MobileMe’s Legacy

This week marks the 10th anniversary of MobileMe,1 Apple’s third attempt at a cloud service designed for consumers.2 The service has a pretty rough reputation, but to understand why, we need to talk about the product itself and what went wrong.

Exchange for the Rest of Us

At WWDC 2008, Phil Schiller showed MobileMe to the world for the first time.

The pitch was rather simple. MobileMe was “Exchange – for the rest of us.”

Apple argued that everyone should have access to Exchange-like features, primarily the pushing of personal data such as emails, contacts and calendars.

As Schiller demonstrated in several different ways in the keynote, MobileMe kept all of this information updated, on all of a user’s devices, in real time. You could create a new calendar entry on your Mac, and by the time you picked up your iPhone, the event would already be there. If you edited a contact’s information on your iPhone, you could sit it down, log into your PC, and that new phone number or email address would be waiting for you in Microsoft Outlook.

In his demo, Schiller even showed calendar invites appearing on the screen while in the iPhone’s calendar application. It really did feel like the future had arrived to iPhone users who were used to syncing this data via a USB cable.

Other Features

MobileMe was more than just emails and other personal data. Apple included the photo gallery feature from .Mac, as explained on the MobileMe product webpage:

When your friends and family visit your MobileMe Gallery, they’re in for a show. Just upload photos from your computer or iPhone to your Gallery, and invite people to visit, download their favorites, and even contribute their own. With beautiful animated views, everyone will see your photos come to life.

Apple pitched them as a great way to share photos with family members and close friends. A user could password-protect a gallery and even accept submissions from other users.

MobileMe also included Back to my Mac, a way to connect to your home or office Mac OS X machine remotely that had been part of .Mac. Additionally, Leopard users could sync Dashboard widgets, Dock items, system preferences, and notes with the new service.

The final part of MobileMe was iDisk. Another holdout from previous iterations of Apple’s cloud services.

iDisk allowed users to store, access and share files online. These files could be shared with other MobileMe users, and the whole thing could be managed from the MobileMe website, or right within Finder.

Today, services like Dropbox make iDisk seem quaint, but in 2008, storing a large number of files in a way that you could access them from any web browser was not a simple thing.

Over time, other features came to MobileMe, including publishing iWeb-created websites, Find my iPhone, new versions of the Mail and Calendar web apps and more.

Native Integration vs. The Web

MobileMe was a web service, but most users interacted with it via the native apps on their Macs, iPhones and PCs, not a web browser. Apple hosted web versions of Mail, Calendars, Contacts, Photos and iDisk online at

These web apps were beautiful and felt like desktop applications, thanks to SproutCore, an open-source JavaScript framework used by Apple on the project.

For instance, a user could drag emails into folder or re-arrange their calendars just like they could in Mail or iCal on Mac OS X. Scrolling long lists was smooth, and searching for content in something like Contacts offered real-time filtering. Scrubbing the cursor across a gallery offered fast thumbnail previews, just like in iPhoto.

As beautiful as they were, these web apps couldn’t compete with services like those from Google. They were far simpler than what other companies were offering.

As is true today, 2008-era Apple was a platform company, not a web company. As such, MobileMe was baked deeply into Mac OS X and iPhone OS. Once signed in, the operating system enabled the features across various applications.

(I chuckled when I noticed Apple put “cloud” in quotes in Leopard’s version of the MobileMe preference pane. In Snow Leopard and Lion, the company used simplified language: “MobileMe is the simple way to keep everything in sync on your Mac, PC, iPhone, and iPod touch.”)


Unlike iCloud, MobileMe was a paid service. It even came in its own retail box in Apple’s retail stores:

(Retail employees were burdened with a goal to “attach” MobileMe to 20 percent of their Mac sales. No one in my Apple Store was happy about that.)

MobileMe cost $99 a year, and came with no ads. It came with 20 GB of online storage for use across all of the various components of the service: Mail, Photos, iDisk and more. Additional storage could be purchased. An extra 20 GB cost $49 a year, while another $99 would add another 40 GB to a user’s account.

Customers of the $149 Family Pack had access to 40 GB of storage.

Apple offered a 60-day free trial to allow potential customers to check out the service and get a feel for what it could do for them.

Users of the .Mac service were moved over to MobileMe, but could keep their email addresses.3 New customers were assigned addresses, however. There’s a whole kbase article devoted to this.

Immediate Reactions

Early reviews of MobileMe were bit of a mixed bag. Over at Macworld, Jeff Carlson took issue with the time it took the Mac to sync new data:

iCal and Address Book records under Leopard are updated every 15 minutes (and therefore are not “pushed” when edited, a clarification Apple made after the launch; Tiger syncs hourly). However, calendar and address book updates sometimes applied regardless of the settings I chose in the MobileMe preference pane: with syncing set to Manual, I still watched MobileMe occasionally reach out for updates on its own, though the behavior was inconsistent.

Elsa Wenzel at CNET ran into several issues:

Unfortunately, we bumped into many frustrations during more than several early days of testing MobileMe. Mail from the Mac we used to set up MobileMe appeared on the iPhone that we synced, but it didn’t show up within the online Mail application. Messages seemed to take longer to send and receive in Windows Live Mail than they did in, which, like other glitches relying upon interoperability and online connectivity, may not be Apple’s fault. Four days after MobileMe launched, a first-generation iPhone spent more than two minutes retrieving e-mail from our new MobileMe in-box, which only held five messages. But the same phone spent a second displaying another e-mail in-box.

Perhaps most damaging was the headline on Walt Mossberg’s review:

Apple’s MobileMe Is Far Too Flawed To Be Reliable

I mean, damn.

These reviews were made worse after MobileMe saw large outages in first few months of service. Apple published a support page about the issues on July 28, 2008: Here is Peter Cohen, writing at Macworld that same week:

Apple’s launch of MobileMe has been quite rocky. At first, many users weren’t able to log in or get content to synchronize at all, for example. Apple ultimately responded by apologizing for the outage and offering MobileMe subscribers a 30-day extension to their membership. “The .Mac to MobileMe transition was a lot rockier than we had hoped,” said an Apple spokesman.

Walt Mossberg addressed the early outages in his aforementioned review. Forgive me for the long block quote, but the whole thing is mind-boggling.

I am not referring to the launch glitches that plagued MobileMe earlier this month, such as servers that couldn’t keep up with the traffic and email outages that, for some users, persist as I write this. Those were bad, but they have eased considerably. Apple already has apologized for them and is giving customers an extra 30 days on their subscriptions to make up for the poor start. The problems I am citing are systemic.


But in my tests, using two Macs, two Dell (DELL) computers and two iPhones, I ran into problem after problem. One big issue is that while changes made on the Web site or the iPhone are instantly pushed to the computers, changes made on computers are only synced every 15 minutes, at best. Apple has admitted that this is a problem, and says it is working on it.

But there’s more. The Web site was sluggish, and occasionally calendar entries wouldn’t load at all. Sometimes, you have to manually refresh the Web pages to see changes made on your devices. And when I tried to open my Web-based file-storage page directly from the MobileMe control panel on Windows, I got an error message on both Dells.

My MobileMe calendar, which originated on a Mac, didn’t flow into the main Outlook calendar, but appeared as a separate calendar in Outlook, which was visible only by changing settings. My address-book groups on the Mac, which are simply distribution lists, didn’t show up as distribution lists in Outlook, but as separate address books, and they also weren’t immediately visible. Apple blames Outlook quirks for these issues, but in my view, it should have overcome them.

Other problems abounded. On one occasion, my synced contacts on the iPhone appeared as names only, without any information. In general, synced contacts on the iPhone loaded slowly.

When my Apple Mail program used rules I had set up to automatically file certain emails into local folders instead of leaving them in the inbox, they simply disappeared from my MobileMe account on the iPhone and the Web site. Avoiding this requires a tedious editing of all your rules.

Twice, MobileMe was unable to sync my bookmarks at all, and when it did, their order was scrambled. When I synced contacts to my iPhone, my custom ringtones for particular contacts were lost and had to be reselected.

There’s not much more I can add to that.

Shifting Sands

To Apple’s credit, the outages and slow sync times that had plagued MobileMe’s launch started to fade over time, but a new problem was on the horizon.

Here’s Shawn Blanc, writing in October 2010:

I am grateful for what MobileMe offers — I use iCal every day and would be pulling my hair out if it weren’t always in sync between my iPhone, iPad, Mac — but I could just as easily get my contacts and calendars synced for free via Google. And that is precisely my point. Apple is letting other cloud services define and strengthen the relationship between our desktops, laptops, and mobiles more than Apple is.

In many ways Dropbox and Google are driving the iOS / OS X relationship more than MobileMe is. While MobileMe is syncing my contacts and calendars, Dropbox is syncing my most-dear files: the projects, articles, and notes I’m interacting with every day. What are and MobileMe for if not for the sharing and syncing of everything between our Macintoshes, iPhones, and iPads in sync?

When MobileMe launched in 2008, Microsoft Exchange really was its most direct competitor, in terms of features. However, Google was steadily improving Gmail, Google Contacts and Google Calendar.

Starting in 2009 or so, it was possible to leave MobileMe behind with a handful of now-defunct applications. By 2010, syncing data from Google directly with iOS and OS X was trivially easy.

In October 2011, just over three years after announcing MobileMe, Apple replaced with a free service: iCloud.

MobileMe’s Legacy

When you think of MobileMe, the word failure probably comes to mind.

Less than a month after launch, Steve Jobs wrote a company-wide email concerning the service:


The launch of MobileMe was not our finest hour. There are several things we could have done better:

– MobileMe was simply not up to Apple’s standards – it clearly needed more time and testing.

– Rather than launch MobileMe as a monolithic service, we could have launched over-the-air syncing with iPhone to begin with, followed by the web applications one by one – Mail first, followed 30 days later (if things went well with Mail) by Calendar, then 30 days later by Contacts.

– It was a mistake to launch MobileMe at the same time as iPhone 3G, iPhone 2.0 software and the App Store. We all had more than enough to do, and MobileMe could have been delayed without consequence.

We are taking many steps to learn from this experience so that we can grow MobileMe into a service that our customers will love. One step that I can share with you today is that the MobileMe team will now report to Eddy Cue, who will lead all of our internet services – iTunes, the App Store and, starting today, MobileMe. Eddy’s new title will be Vice President, Internet Services and he will now report directly to me.

The MobileMe launch clearly demonstrates that we have more to learn about Internet services. And learn we will. The vision of MobileMe is both exciting and ambitious, and we will press on to make it a service we are all proud of by the end of this year.

According to an article for Fortune by Adam Lashinsky, Jobs had addressed MobileMe’s failures with the team directly:

Steve Jobs doesn’t tolerate duds. Shortly after the launch event, he summoned the MobileMe team, gathering them in the Town Hall auditorium in Building 4 of Apple’s campus, the venue the company uses for intimate product unveilings for journalists. According to a participant in the meeting, Jobs walked in, clad in his trademark black mock turtleneck and blue jeans, clasped his hands together, and asked a simple question:

“Can anyone tell me what MobileMe is supposed to do?” Having received a satisfactory answer, he continued, “So why the f— doesn’t it do that?”

Lashinsky went on:

For the next half-hour Jobs berated the group. “You’ve tarnished Apple’s reputation,” he told them. “You should hate each other for having let each other down.” The public humiliation particularly infuriated Jobs. Walt Mossberg, the influential Wall Street Journal gadget columnist, had panned MobileMe. “Mossberg, our friend, is no longer writing good things about us,” Jobs said.

Clearly that headline had grabbed Jobs’ attention. Over the next few years, MobileMe grew more robust, with true push syncing coming to the Mac and wide-spread service outages and sync delays being a thing of the past. However, the service could never outgrow its own reputation.4

During the iCloud introduction, Steve Jobs mentioned MobileMe, saying it wasn’t Apple’s finest hour.

He wasn’t wrong about that.

  1. It’s also the 10th anniversary of the iPhone 3G and the App Store. The first week of July 2008 was very busy in the Apple world. 
  2. Not counting eWorld. 
  3. The Apple ID I use for purchasing is my original .Mac email address! Sadly, I missed the iTools days. 
  4. iCloud suffered from its own issues in its early days as well, mainly around content syncing, but it’s been a long time since I’ve had any iCloud service screw something up in a major way. The old adage of “Apple is bad at services” is more and more an old way of thinking.