Four weeks and $3,421.88 into my effort to quit using Apple Inc. products, I felt stuck. Most of my app data failed to transfer to my new, non-Apple gadgets. The same went for 103 gigabytes of messages and file attachments. Apple took 15 days to process my download request for the 92,654 photos I'd stored in its cloud—then returned 92,654 errors. I appeared to be trapped inside the company's walled garden.
For more than a decade, I've been an Apple shareholder's dream. I owned an iPhone, an iPad and a MacBook. I wore AirPods and an Apple Watch and subscribed to Apple TV+ and iCloud. I've sprung for regular hardware upgrades and spent extra on official Apple dongles. I've always admired Apple's industrial design and loved how its devices fit together as seamlessly as Ted Lasso dialogue. I've even saved most of the packaging, because it just looked too exquisite to throw out.
Over the past few years, though, it all started to feel claustrophobic. I was only a little annoyed when Siri crept into my apps and search queries. Only a little frustrated that iMessage didn't allow for modern chatting on non-Apple PCs and phones. Only a little miffed that I couldn't choose Google Maps as my default navigator or set up an Amazon Echo as easily as Apple's own HomePod speaker. But these things began to add up, as did the $120 I was spending every year to store my photos on iCloud.
I also started to notice iOS steering my other decisions, including some big ones. Access to Apple's CarPlay dashboard was a key reason my wife and I bought a Subaru Outback. Ditto our LG television: We wanted a TV that could mirror videos from our iGadgets. I decided against a long series of smaller buys, including Microsoft Surface tablets, Fitbits and Sony headphones, primarily because they didn't integrate as well with Apple gear.
This was Apple's plan. In a 2010 email about mobile-era competition and the coming "Holy War with Google," then-Chief Executive Officer Steve Jobs ordered his lieutenants to "tie all of our products together, so we further lock customers into our ecosystem." (Apple has said this approach is vital for user safety and platform security.) Under Tim Cook, Jobs' successor, Apple has widened its remit into all kinds of accessories (wireless earbuds, customizable watches, magnetic chargers) and subscriptions (for music, games, fitness programs, streaming shows and movies). Last fall, with Apple's Vision Pro headset on the horizon, I decided to try a more flexible digital experience before the company locked up my meta-life, too.
My iPhone and MacBook were nearing the end of their useful life, so my plan was to switch to a mix of software centered around a high-end Android phone and Windows laptop, augmented by goods from Amazon, Garmin, Samsung and whatnot. It sounded straightforward enough. Apple's competitors have had a long time to figure out how to Voltron themselves into something resembling a cohesive package. Still, there was plenty of scoffing when I told people what I was doing—even from the competitors themselves. When I emailed Google to request interviews with executives about the switching process, a spokesperson accidentally copied me on a note to his team in which he mocked the very idea that an Android-and-friends model could work as well as iOS. "It's like doing a car comparison but trying to compare a Honda to a car you build from parts you got at Pep Boys," he wrote.
Apple's market value crossed the $3 trillion mark on the last day of June, amounting to about $1 trillion gained in the first half of the year. As my colleague Mark Gurman noted in a newsletter, while the company reached the $3 trillion threshold not long after the unveiling of the Vision Pro, the achievement represents a bet less on the future of the headset, or Apple's nascent work with the hottest artificial intelligence technologies, than on the company's existing ecosystem. "It becomes very hard for consumers to leave that ecosystem. That's what makes investing in Apple so attractive," Gurman wrote.
Although the US Department of Justice is said to be prepping an antitrust case against Apple, the company looks to be on firmer ground after mostly winning a lengthy court battle against Epic Games Inc. this spring. Epic had accused Apple of monopolistic practices in the management of its App Store, which takes a cut of software purchases and has restricted workarounds that circumvent that cut. "The garden could've had a door," Epic attorney Katherine Forrest argued. "It's artificially walled in." An appeals court ruled that Apple's store policies didn't violate federal antitrust law. However, rivals have continued to complain about the company seemingly preferencing its own products: If it's easier to use Apple Pay and Apple Music on an iPhone than PayPal and Spotify, isn't that inherently unfair?
"You're no longer competing purely on the merit of the product," says Carl Pei, co-founder of Chinese electronics maker OnePlus Technology Co. and the new smartphone startup Nothing Technology Ltd. If a person owns both an iPhone and an Apple Watch, Pei says, the chance of getting them to leave iOS is incredibly low. He adds that the Apple-only iMessage service has become "basic infrastructure" of communication and forces a limit on how much new mobile players can grow without it. A Google spokesperson said in a statement, "We believe it should be easy for users to switch between devices and platforms whenever they choose, and we find it frustrating that these principles are not equally shared by all platforms."
An Apple spokesperson said in a statement that the company has worked to make it easier to transfer data to other services. The spokesperson cited documents and testimony from its trial with Epic suggesting that as many as 26% of iOS users purchasing a new phone in 2020 chose a non-iOS alternative. That 3 in 4 people chose to stay reflects satisfaction, the spokesperson said, not lock-in.
Yet after countless hours of troubleshooting (never mind the jokes about green bubbles), I'm not so sure. Instead of resolving compatibility problems, I found, Apple and Google have effectively outsourced them to customers. In particular, moving files from iOS to Android turned out to be shockingly complicated and expensive, and going the other way isn't much more fun. If you've been living inside the walled garden as long as I have, you may find it tough to escape.
It wasn't always difficult to migrate between computing platforms. During the heyday of the PC, jumping from a Dell or Compaq to a Macintosh, and vice versa, was relatively easy, because users had almost unrestricted access to their own files, most of which could be counted on to work across different brands. Yes, the process could be slow in the years before cloud sharing and streaming media, and software had its limits. (See Microsoft Office before the advent of "compatibility mode.") But transferring your data was still simply a matter of moving it all over via external storage.
That portability largely ended in the mobile era. Apple, Google and a graveyard's worth of other companies restricted access to internal software mechanisms, adopted more unique file types and "sandboxed" apps so each one had its own isolated data. Adopting these measures made their operating systems more secure, but it also meant you couldn't simply drag and drop your iTunes music or photo library from an iPhone to an Android device. For a time starting in 2013, a public how-to guide written by Google's then-executive chairman, Eric Schmidt, offered the best instructions for switching to Android, but that was a low bar. Schmidt's online guide laid out six steps just to import your iOS contacts. Another not-so-automated suggestion: "Download in the Google Play Store all the applications you normally use (for example, Instagram)."
Apple and Google invested resources in making the switch easier—the first app that Apple ever published in Google's store was its 2015 "Move to iOS" app—but the paths remained bumpy. A designer who was working for Google around this time recalls that studies on customer feedback showed ex-iPhone users were frustrated by the process of moving media to Android and confused about leaving iMessage. The worse the first impression was with Google, the more likely people were to give up and switch back. This designer, who, like many insiders interviewed for this story, spoke on the condition of anonymity out of concern for career reprisals, remembers one regretful Android tester saying, "I want my life back."
When I began trying to switch late last year, I decided on a souped-up Dell XPS 13 Plus laptop, which seemed sleeker than my MacBook, and chose the latest Google Pixel phone over similar Samsung and OnePlus models because of rave reviews about its camera rig, which uses artificial intelligence to unblur photos and erase blemishes. A Google sales adviser promised that migrating from my iPhone would be as "easy as you copy paste from your computer." This, surprise, turned out not to be true. My files were buried all over the place, and Google's official iOS-to-Android switching service wasn't much help in retrieving them.
Google first asked me to connect the new Pixel to my old iPhone via a USB-C cable and select data to copy: apps, contacts, photos, videos, audio, calendars, etc. As an Apple addict since the iPod days, I knew this would take a while, but after seven hours of loading, I sensed something was wrong. When it finally completed, only a smattering of photos appeared along with random texts from 2011 to 2013, which soon abruptly disappeared. The 63 compatible apps I preselected to move still needed to be downloaded. My 171 iCloud contacts auto-merged in a mess with every Gmail address archived in my account going back to 2005, including nine ancient versions of myself. Mysteriously, an alarm was set for 9:18 pm.
A Google support agent couldn't figure out the problem and referred me to Apple customer service through a 1-800 number. In the meantime, online troubleshooters suggested I try a do-over after a Pixel factory reset. To speed up the process, it was recommended I make a separate request online to Apple to copy my photos and videos directly to Google's cloud so as not to clog the wired iPhone-to-Pixel process. This extra request did accelerate the second attempt, down to around three hours, because I was only moving old texts and other smaller items, but the handoff failed again. No iMessages transferred this time. The 9:18 alarm, however, returned.
The next day, an AppleCare technician called and, to the company's credit, spent 52 minutes suggesting more detailed fixes. But he also said he couldn't evaluate Google's recommended transfer steps for possible issues, because Apple blocked Android's website internally. Asked why I couldn't simply download all my iCloud data right away, he said data management has become much more complex, comparing my suggestion to stuffing tens of thousands of pieces of paper into a fax machine simultaneously. In the end, his tips didn't solve the issue, and my third transfer attempt yielded similar results after three more hours of processing: very few files and one more alarm set for 9:18.
In automated emails I received over the subsequent two weeks, Apple's support team informed me that my photos and videos couldn't be copied because of unsupported file formats, a transfer "timeout" or other errors. I also realized I would have to manually transfer my saved passwords, two-factor authentication codes and Signal and WhatsApp messages.
An ex-Google cloud executive wasn't surprised by the challenges, suggesting that big tech companies only "begrudgingly" implemented these kinds of data-transfer programs following public pressure. "There's no visibility on progress and no recourse other than to request the data again in the event you get 93,000 errors," the exec says. "The platforms will give you your stuff but make the most minimally acceptable effort to export it in a format that other platforms and applications can potentially understand. It's not their job to ensure a successful sync from iCloud to Google."
Before I started this process last fall, David Myhrer, then an analyst at research company IDC, told me he doesn't believe lock-in matters much, because surveys indicate Apple loyalists generally have higher education and income levels compared with other consumers—and, presumably, the means and savvy to switch ecosystems if they want. "Apple users are not being exploited against their will," said Myhrer, now an independent analyst. And it's possible that my experience was glitchier than average. Google rolled out an update in March aimed at increasing speeds of wired transfers. Samsung Electronics Co. also offers its own Smart Switch app on the Google Play store with mostly five-star reviews. But it's tough to tell which Smart Switch users are transitioning from Apple or just another Android phone, and some reviews mentioning the iPhone are horrendous. "Useless," reads one from April. "Wasted 2 days trying to solve the problem." (A Samsung spokesperson says a recent internal customer survey found 90% satisfaction with the process of switching from iOS.)
A former longtime Apple product manager who worked on data transfers says the underlying problems are flat-out tough to solve. This person says Apple and its rivals prioritize their own systems, but they aren't purposely barring the exits. Jérôme Bédat, founder and CEO of DigiDNA Sarl, a Swiss developer specializing in software that extracts iPhone data to PCs, says an open-source partnership established five years ago among big tech companies to make portability easier has failed to fix the overall problem. In the void, "greedy and sketchy" third-party apps of vague provenance have popped up promising to handle Android and iOS data exports for consumers, Bédat says. "It's extremely concerning."
For a little while, all the effort to switch seemed worth it. I was setting up my Dell XPS when Windows conveniently asked if I wanted to integrate my Android phone for desktop texting and also turn on Amazon.com Inc.'s Alexa. The XPS's touch display and gapless keyboard were slick, and the Pixel's camera and speed were impressive compared with my old iPhone. I was excited to try Xbox cloud gaming (which isn't available in Apple's App Store) on my phone, and Google Drive functioned better on Windows than on my old MacBook. Donnie Oliphant, Dell's senior director for XPS, says Dell views the "open garden" as an advantage. "It's a little riskier, because we can't pull someone in and make it a sticky relationship," he says. "You really have to earn it and win that customer."
But subtle frustrations began piling up. Using iCloud on Windows is janky, and there's no iCloud app for Android. The XPS touchpad didn't feel as smooth as Apple's. While my iPhone-using friends joked (I think?) that I was dead to them, my family was annoyed that it was tougher to share videos with my Pixel. For whatever reason, some of my texts failed to send. Much of this poor usability seemed to be more Apple's fault than Google's, because Apple has resisted adopting a communication protocol that could improve sharing between iOS and Android. The impasse was particularly frustrating because I was still a paying iCloud subscriber whose iMessages were stuck on Apple's servers. On that front, I didn't expect much relief. In September, Cook had said he doesn't "hear our users asking that we put a lot of energy" into getting rid of the class system of blue and green bubbles.
Apple is making itself more interoperable in certain ways. The company recently enabled a limited form of iMessage-esque texting from Windows PCs, and Bloomberg News has reported that Apple is preparing to allow outside app stores on iOS in Europe because of government pressure. When asked how much energy it would take to bring a full version of iMessage to other platforms, Ali Akgun, Microsoft Corp.'s corporate vice president for Windows and devices, says, "I don't personally believe there is a big technical challenge to be overcome." But barring further regulatory intervention, escaping the walled garden with all your data is likely to remain technical, time-consuming or both.
I, for one, failed. Neither I nor the experts I consulted could figure out how to get my photos, texts and other data out of iCloud and convert them to files that could live seamlessly on my Pixel or Dell. Eventually, the hassle seemed like more trouble than it was worth. I didn't want to give up a decade of iMessage memories with friends and family, and I couldn't stand having to log back into my Apple account online every time I wanted to find an old photo. So I returned the Android and PC and instead bought a new iPhone and MacBook Air. Although these devices are as refined and powerful as they've always been, Apple didn't have to make the best products to regain my business. I just wanted my life back.
Disclaimer: This article first appeared on Bloomberg, and is published by special syndication arrangement.