Meet iCloud's great-grandfather: iTools

In the beginning — 1994, to be exact — there was eWorld. It was weird, expensive, and poorly marketed. To no one's surprise, it went away.

Six years later, there was iTools. iTools begat .Mac; .Mac begat MobileMe — and a lot of yelling; MobileMe begat iCloud.

The genealogy is a little sparse on worldly details, I'll admit: eWorld was released at a time when the Mac was sagging, and it used AOL's technology to get off the ground. In contrast, by the time iTools was announced — (at the same keynote as the debut of the Aqua interface at Macworld 2000 —  Apple had some major Internet technologies of its own in play:

  • QuickTime 4 with Internet streaming
  • Mac OS 9 with Sherlock 2 and Internet-ready features like keychains and multiple users
  • was seeing 9.5 million visitors a week
  • Apple's online store was doing $1 billion worth of business a year — with the storefront using the company's WebObjects technology.

Macworld 2000 also marked the introduction of a new tabbed design to Apple's website, making the site easier to use and navigate.

The redesign highlighted three new pillars in Apple's Internet strategy: iReview, iCards, and iTools.


iReview housed reviews and rankings of other websites. Initial reviews were written by Apple employees, and the site launched with 250 published reviews. That number grew slowly, as personal Mac users could append to existing reviews, but not create new ones.

"We're going to do to website reviews," Steve Jobs said, "as Amazon has done for CDs and books."

iReview was pitched as a trusted advisor for people exploring the Internet, but it was short-lived. Apple shuttered the site in February 2001 due to low interest.


Apple also introduced iCards, a section of the company's website where users could go to create and send virtual greeting cards.

Arguably, Apple's cards were better-looking and classier than those offered by other greeting card sites at the time. That likely contributed to iCards's eight-year run — the page was shuttered in 2008 with the release of MobileMe.

Digital cards were nice, but the ability to create fully-custom digital and physical cards (and other stationary) within iPhoto and Aperture — and later, Photos and the now-discontinued Cards for iOS) app — ultimately doomed the website.


While in hindsight, iReview and iCards may not have been long-term winners, the final piece of Apple's 2000-era puzzle built the foundation for Apple's modern Internet applications suite.

During iTools's introduction, Jobs discussed that owning both the client OS and the server-side components allowed Apple to create an "entirely new class of Internet services" exclusively for Mac users, free of charge.

iTools was made up of four "revolutionary" products, as shown on this page from OS X's welcome guide:


Touted as a "breakthrough approach" to protect kids on the Internet, KidSafe wasn't an Internet filter; instead, it was a directory of family-friendly websites.

The former, Jobs said, just couldn't keep up with the rapid growth of the Internet. KidSafe was a whitelist of approved sites, rather than an incomplete filter of material that shouldn't be seen by children. It launched with 50,000 websites its directory, all approved by teachers and librarians.

In August 2001, Apple shuttered KidSafe, pointing parents to other sources help keep their kids safe online. However, OS X's Parental Controls system still allows for a whitelist of sites to be used in order to limit kids' browsing: email

With iTools, users could sign up for email addresses at The Apple-run email service provided users with features like auto-reply and auto-forward.

The original email system didn't have any webmail; users had to configure their email clients to talk to the system over POP. email addresses later became in the MobileMe age, before being replaced with Though you can no longer acquire a new or address, you can spot early iTools users by their aliases, which are still active and useable.


iDisk offered users 20MB (yes, MB!) of Internet storage, hosted on Apple's servers. Instead of fiddling with FTP settings, iDisk was baked into Mac OS 9 — there was an icon for it right on the Desktop.

iDisk worked like a regular folder on the system; dragging files in to or out of iDisk would copy them to or from the server. And files in the Public directory were easily shared with other iTools users.

Starting in July 2000, Apple allowed users to purchase up to 400 extra megabytes at a yearly rate of a $1 per megabyte.

While features like the local syncing of files were a few years away, out of all the Internet technologies introduced during Macworld 2000, iDisk perhaps is the most important historically.

Here's part of Kyle D'Addario's reaction after some hands-on time 16 years ago:

This truly is the next level of drag and drop. Mac Observer staff members tested iDisk yesterday evening by sending Macworld [Expo] related files back and forth to each other. The process of storing files in one Public folder, and having those files accessed and saved by somebody else took less than two minutes. Standard Mac OS copy progress bars keep the user aware of the status of the file. iDisk has brought file sharing to the masses. We have heard for years that operating system designers have wanted to seamlessly integrate the Internet with the desktop environment. Sherlock was the first step in that direction, iDisk has finished the job.

If that sounds familiar, it's because Internet-based file sharing is now ubiquitous — thanks not only to Apple, but to companies like Dropbox and Box as well.


The final piece of the iTools package was HomePage, an online program that let users build custom websites without needing to code. HomePage used iDisk as a shuttle for local content like photo albums, movies and more.

Building out a site was as simple as picking a theme, selecting content from iDisk and hitting the publish button. Even in 2016, creating a website isn't that simple for most people.

iTools' legacy

In addition to all of the tech that iTools presented, it brought to life a new partnership. Apple invested in EarthLink, (opens in new tab) to bring the ISP's service to Mac users in a concise way. However, the technology is the big story here. While iTools was launched at the end of the iOS 9 era, it also made the transition to OS X.

While its easy to focus on the OS X transition when thinking about this timeframe in Apple's history, I believe that the company's Internet strategy was vitally important, as well. Mac OS 9 brought a lot of Internet-based tools to the Mac in a new way, while the hardware made it easier than ever to connect.

Of course, like all things, this strategy changed quickly. In July 2002, the much more modern .Mac replaced iTools, offering IMAP and webmail, additional iDisk space and a much improved HomePage, but those upgrades didn't come without cost: .Mac was $99/year, as was MobileMe in 2008.

While many things from Apple's 2000-era Internet strategy haven't made the journey to the present, much of the core ideals persist. With iCloud, Apple has once again reverted to the free-with-paid-storage-upgrades model. And iCloud offers webmail, cloud storage and deep integration with Apple's operating systems, just like its predecessor introduced 16 years ago.

As for reliability, well... that's another story for another day.

Stephen Hackett is the co-founder of the Relay FM podcast network. He's written about Apple for seven years at 512 Pixels, and has more vintage Macs than family members living in his Memphis, TN home.

  • "As for reliability, well... that's another story for another day." As someone who's been using Apple's online tools since pre-eWorld (AppleLink, etc.) I can say that reliability has always been an issue. Less so now with iCloud but it's still there. Apple needs to put as much effort into back-end reliability as they put into industrial design. Why this has been a sore point for them (if there is any one or a few reasons) would be an interesting piece and I hope Stephen writes it.
  • Back-end reliability has a lot to do with redundancy and Apple is currently working to fix that by building more and more data centers as fast as they can. The iOS (iCloud) user base has simply grown way too fast for them to keep up, especially in the passed couple of years.
  • "Ios9 era"? You mean osx9 era? Sent from the iMore App
  • They mean OS 9 era.
  • Aren't we all iTools? Sent from the iMore App
  • I still miss "classic" Mac OS since it was part of my life since it was called a "system" and was black and white. That aside, this article reminded me of a particular tool; iWeb. The first personal website I ever had, I built entirely with iWeb and was so happy to have my little "Powered By iWeb" button at the bottom of my own .com
    Good times. Sent from the iMore App
  • So that would make AppleLink the great-great-grandfather?
  • I've followed iTools/.Mac/MobileMe/iCloud for many years. I still love my coveted .mac account, and use it as my primary email. I really like they brought back iDisk as iCloud Drive. It's important to have an online repository for your stuff.
  • Apple has been slow to develop many of its programs but loyalty pays off. I have been using Apple products since 1990. There have been some moments that have tried my patience, waiting for a feature set to complete, all in all I look back fondly. I've used eWorld, iTools,.Mac, Mobile Me and iCloud all with pretty good success.
    The last few years have been interesting and frustrating with iCloud development. I think in part there has been a change in file manamgnet strategies being rolled out by Apple. Initially Apple was touting the one folder level approach. During this time I stayed with Dropbox keeping my trusty file hierarchy in tact. I was very glad to see the arrival of iCloud Drive with its iDisk and Dropbox feature set and waited patiently for it to show up in iOS. Now I have fully ported over my files to iCloud Drive, everything is working fine. Same for iPhoto - works great! Apple still has a bit of work to with Preview (iOS)and PDF in iCloud. Managing PDF files in iOS has been tricky. IMore has been a good source for me trying to figure out iCloud Drive and it's various interations over the past year or so. Thanks for the interesting articles. I still use for my email address. Which is quite foreign to many people I come across nowadays. I keep the .mac address as sort of vanity plates for my computer.