a cross-platform product that works perfectly under Leopard Server's calendar server.

Leopard Server also has a very simple VPN server that allows secure remote access by both Mac and Windows users, making it very easy to access all of your network resources wherever you are, regardless of which platform your client computer is running.

SBS 2008 Due Real Soon Now

The server side, however, is just one part of the equation. Currently I use a Dell server running Windows Small Business Server 2003 R2 (what a mouthful), which is due for replacement in about a month by an updated product, SBS 2008. Both versions have the same basic functionality, with the differences pertaining mostly to automation, simplification and security. Just as Leopard Server adds all of the new features and eye-candy of Leopard, so too will SBS 2008 add all of the new features and eye-candy of Windows Vista (resource-heavy Aero is disabled by default).

Three years ago, there was simply no comparison. I needed cross-platform shared calendars, and Tiger Server simply didn't give them to me.

Today, things are much better. Exchange Server, which is included in Windows Small Business Server, is a far more powerful system than Leopard Server's calendar server. Exchange is a full-featured enterprise-level directory-based collaboration system that goes far beyond sharing a user's calendar, giving multiple calendars, email accounts and distribution groups, and a great degree of control over access rights and permissions to its many shared resources.

Ease of Use

I have two calendars on my Exchange folder, one shared, one private, and five users have access to my shared calendar. I can control which users can view, add, edit, or delete entries. There are shared appointments, integrated messaging, and a wealth of other features that I haven't even discovered yet after three years of use. In short, I love Exchange, and while I only use a fraction of its capabilities, it makes my busy schedule and massive email volume manageable.

Leopard Server is not Exchange and cannot match its features. What it can do, however, is make its admittedly lesser feature set more available. Exchange is a complex beast, which explains why I only scratch the surface of its power.

Leopard Server, on the other hand, is very simple, even for non-IT types like me. I cannot have such tightly integrated email, calendar, contact, and to-do features as I do in Exchange, but I will have an easier time managing it and retain enough core functionality to still do what I need to do. iCal is a simple interface for managing the calendar, and with the calendar server, my employees will have the same ability to edit my calendar that they do in Exchange. The mail server at the backend with IMAP accounts and Apple Mail in front accomplish the same for email that iCal and calendar server do for schedules.

So if SBS Server's Exchange is better for email, calendar, contacts, and to-do than Leopard Server, why am I looking to move my business to Leopard Server? Quite simply, for its less-critical, but more complex features - and because my existing server is desperately in need of a resource upgrade, making now the time to look at all options.

SBS has a very powerful VPN server built-in, just like Leopard Server does, but for some reason, while I can get my MacBook to connect and authenticate to the server, I can't get it to access any shared folders or drives. I've pored through technical manuals, blasted away on SBS forums, and even spent the money on a tech support call to Microsoft's server group, yet still I can only access shared volumes outside of my local network when using Windows, be it Parallels, Boot Camp, or on an actual PC.

With Leopard Server, I will gain simple VPN access for my Macs while retaining VPN access for Windows.

Security

Another important consideration for me is security, which means time in the case of a small business without a dedicated IT person. I spend, on average, about two hours per month maintaining my Windows server. That's not too bad, and in typical months when there are no strange events in the log, I find myself content. The trouble starts when there is something in the log, which occurs perhaps every three or four months, or when something just breaks, which has happened three times in the three years I've had the server. In each instance, however, the problem was caused by me when trying to access some feature, like VPN, when I don't fully understand the process.

I'm not an IT guy and don't have or want any Microsoft certifications, so when I buy a new computer, add a new employee, or otherwise have to make a change, I shouldn't be faced with hours upon hours of getting everything to work correctly again.

The only other strange log entries I've seen related to attempts to hack into my system, which I've seen four times in three years, and in all instances, to the best of my knowledge, nobody was able to get in.

I hope Leopard Server will make administering users and remote access simpler, and thus allow me to make fewer of those fun "operator errors" that get non-techies in trouble with Windows servers. Of course, I should also benefit from OS X's lack of malware and increased security, just as I do on Mac OS X clients.

Other Reasons

Another reason for switching is expansion. My current SBS 2003 system has 5 client access licenses (CALs), and that happens to be my current staff. As my firm is growing, I plan on hiring one more person, which with my current system would require the addition of another 5-pack of CALs. (SBS 2008 will have single CALs at $77 each, but that subject will be addressed in my next article.)

Another reason is that I would like to start locally hosting my website, which I currently do not have the expertise to do on SBS 2003. Yes, the tools are all there, but I am just too worried about locking down my Windows server enough to protect my data while opening it up enough to host a website. OS X is a much more secure platform, and I will have much greater peace of mind.

The last reason is just one of simplicity, in that I will only have to deal with one operating system, OS X, for the conceivable future. Sure, I will probably move some of my machines to Snow Leopard when it becomes available, but my guess is that like the move from Tiger to Leopard, there will not be any serious compatibility issues between the two.

In the next installment, I'll compare the costs of upgrading my current Windows server to handle my workload and give some breathing room with the costs of a new Mac Pro preloaded with OS X 10.5 Server.