Mac OS X Leopard: A perfect 10

Apple's new operating system and its massive new feature set challenge users and developers to explore new and better ways of working

No one is unhappy with Mac OS X Version 10.4, known as Tiger. OS X is not an application platform (I bristle at using the term "operating system" for OS X; I explain why below) that needed repair, speeding up, or exterior renovation. Motivations for major upgrades of competing system software — roll-ups of an unmanageable number of fixes, because the calendar says it's time, or because users are perceived to have version fatigue — don't apply to OS X. Apple wields no whip to force upgrades because Tiger stands no risk of being neglected by Apple or third-party developers as long as Leopard lives. Despite the absence of a stick that drives users into upgrades of competing OSes, or perhaps because of it, Apple enjoys an extraordinary rate of voluntary OS X upgrades among desktop and notebook users. Why? People buy Macs because the platform as a whole is perfect, full stop. Leopard is a rung above perfection. It's taken as rote that the Mac blows away PC users' expectations. Leopard blows away Mac users' expectations, and that's saying a great deal.

[ Leopard was selected to receive an InfoWorld Technology of the Year award. See the slideshow of all the winners in the platforms category. ]

Apple's secret, which is no secret to Mac users, is that major OS X releases deliver tangible value far in excess of their asking price, which in Leopard's case is $129. OS X is, first and foremost, a platform for integrated, user-facing applications. And to a far greater extent than previous releases, OS X Leopard itself exploits the facilities that Apple's developers have used to create the vendor's commercial software. Apple hasn't reserved any of the Mac platform's goodies for itself, and users don't need to wait (or spend) for apps that expose the platform's richness in productive ways.

For example, Screen Sharing is now built into OS X; just open the Finder icon for a remote server and click the Screen Sharing button to grab the remote system's display and, optionally, its mouse and keyboard. Apple built Screen Sharing into iChat, and Back to My Mac uses the .Mac service and Screen Sharing to securely tunnel to files and consoles on Macs behind firewalls. All of Leopard is like that — every Leopard feature, even those that would ordinarily be invisible to all but developers, or reserved for the use of the vendor, is planted throughout OS X in the places you'd put it.

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Freedom in the frameworks
Looking at it from a technical perspective, Leopard's step past perfection lies in its extensive use of the combination of the Mac platform's intrinsic integration and Leopard's delivery of hundreds of additions and enhancements to OS X's frameworks.

Apple supplies a consistent, familiar, and well-documented path for developers to do any given thing. In contrast, an entire industry has sprung up around providing developers with proprietary plugs for the gaps that Microsoft leaves in Windows, often intentionally as an aid to the third-party development community. The completeness of the Mac frameworks leaves no room for a marketplace for Mac developer library enhancements.

What's changed in Leopard is that Apple has invested enormous effort to expose Mac framework enhancements to users through OS X's built-in facilities and applications. Leopard's out-of-the-box experience, which I define as the things that a user can do without spending an extra dollar on software, eclipses Tiger's, and Tiger was no slouch in this regard. In the past, third parties have offered freeware and shareware facilities to extend or even replace Finder, the Mac's answer to Windows' primitive Explorer. That died out with Tiger, and Leopard makes such efforts entirely useless. That is not a bad thing.

Unlike Microsoft, Apple is not afraid to put developers out of a given line of business. Leopard integrates e-mail, browser, calendar, search, preview, dictionary, thesaurus, media player, code-free scripted workflow, accessibility, and almost innumerable top-level bundled apps and capabilities that, in one sense, take out any market for supplanting these things. No matter how well Apple does something, someone has cooked up what it feels is a better, but usually just different, way to do it.

Leopard addresses that. Rather than seeing Leopard as a popping of the balloon for third-party enhancements to the Mac's core user experience, a more accurate way of looking at it is that Apple frees developers from trying to improve on that experience. Third parties can focus on new applications instead. Yet, Apple's 300-plus features are all things that third-party developers have at their disposal without requiring any hacks or workarounds to get at. If this registers somewhere between confusing and unbelievable on your scale, I understand. Apple has always let users and developers make their Macs into anything they like. Leopard moves the line between top-level functionality that can be improved upon and baked-in user-facing capabilities that don't need improvement.

Windows and Leopard don't compare
To the user, Leopard drives like the ultimate and ultimately extensible integrated application suite into which the Macintosh happens to boot. Every application installed to Leopard plugs into and extends the suite. Developers can't help it; merely using the Mac frameworks creates a Mac app, which is distinguished by its integration with and extension of the Mac as a whole.

That is why Leopard fits so poorly in the "operating system" category, but at the same time, I don't blame my colleagues for lingering over comparisons between Vista and Leopard. Journalists and observers have to cubbyhole Leopard somehow because the projection of objectivity demands comparison of like products. I can't do that without a lot of bending and forgiving. Vista and Leopard don't compare, and as this is a focal point of other reviews, I'll take up the comparison by way of explaining why I believe it is erroneous and misleading.

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You can reasonably argue that in the commercial space, Windows is always Windows plus Office, and that the combination exceeds Leopard's core capabilities in many ways. Setting cost aside for now, what Office opens to the user does not improve their productivity when they step outside Office. Indeed, there is an entire industry dedicated to creating desktops that effectively boot into Office and hide Windows entirely because, from the standpoint of IT, giving desktop users the run of Windows adds nothing but trouble. This is the reason behind Vista's failure to thrive: IT doesn't want a pretty Windows; IT wants a thin and invisible one, out of users' reach. Over time, Microsoft has filled out Office to function as a user's sole interface, not only to the system, but to the network and the services wired into it. It usually falls to IT to extend Office's capabilities at the server layer, and at great expense.

As to cost, when tallied frankly, the price of a single commercial Windows desktop in an enterprise is potentially infinite, and it is a continuous and growing expense. It is so burdensome that outsourcing the management of Windows clients is another Microsoft-fed industry.

As much as the idea of a PC booting to Office appeals to IT, the idea of a Mac booting to Office is patently absurd. Even hard-core Windows shops concede that point. Likewise, nobody pays for outsourced management of Mac desktops or servers. OS X takes care of that.

Starting Leopard
Now that you understand how Leopard got its 300-plus features (new frameworks extended to the Mac's out-of-the-box user experience) and where it fits, I can move into the review proper. Here, I do not presume that the reader is familiar with the Mac beyond the groundwork that I have laid above.

There are three ways for users to get the Leopard client: As a single-DVD upgrade for their existing Intel or PowerPC-based Mac, as a set of installable discs placed in the box with Macs that ship with Tiger installed, or preinstalled on a new Mac. OS X installs without requiring registration, activation, or a product key. Because you can run OS X only on a Mac, Apple doesn't consider this necessary.

When installed on a new Mac, Leopard includes a digital media suite called iLife '08, which includes iMovie, Garage Band, iDVD, iWeb, and iPhoto. Discussion of this suite is beyond the mission of this review. These elements are well worth discussing in a commercial context, much more so than the multimedia that's in the box with costly editions of Vista. Rather than taking the space here, I'll address iLife '08 in my Enterprise Mac blog. I will review iWork '08, Apple $79 desktop productivity suite, which includes word processing/layout, spreadsheet, and presentation applications, separately.

Existing users install Leopard by inserting the DVD and double-clicking the Install OS X icon that appears when the disc is inserted. This reboots the Mac from the DVD drive. Unless you've done something really weird with your Mac, the upgrade process migrates your existing user and application settings so that when you reboot after the upgrade, everything works as before, but Leopard comes in.

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One snag that commercial users hit during migration is the deactivation of applications that require license keys or online purchase validation. Such applications will demand registration on their first launch, making it all the more critical that you keep a record of your registration keys.

Following installation, Leopard activates Software Update, a free service that rapidly checks your Mac against available updates. All Apple-branded software is covered by Software Update, so it's important to run it again if you install new software after Leopard is running.

Leopard comes with a short printed manual that walks you through its features. It will strike Mac newcomers as bizarre that this tiny manual actually takes a green user from baffled to productive, and with no condescension, no disarming cuteness, and no intimidation. You get used to that. It's common to all Apple documentation and services.

Spoiling users in productive ways
Leopard is intrinsically integrated from the core to the bundled apps, making Leopard useful straight out of the box, no extra software required. That hasn't been the case to this point. Leopard is the first release of OS X that, if made and sold by a competitor, would bankrupt Apple.

The trouble with 300-plus new features is that even Mac users might fear being knocked off balance, if not buried under an avalanche of newness. (And yes, 300 is a verifiable claim, shy of reality if anything; that figure doesn't include a lot of the new system-level and developer goodies.) Millions of users were just finding their rhythm with Tiger (OS X 10.4). Won't most of this go to waste simply because professional users don't have time to stop working and play with the mountain of toys that Apple put under their trees?

The mind-stretcher with Leopard is that the 300 features actually make OS X simpler. You don't have to pull in pieces from elsewhere and fire up AppleScript to flesh out a maximally productive environment. Leopard users will spend far less time bouncing from app to app, or from one System Preferences (the Mac's Control Panel) pane to another, to wire up their workflows. Insider tips are no longer required. With Leopard, Apple has brought everything to the surface. The beautiful part is that the way Apple put Leopard together, the new features don't carry a learning curve. They just seem to appear when you reach for them.

I worked constantly and deeply with Leopard before slogging through Apple's overwhelming master list of Leopard enhancements to make sure that Apple kept its promises. It did. That tedious work done, I'd rather relate some direct experiences with the features that just appeared when I needed them while I was using Leopard. It is by no means a representative sample or a greatest hits remix. Leopard doesn't lend itself to that. I'll just tell you about some of the things that jumped into my hand when I stretched it out.

No matter how big our displays are, they're never big enough. OS X is so slim and fast that Mac users immediately take up the habit of leaving apps and documents open so that they can easily multitask. I multitask best on the two-headed (dual display) Mac Pro in my lab. But an hour into any work session with that machine, I've managed to fill two displays with deep layers of overlapping windows and begun wishing I had another display, and then another.

Now I have them. Spaces creates a set of virtual desktops, each the size of your entire display, that you can flip into the foreground with one keystroke or one click. You can drag an application from one Space to another by dragging a window into the thumbnail for the destination Space. Apple managed to make cut-and-paste and drag-and-drop operations as easy with Spaces as if they are with one desktop, and actually easier than a two-headed system.

I took an immediate shine to Spaces' ability to open a given application consistently in an assigned space. For example, whenever I launch Xcode, Apple's development tool suite, it launches in a Space of its own. You might create one Space for RSS and IM, another Space for browsers, another for video, and another for Office. It's so easy to create, rearrange, and remove Spaces that it becomes as familiar as using the New item in a File menu. You can also pin applications to the screen so that they are present in all Spaces.

Applications that use Apple's OS X frameworks, as all native Mac GUI apps do, inherit an integrated spell check/correction facility that works the same in all cases. Leopard has added a grammar checker that catches a surprising number of gaffes made even by expert wordsmiths such as myself. All apps with text fields are also wired into an Oxford American Dictionary, updated in Leopard so that it's the sweetest online reference book this side of a forklift; and it's also an offline reference book — always there even when your network is not. Leopard also lets you submit the same query to the Oxford Thesaurus, and you can query Wikipedia from inside the Dictionary. Apple reformats Wikipedia findings to make make them more print-like, and Leopard displays a narrowing list of matching words as you type each letter of the word you're after, even for Wikipedia.

Mail and iCal have evolved, as individuals and as a couple. The face of Leopard's Mail client is familiar to Tiger users, but those on Outlook Express and Thunderbird have some adjustments to make, for the better.

Mail is markedly faster in message searching and filtering. Mail content searches across mailboxes are finished in a very short time, while scanning huge mailboxes by sender's name is almost instantaneous. In Tiger, I set aside a Smart Folder, which is a pseudo-inbox view of mail that's been run through pattern-matching filters, to hold mail from InfoWorld. With Leopard, I was able to make a derivative Smart Folder that catches e-mail from my managers and editors, producing an in-my-face notification rule when new mail arrives.

Mail's new Activity pane constantly displays the real-time status of server connections and message transfers (in both directions) among multiple mail servers in real time. If a server is down or connectivity to it is slow, you'll know it immediately instead of assuming that a message has been sent successfully. You'll not only see connections as they're opened and closed, but also the transfer rate of the message.

I have multiple accounts on seven e-mail servers (my own, InfoWorld's, Google's, and others). That's a lot of cracks to fall through, but now I can watch priority e-mail go out, or fail to do so, and I have a chance to immediately flip to a different server if I need to. I can be on the phone with someone, send them an e-mail, and say "it's in your inbox ... now" with confidence once the message transfer progress bar fills in.

Mail is the only collaboration app that I keep open all the time, and the only one whose notifications I bother with. Leopard Mail has a new RSS pseudo-inbox that keeps up with subscribed RSS feeds. A Subject line search within Mail will pull up matching RSS entries as well, and individual feed entries are displayed in the message view pane, just like e-mail. The ringer is Mail's built-in ability to send new RSS updates to me as e-mail. I actually read blogs now because they're part of my essential e-mail workflow, rather than a separate application and task that demand my attention. It works very well, and the kicker is that Leopard Mail can make new blog entries appear in my real Mail inbox.

Mail's Data Detectors find e-mail addresses, URLs, mailing addresses, telephone numbers, dates, and times of day in message bodies. You can right-click over a detected field to show a street address in Google Maps, update Address Book contacts from a phone number or e-mail address, and create iCal events from meeting times mailed to you. A boon for me, and for a friend who doesn't see so well, is that Data Detectors will also display telephone numbers (such as long conference bridge numbers) in screen-filling type with one click.

With Leopard, Apple turned iCal, its weakest bundled app, into a proper professional calendar and scheduler. iCal can send appointments, reservations, and other events to Address Book contacts and groups via e-mail. iCal sends and consumes events packaged in the same RFC 2445 iCal (no relation) format that's understood by Outlook and all other serious calendar apps. I can e-mail an iCal event to my Nokia E61i or BlackBerry and click to add it to their calendar. Leopard's iCal supports the WebDAV protocol for easy synchronization with Web-based calendars such as Yahoo's and .Mac's.

For me, Leopard iCal's home run is the ability to create a new event by dragging an e-mail message (the sender/subject/date line in Mail's message list) and dropping it in iCal. Instead of copying the e-mail's contents into the item description, iCal constructs a hyperlink that opens the original message in Mail using its unique message ID, not its sender or subject.

Easy connections, swift security
Somebody needed to bring some ingenuity to network, file sharing, and firewall settings, which can tangle up even savvy users. System Preferences now supplies an application-based firewall that lets you specify the applications that are and aren't allowed access to the Internet. Any connection attempt from an application not on your list triggers a notification that gives you a chance to block or allow the request. It's a good idea to add downloaded apps to the deny list until you're certain they only reach out to the Internet when you ask them to. This is smarter than the common port/protocol method. App firewalls stop malware and applications that covertly phone home with your personal info. As a bonus, Apple moved firewall settings to System Preferences' Security pane, where it belongs.

Leopard's System Preferences makes network setup and troubleshooting a breeze. All network interfaces — Ethernet, Wi-Fi, Bluetooth, and FireWire on the MacBook Pro — show their real-time status in plain language, and only the minimum required configuration details are displayed and open to change. An Advanced button brings up the original, expert-level Networking preferences pane. It's quite a contrast. I'm a net-savvy guy, and I appreciate the cleaner, simpler view.

Leopard has condensed a systemwide selection of folders to be shared, and permissions attached, with Mac, Windows, and FTP clients into a single Preferences pane with the same at-a-glance, no-tabs design that Network Preferences uses. In that same pane, with a simple checkbox you can enable and disable the servers built into Leopard, such as the Web, remote login (ssh), and Internet Connection Sharing services that give others remote access to your Mac.

Leopard incorporates signed and sandboxed applications. Code signing verifies the integrity of an application, that it really is from Apple or whomever, and that it hasn't been tampered with. Leopard considers all unsigned downloaded executables as suspect. All unsigned apps require your explicit OK before they're allowed to run the first time, and for downloaded apps Leopard displays an especially stern warning. It remembers some of the Web sites from which the apps are downloaded so that you can click to find an application's origin. Once you OK a new application, you won't be asked to do it again.

Sandboxing restricts potentially vulnerable network services, such as Leopard's Web server, to operating within a safe area that blocks efforts to upgrade privileges or access files outside the realm of your personal Web server's contents. Even if an attacker manages to use a buffer overflow or the like to compromise a Leopard service into running arbitrary code, that code can't run privileged or read or write files outside the sandbox. It's a lightweight alternative to putting each vulnerable application in its own virtual machine. Sandboxing is a rare and extremely valuable feature for client systems.

Parental Controls are new to Leopard, and they're useful for more than just parents. They are a simplified interface to the limits and logging that one would ordinarily use server-issued policies and auditing to apply. Parental Controls restrict and/or log the activities of non-privileged users so that they leave a trail that can be reviewed by an administrator. Parental Controls restrict a users' access to a machine to certain times of day, or kick them off after a set number of hours per day. Web sites and Dictionary searches can be filtered for offensive content. Apple uses heuristics, not a blacklist, to filter objectionable Web sites, and any site can be manually added or removed from the restricted set.

For users that need more watching than blocking, Parental Controls logs application launches, site visits, and instant messaging conversations, and it enables remote monitoring and management, which can include shutting down the user's keyboard and mouse if they're caught messing around.

Big brother? For home users — actual parents — online threats are real enough to justify all means of protection. In a small commercial setting that doesn't justify a server to manage a set of Mac clients, Parental Controls may be advisable for new or suspect employees, and they're essential for kiosks, as well as academic and other shared and public environments.

The best made better
Automator, the zero-code scripted workflow engine, first appeared in Tiger. It lets users do the things that normally must be done in hand-coded script by hooking blocks together, with the blocks being all scriptable Mac applications; that covers nearly all native Mac GUI apps. Leopard greatly extends Automator's reach with variables, loops, and wizards, but the knock-out is UI recording. You can drive an application or set of apps with your mouse and keyboard during an Automator recording session, and then turn those actions into an Automator workflow. By adding variables and setting up loops, you can automate the most intricate procedures, not only without code, but with very little wiring.

Automator workflows work just like scripts because they are, and through the magic of integration, Automator workflows can be triggered by such events as incoming e-mail and the appearance of a new file in a folder. But Leopard adds command-line support to Automator so that non-user-facing processes (background processes) and shell scripts can kick off Automator workflows, even injecting variables. I'm all over that. It bridges the immense gap between the OS X GUI and Unix without exposing you to AppleScript, which is powerful but arcane.

Finder is a great example of integration through Apple's consumption of its own dog food. Remote file servers now appear in Finder's sidebar rather than in a separate Network Neighborhood, making file servers as easy to access as DVD-ROMs and local drives. If a listed server supports remote console access through Leopard screen-sharing or the open VNC protocol, one click gives you access to the display, mouse, and keyboard.

To support Spotlight desktop search, Tiger was equipped with the ability to extract data from a wide range of native and foreign content types, such as XML and HTML files, PDF documents, Word documents, and PowerPoint/Keynote presentations, to populate its search database. Apple used this to create QuickLook, which previews any of Leopard's understood file types with one click, without opening the application that created it or even requiring that the application be present on the computer. For presentations and PDFs, you can page through the entire document in QuickLook, and you can expand any QuickLook preview to fill the screen.

Time Machine provides exceptional automatic, continuous backup of client data, handled in the background. For home and individual professional users, Time Machine backs up to an external hard drive attached via FireWire or USB. In a commercial setting, Time Machine can make use of Xserve, which includes Time Machine Server, to protect groups of Mac clients on a LAN. Time Machine isn't archive-like backup that requires a special app for recovery; you can use Time Machine to recover lost files from any point in your system's history. But for me, Time Machine's greatest value lies in its ability to restore an entire Mac from a Time Machine disk or server backup in one click. You're not just covered for lost files and folders. Because Time Machine can be used to recover a full system, you can use it to clone a machine as well. Even in the worst case, you'll lose a few hours' work.

Leopard is remarkable. It's more and better software than anyone should sell for $129 and more than I can stuff into a story that's already way too long. I'll keep riffing on Leopard in my Enterprise Mac blog, where you'll find my take on other Leopard features as I transcribe my experiences and create new ones. If you feel you've been denied a chance to get your geek on, I am now working on a review of OS X Leopard Server, which will describe the Leopard Unix architecture that exists in identical form in the Leopard client reviewed here.

About 11 years ago, I wrote a column (in another publication) in response to letters I had received that called me to task for hailing the arrival of computers that were performance overkill for the majority of users. I wrote that the reason to look forward to the faster personal computer is that it would have the spare firepower and resources to look after itself, to stay out of the user's way while being a microsecond away from answering any user demand, and to make sure that the user never has to do anything twice. That's Leopard.

Additional resources
Review: Leopard Server: The people's UNIX
Mac OS X v10.5 is true UNIX on the inside, novice admin friendly on the outside, and born for collaboration, with turnkey-simple blog, wiki, IM, and calendar services
A developer's-eye view of Leopard, part I
Xray and Core Animation stand out among Apple's immense bag of new Leopard tricks
A developer's-eye view of Leopard, part II
Leopard's Xcode3.0 integrated development environment and Objective-C 2.0 language help define the Mac platform
A developer's-eye view of Leopard, part III
Cocoa and other sweet object-oriented frameworks magically make all Mac apps part of an integrated suite
A developer's-eye view of Leopard, part IV
64-bit Darwin, Dashcode, Time Machine, and Ruby on Rails call on developers to trade out established skills for new ones
Tom Yager: Enterprise Mac

InfoWorld Scorecard
Compatibility (20.0%)
Features (15.0%)
Security (15.0%)
Management (20.0%)
Ease of use (20.0%)
Value (10.0%)
Overall Score (100%)
Mac OS X 10.5 (Leopard) 10.0 10.0 10.0 10.0 10.0 10.0 10.0
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