No doubt that since the release of Snow Leopard a couple weeks ago, you've read a lot about the "Snow Leopard" experience. It's definitely faster, more responsive, and pretty compatible with everything out there, so it seems that Apple has a winner of an OS, especially for the consumers. Good for Apple.

So what about about what's good for us, the professional Mac admins and IT guys who help run businesses that run on Macs? Snow Leopard is great news for consumers, but it's another OS to deploy for us and that's hardly worth jumping up and down for.

What we're interested in is something to make our jobs easier, to simplify our infrastructure, and make our clients or businesses run smoother. That's why we're interested in Snow Leopard Server. Unlike the client, Snow Leopard Server has numerous significant and real improvements - not just to the UI, but also to core functionality. So let's go over it in detail and in depth.

Installation

Installation of OS X Snow Leopard is of course, more complicated than the client version, so please, for those of you untrained in OS X Server installs, don't think that we're saying that anyone can do it. No matter what level of simplicity Apple brings to the UI, a server install will always require planning, forethought, and experience. For those of you who are experienced, you'll find Snow Leopard server one of the easiest installations of OS X Server you've seen. Options for network configuration, services, and directory options are available as they are in the Leopard installation, but are more clearly laid out.

When installing, you'll have the option to activate the basic services (AFP, iCal, iChat server, Address Book server), but the installation doesn't complicate things by allowing you to activate every service (which is a good thing). With the addition of services like Push Notification, Mobile Access, and Address Book server, the list of services available in Snow Leopard server reaches from here to the moon. Snow Leopard, like most of the previous versions of OS X Server, can provide essential network services like DHCP, Firewall, and NAT as well.

Of course, using some of those services requires you to use your server as the core of not only your information services, but also your network. We don't generally recommend that you do that - there's a lot of security and reliability reasons not to put your server with all of your information at the intersection of your public and private networks. However, Snow Leopard is capable of doing such things in a pinch if you need it to.

Missing in Snow Leopard server's installation process is the option to set up a "simple" vs. "advanced" server, a concept brought to us by Leopard server. Unfortunately, it was a process which was a pain in the ass, and I'm glad that it's gone. Snow Leopard Server provides users with a basic administrative utility for the server (Server Preferences) as well as the more advanced version, the Server Admin and Workgroup Manager preferences. No longer do you have to "set" the server to work with one or the other, which is great, as it allows you to have a server be easy to administer for certain more basic functions, but experienced admins can still use the Server Admin.

Interface

Like the client version of Snow Leopard, the usual interface has changed a little bit, but not substantially. You do get all of the advantages of the client OS, with fast updates of file listings and better handling of copied files, faster wireless network reconnections, and smoother notifications of network events. All of these are good things.

In fact, while we were setting up Snow Leopard Server with a few machines in our testing lab, the only major interface difference on the surface was that the Directory Access application is no longer a separate application as part of the Utilities folder. Now located with many similar services in /System/Library/CoreServices, the Directory Access application can now be found under the "Login Options" button of the Accounts System Preference.

A little deeper, we started to find other sensible changes to the interface. One example: assigning permissions for users to have access to services.

In Leopard server, when using iCal server, you would enable iCal services for a user in the "Advanced" tab of Workgroup manager - which was a bit weird, given that other services weren't generally activated on a user by user basis within Workgroup Manager, but rather were under Server Admin's "Access" tab in the server settings.

Adding a user to be an "allowed" user for Address Book Server

Apple obviously looked at this disparity and decided to centralize everything under the "Access" tab in Server Admin, including Address Book Server and iCal Server - which is great. It just took me a little while to figure out where to turn 'on' iCal Server for users, but once I found it, it made sense.

New Services

Once you dive into the Server Administration, then you start to see the new features. First off, the list of services has expanded. New to the list since Leopard Server are: Address Book, Mobile Access, and Push Notification.

Mobile Access and Push Notification are intriguing services, providing better access to services from iPhones and remote users. However, covering those two services alone will require another blog post.

Right now, I'm really interested in Address Book and what, if anything, has changed on the other workgroup services. As one of the few people to have evidently figured out the nooks and crannies of Leopard server's "workgroup" features, I've been wondering if iCal server has improved, if Address Book server works at all, if the Wiki Server does more than it did in Leopard, and if the Mail server is ready for the big time. Let's take them one by one.

iCal Server

As you may have guessed based on my previous posts about iCal Server in Leopard, I have a love of iCal server, because it signifies Apple's realization - about 5 years too late - that OS X server is a lot more useful once it has workgroup collaboration features that can help run a small to medium sized business.

So in my previous post "iCal Server - the Holy Grail Has Arrived" - I had a lot to say about how wonderful Leopard server's iCal server features are. Well, a couple years have passed, and we've all gotten used to this new frontier of having iCal server on OS X Server. Meanwhile, a lot of holes have been poked into the experience, particularly by people who were used to using Microsoft Exchange. Hardly the "Holy Grail," iCal Server became quite a time suck for many OS X Server Admins, and ultimately got implemented only by those willing to put up with its limitations.

One of the biggest complaints had to do with iCal server's inability to invite external users to meetings. While MobileMe and iCal without a server could invite anyone with an email address, iCal Server limited attendees to people within your company. For some people, this wasn't a problem, but for many, this was a deal breaker.

On Snow Leopard Server, that limitation is no more. 10.6 Server brings behind the scenes integration with mail services, so that even if you're not running a mail server on Snow Leopard, you can send out invitations from iCal to external users, who can accept or reject your invitation in their calendar program of choice. There's also a nice checkbox to turn that off if you want.

One other major enhancement is the ability to access Calendars via the web. Strangely, in Leopard Server you could, with some finagling of the Wiki server, view and make changes to a group's calendar, but a user's. While some people created workarounds – syncing their iCal to Google Calendar with BusySync – those were hardly what I would call "business class" solutions.

Finally, with Snow Leopard, Apple's Wiki services include a real web-based calendar which looks to get its UI from the online calendar that's part of MobileMe. It's fully functional and allows users to view, add, move, and delete appointments, even adding attendees to meetings. Finally, calendaring for the Mac has reached some parity with Exchange, at least for what most small to medium sized businesses care about.

Part of the iCal web interface

Installation is also cleaner and simpler, with adding users in iCal becoming a simpler, more guided process than in Leopard Server.

One real limitation remains – and that's how easy it is to manage Delegation in iCal Server. So far, based on our testing, we don't see that the method for delegating calendar access has been simplified. If your company has 10 people and you want everyone to have access to each other's calendars, you have to add users to delegation 90 times (9 users delegated to each of your users). That's hardly a fun prospect for admins of even reasonable sized companies.

Address Book Server

Another deal breaker in Leopard server (for those coming over from Exchange) was the lack of sharable contact lists. Or rather, lack of useable sharable contact lists. The problem was that while Leopard server did technically have a mechanism to share contact information via the LDAP directory, the implementation was... well... very lacking.

In Leopard server, you had to run a separate application (called "Directory") to look up items in the shared contact list, and even when you did so, modifying those contacts was a chore. In fact, the field mappings between Address Book and Directory weren't one to one – so sometimes you'd add data into a contact and it just wouldn't show up in the Directory. It was a great example of something being about 80% baked, but that 20% missing made it effectively useless.

In Snow Leopard, Apple threw that entire system out the door, thankfully. They've implemented a contact sharing system based on the open CardDAV standard, which like CalDAV provides more open sharing of information with a variety of clients (theoritically).

If you're running a Mac, the only client you'll need is Address Book (running in Snow Leopard of course), Apple's standard application. Address Book now has direct access to CardDAV servers, meaning that you can have access to your own local contacts and a Global Address List (to use the Exchange parlance). My, how long it has taken Apple to get serious about collaboration services - but it's good to finally see the results.

Contacts "On My Mac" and On the Server (highlighted)

That means that in a traditional workgroup, users can have their own personal contacts, their own 'shared' contacts on the server, and a company's shared contacts in a generic company account on the server. Most companies won't need much more than that. In fact, that's the Holy Grail of contact sharing for SMBs.

The performance seems fairly good, with 600 contacts going over a LAN in a a minute or so, problem free. No data missing and all fields intact. It's hardly a comprehensive test, but it's a good result out of the box.

For those looking for more high powered collaboration, there are limitations. You don't have the "delegation" capabilities of iCal server or control over 'read/write' vs 'read-only' permissions. So for some high powered execs who have an assistant who needs to manage their contact lists, you can't just delegate control to another account. They'll need to set up multiple accounts in assistant's Address Book including one with the exec's username and password.

For other situations, where you may want a master client list available for employees, but not modified (or worse yet deleted) by them, then Address Book Server isn't quite there yet. Still, I don't anticipate this to be a major roadblock for most organizations, given how little capabilities that we had in the past for sharing contacts (*Cough* MobileMe *Cough*).

Wiki Server

One of the best kept secrets of Leopard server was the built-in Wiki server. While not as full featured as many Web 2.0 applications out there like Basecamp, Leopard server's Wiki server provided simple and powerful tools for sharing content on internet- or intranet-based web pages.

It was very well executed. Adding in-line images, attachments, and tables all worked seamlessly with only a few strange UI peculiarities (mainly with the tables and formatting). It was one of the reasons that we shut down our Basecamp account and started using the Leopard Wikis extensively for Tech Superpowers: unlimited pages and projects on a server which we control. In fact, we put project plans, drafts of reports, tech notes, marketing ideas, and even changelogs on our intranet Leopard server wiki. It's a very powerful structure, perfect for many agile oragnizations.

In Snow Leopard, the same ease of use is there, but Apple has completely redone the permissions and administration of Wikis. In Leopard, in order to create a new Wiki, you had to have access to Workgroup Manager (or the somewhat useless LDAP Directory application), and you had to create a new group just to create a Wiki. No more.

Apple has made the whole process of creating Wikis web-based. Just login as a user, name the Wiki, pick your theme, and set permissions - all on a simple interface accessible with your Open Directory login and a browser. Simple. Best of all, you can have unlimited wikis and pages without getting charged any monthly fees.

Screenshot From Web-Based Wiki Setup

Once a Wiki has been created, the tools are essentially the same as Leopard server: Create or Edit pages; Delete pages (which are still saved for possible recovery by an admin); Add Formatting, Lists, Links, In-Line media (video, audio, graphics, including PDFs), Attachments, and Tables.

The Wiki Formatting Toolbar - Similar to Leopard

Apple's also added the ability to monitor and track changes on multiple Wikis in one place – your "My Page" or "Updates." While it's hard to imagine this page replacing an RSS feeder or your Twitter feed, if your organization has a significant amount of content on OS X's Wikis, I could see this being very handy.

The other huge change is that the themes also support formats with alternate iPhone-friendly layouts, giving iPhone users complete access to the Wiki content and their updates in a nice, fluid interface. While the actual interface for creating and editing pages isn't available on the iPhone, you can view content with incredible ease.

Screenshots from the iPhone Read-Only Interface to Wikis

The bottom line: the Wiki server is an incredibly powerful tool, likely to still be overlooked by many companies - but well worth implementing, even if it's just for the benefit of the IT department.

I've heard of a couple issues of people migrating their Leopard Wikis to Snow Leopard Wikis, but we can't confirm them yet. We haven't made the jump on our production servers (which have 100s of wiki pages), so I'll report back once I know more about the migration process.

Mail Server

Finally, we get to one of OS X Server's most traditional weak spots: Mail services.

What can we say? We don't implement many production servers with OS X Mail Server. Why? Well, the mail database is notoriously unstable. And while more recent updates have helped with stability, the mail service in OS X Server has scared most people away over the years, even in smaller environments.

Leopard server also has pretty piss-poor spam filtering and webmail, with web access to your mail being done through the ancient SquirrelMail php package, which provides a Hotmail experience from c. 2000. It has also been next to impossible to set up server-side vacation messages, which are a feature pretty much built into every Mail server since the dawn of time.

Some of that has changed. OS X Mail is now based on Dovecot, so while the admin pages look very similar, the guts have changed to a hopefully more stable foundation less prone to database and mailbox corruption. In fact, I'm optimistic that this change can bring Snow Leopard's Mail services back up to par with other similar SMB mail services like Kerio and Communigate.

Apple has also added server side mail rules, which allow users to set up vacation messages without *too* much trouble.

What is disheartening is that webmail still sucks. Apple's spent hundreds of hours of dev time on an elegant web-based iCal server interface, Wiki server, and iPhone formatting, but webmail is still stuck in the era of the TCP/IP Control Panel and ResEdit. Want to see how bad the interface is? Just look at Squirrelmail's screenshots. Hardly a business-class solution. "Webmail for Nuts," indeed.

I know that you can add other webmail packages to OS X Server, but I just find it sad that a slick, well marketed, and brilliantly thought-out Server OS like Snow Leopard still has the most basic webmail package ever.

That alone makes me not want to test out the effectiveness of Snow Leopard's spam filters and server side rules. It just seems that the Mail server is being strung along with OS X Server's real features, and that doesn't give me hope that I'll be able to recommend it to my clients any time soon.

Conclusion

With the exception of the Mail Server, Snow Leopard Server is a powerful package. While Apple touted Snow Leopard as a "0 New Features" release on the client side, they snuck in dozens of features into the Server OS: ones which show that they are finally quietly listenting to their business customers.

It's about time.

Still, it's early days – and like with every Server OS, it's never a good idea to install it on your production server in 10.6.0 form. Be cautious, install it on testing systems (I did all of my evaluation of Snow Leopard Server on a MacBook Pro 15"), and get to know it. You'll be happy that you did, because for those of us using all of OS X Server's workgroup features, Snow Leopard would be worth the $999 price tag of previous Server OS's. But at $499 – for the unlimited client license version no less – it's a steal of an upgrade.