From iTools to MobileMe

Sandwiched between the many pieces of iPhone news at Monday's Worldwide Developers Conference keynote came a different sort of announcement. Apple's long-standing .Mac Internet service was rebranded—it's now known as MobileMe. But more important, Apple reinvented the Web-based service, adding push calendar, e-mail, and contacts, as well as upgraded versions of the existing iDisk, Mail, and Web Gallery features.

MobileMe appears to be a significant improvement over .Mac, bringing it firmly into the era of the iPhone. Of course this isn't the first time that Apple has revamped its online offering in the service's long lifetime.

When Steve Jobs introduced the pre-cursor to .Mac at Macworld Expo in 2000, it went by the somewhat more fitting name of "iTools," and that's precisely what it was: a suite of Internet-based tools that served as Apple's tip of the hat to consumers' increasingly important online life.

Remembrance of iTools past

At the time, iTools ran exclusively on Mac OS 9—Mac OS X was shown off for the first time at the very same keynote—and was made up of four components: POP-based e-mail served on the mac.com domain, a simple Web site creation tool called HomePage, a Web-filtering service named KidSafe, and an astounding 20MB of remote storage space on a network volume dubbed an iDisk.

While the roots of .Mac are easily visible even in the original iTools release, it's clear that they are mere shadows of the functionality we use today. For example, unlike its later iterations, the first version of iDisk could only be used when it was remotely mounted—there was no always-on file syncing capability as there is now. Furthermore, the connection would log you out after two minutes of inactivity and would never let you stay connected for more than an hour at a time.

That first version of the iDisk gave users access to five basic folders: Documents, for private file storage; Pictures, for sharing photos via HomePage; Movies, for sharing QuickTime videos via HomePage; Public, for public file sharing; and Sites, where iTools users could create Web sites using the HomePage tool.

HomePage was a web-based tool for creating Web sites hosted on mac.com and selecting from a handful of Apple-created templates that were set up for sharing photos, movies, and files. The tool was expanded in July of 2000, when Apple added more complex design capabilities and additional templates. At that point, the company also began to offer additional iDisk space for a fee: you could chose from 50, 100, 200, or 400 extra megabytes at a yearly rate of a $1 per megabyte.

The original mac.com e-mail accounts were POP-only; while Apple offered automatic configuration for Outlook Express 5 on the Mac, other e-mail clients had to be configured manually. No webmail interface was offered, though you could setup an email forward or auto-reply message from a web-based interface.

KidSafe, the final element of the original iTools release, was an attempt to appeal to Apple's traditionally significant presence in the education market by allowing Mac administrators to install a piece of software that would restrict web browsing to approved websites only. KidSafe took a different tack than most filtering software. Rather than trying to block children from accessing undesirable sites, Apple enlisted a cadre of teachers and librarians to mark those sites which were acceptable for kids to view. Unfortunately, the service never caught on and the rapid proliferation of Web sites quickly made the system difficult to maintain. In August 2001, KidSafe became the first part of iTools to get jettisoned.

iTools also introduced the world to iCards, Apple's electronic greeting card offering. While other elements of the service have changed over the years—as we'll see below—iCards has remained more or less the same... though, alas, the arrival of MobileMe looks like the end for iCards (not to mention Web access to bookmarks, iCards, .Mac slides, and support for Mac OS X 10.3 Panther sync) according to this Apple MobileMe FAQ.

Meet .Mac

The first major overhaul to iTools came in July 2002 at the final Macworld Expo in New York City. Jobs announced that iTools, which at the time boasted 2.4 million users, would be renamed as .Mac. Despite the feature changes that came with the rebranded service, the element of the transition that most focused on was the bottom line: iTools had been free to any Mac user but .Mac subscribers would have to hand over $99.95 a year for the privilege of remaining a member. A family pack, added later on in .Mac's lifetime, would offer more storage and support for up to five users for $179.95.

That said, the rebranded .Mac did also add several new features. For example, the e-mail service added support for the IMAP protocol, Web-based access, and boosted storage space to 15MB; the iDisk storage space was bumped to 100MB and added syncing capabilities; Apple introduced Backup, which allowed users to backup their files to their iDisk; and Apple even bundled a copy of Symantec's Virex anti-virus program (perhaps the last time that the company would even tacitly suggest that the Mac might be exposed to viruses). Furthermore, Jobs touted a pair of features that tied in with the upcoming release of Mac OS X 10.2 Jaguar: the ability to share calendar information with iCal and a feature for turning .Mac photos into screen savers.

Still, it was the $99.95 fee that consumers focused in on. Apple announced a month later that it had 100,000 users, but it was a far cry from the millions that had used the service when it was free. Shortly after that, the company released the first public beta version of iSync, allowing Mac users to synchronize their address books and calendar information to their iPods and some phones, and letting .Mac subscribers synchronize the same data between multiple Macs.

And then the service appeared to drop off the face of the earth. For three years, .Mac languished as other providers like Yahoo and Google began offering more and more Internet services to their users. In March 2004, Google launched its Gmail e-mail service in private beta, offering 1GB of storage for e-mail messages; Yahoo and Hotmail boosted their own capacities in response, but .Mac remained at the same meager 15MB.

It wasn't until 2005 that Apple would make another substantive push for .Mac. In September, Apple drew back the curtain on a number of new features and refinements to the service. Once again, iDisk capacity was bumped—this time to 1GB for individual members and 2GB for families—with the ability to allocate space between file storage and e-mail. (An additional gigabyte of space could be purchased for $49.95 a year, showing how much capacity prices had dropped in the five years since the service's introduction.) A new version of Backup.app let you select specific files to backup and added the ability for incremental backups. And Jobs showed off .Mac Groups, a feature that let users communicate, share schedules, and exchange digital media with a select group of friends.

Living the iLife

In 2006 and 2007 Apple continued its irregular schedule of .Mac updates, often trying to combine updates with the iLife software suite. In early 2006, Apple released the first version its Web site authoring tool, iWeb, which had close ties with .Mac, allowing users to host sites created with iWeb on the service. iWeb largely supplanted .Mac's HomePage tool, though sites created with the software could be hosted on other services besides .Mac. However, certain features were only available to .Mac subscribers, such as the slideshow functionality and web widgets.

Several of the software suite's applications had components that worked with .Mac, such as iPhoto, which allowed you to create a Web Gallery of your photos on .Mac, and which was later integrated with the iPhone as well. iWeb, which supplanted the Web-based HomePage construction tool. While iWeb let you host your Web site on services other than .Mac, certain features were only available using Apple's service.

With the release of iLife '08 in September 2007, Apple introduced the .Mac Web Gallery, which tied into iPhoto, iMovie, and iWeb, allowing iPhoto and iWeb users to quickly and easily publish their photos and movies in a web-based gallery. Concurrently, Apple again upped the storage limit of the iDisk, increasing it to 10GB of space for individuals and 20GB for families and with the option of purchasing an additional 10GB of space for $49.95 a year.

Despite all its upgrades over the years, .Mac has faced stiff competition in the online world. Storage space continues to get cheaper and more capacious and the prevalence of social networking sites that allow free sharing of photos and videos like Flickr, Picasa, YouTube, and Facebook have continued to make .Mac an expensive proposition to many. Apple has tried to increase .Mac's value by integrating it with OS X features, but such attempts have been hit-and-miss, such as the unreliable Back to my Mac feature introduced in Leopard.

Will MobileMe be what .Mac should have been all along? At the WWDC keynote, Steve Jobs admitted that Apple had been working on the service for a long time. "I think we've finally got it right," he concluded. But the real test will come when MobileMe rolls out on July 11th and we find out whether it succeeds where .Mac failed.

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