The Great iMessage Debacle (Premium)

For the most part, moving between smartphone platforms is a straightforward enough process that I can do so several times each year as needed. But there are some problems that I run into all the time. And the worst of them, by far, is Apple’s fault.

I am referring, of course, to iMessage, a proprietary Apple messaging service and alternative to SMS/MMS text messaging. In the Apple world, iMessage is viewed as a key advantage of the company’s walled garden approach, thanks to its integration across the iPhone, iPad, Apple Watch, and Mac. (“I can send and receive messages on my iPad!”) But to the outside world, iMessage is viewed as a key example of the lock-in that occurs in that walled garden because Apple refuses to let it interoperate with SMS/MMS and the Rich Communication Service (RCS), the modern standard for messaging that’s used by Google, Samsung, and the Android world.

Yes, Apple just revealed that it would finally support RCS on the iPhone, 7 long years after Google adopted it on Android. But not really, right? Apple will treat RCS the same way it treats SMS/MMS in its Messages app, as a green-bubbled second-class citizen. So this “support” is nice, but it will do nothing to eliminate the blue/green bubble divide, a psychological “us vs. them” tactic that Apple uses on its customer base to keep them in line: Blue message bubbles indicate iMessage and are “good” because they are Apple-based, and green message bubbles are from peasants who haven’t yet seen the way. You’re encouraged to bully them into switching to the iPhone, basically.

To me, this green/blue bubble thing is nonsense: As noted, I use the iPhone a lot and I have never once noticed or cared what color the messaging bubbles are when I’m texting. But this is also a real problem and one I’ve experienced first-hand: Both of our kids have nagged my wife to switch to an iPhone so she can be part of the superior blue bubble world. To her credit, she remains unimpressed with their arguments.

But this is also not the iMessage problem of which I speak, it’s just the backdrop for the increasingly strident calls for Apple to be forced to open up this service. As it turns out, iMessage is just one of probably hundreds of micro-strategies that Apple employs to protect and extend its dominance, and when you view it that way, which is the correct way, then you can understand what’s happening in context and compare this behavior to that of, say, Microsoft, a convicted monopolist, or any of the gatekeeper products and services designated by the EU under the DMA: Big Tech forces or coerces their customers who are using a dominant product or service, in this case the iPhone, to use its other products and services. And in doing so, it keeps them on the dominant platform and can artificially—and, as it turns out, illegally—tilt the balance for its other products or services, many of which would never succeed on their own without that leverage. This is Antitrust 101.

Today, iMessage is not designated as a gatekeeper service alongside Apple’s App Store, iOS/iPhone, and Safari. But the European Commission has opened an investigation into the service to determine if Apple’s market power is enough to warrant that designation. Apple does not want that to happen, because it would be forced to make iMessage interoperable with the outside world, eliminating one of those micro-strategies that keep customers locked into its ecosystem and loosening its grip on them in a very tiny way. Apple’s competitors do want that to happen for the same reasons, but they are correct to want that: There is no version of interoperability that is only bad and no version of lock-in that is only good. This is a bizarre place to take a proprietary stand. But you know, Apple.

Anyway, the problem: I switch between Android and the iPhone at least a few times each year. And I just did so when I returned home from Mexico City with my freshly-reviewed iPhone 15 Pro Max, finally got the Pixel 8 Pro I had hoped to receive a month earlier, and then fully transitioned over to the Pixel two days later. And it’s that “fully transitioned” bit that I’m writing about today. Because that transition is difficult when it involves moving from iPhone to Android—the reverse is easier, as is sticking to the same platform—for reasons that are beyond irritating. And the biggest issue is tied to iMessage and is all Apple’s fault.

When you leave the iPhone for Android, you must take certain steps to deregister iMessage from the device’s phone number and SIM card (or eSIM). Ideally, this is done before you leave the iPhone, since there are steps you can proactively take on the iPhone to make this happen. But you can also deregister iMessage after the fact from the Apple website. That’s helpful because Apple of course doesn’t do a thing to warn you about this fact: If you don’t deregister from iMessage, your iPhone-using contacts will continue to message you normally and those messages will either disappear into the ether or they will pop up on some other Apple device—an iPad or Mac, most likely—that you might still use. But they will not be delivered to your new Android phone.

I want to be clear about three things here.

This is a deliberate tactic on Apple’s part to keep people on the iPhone. Instead, of just deregistering you from iMessage when you factory reset the iPhone, or at least giving you that option, Apple simply lets you go forward without even warning you about the implications of not making this hidden settings change. You’re just left to suffer the consequences. (It prompts you to back up to iCloud (if needed), another leveraged Apple service, and informs you only that apps and data, your Apple ID, Find My, Wallet, and eSIMs will be removed from the iPhone.)

Two, it’s not just iMessage: You also have to deregister Facetime. If you don’t, your iPhone-, iPad-, and Mac-using friends could try to make video calls with you with the same results. Here, again, this is something Apple could accommodate during a factory reset.

Three, I know all this. And so every single time I move from the iPhone to Android I proactively deregister iMessage and Facetime on the iPhone before resetting it (or not). And I do so from the Apple website as well. I do both.

But here’s the problem: It’s not that simple. There’s actually a fourth thing you need to know, and this is the bit that I forgot in my recent “full transition” to the Pixel 8 Pro: You also have to deregister iMessage and Facetime from any other Apple devices you use. In my case, that’s one device, my iPad Air. And if you look at the timing of my recent escapades, you may have some understanding of the hilarity that ensued.

On November 10, I transitioned to the Pixel 8 Pro. Three days later, on November 13, I flew to Seattle for Microsoft Ignite. And as you might expect, I started getting text messages from friends there when they saw my posts on social media. The problem is, I only got some of them: My iPhone-using friends sent texts I never received on my Pixel, because they got stuck in the iMessage ether. They were, in fact, delivered to my iPad. Where, on the second day, I suddenly realized what had happened when I saw several notifications on that device. F me.

And it’s not just my friends: My son Mark texted me early last week too. And seeing that, I texted him from the Pixel directly. He received that text, but he couldn’t reply. Because of Apple.

See, that’s the problem that occurs when a dominant company refuses to take the simple step of making a proprietary service interoperable with the outside world: It would be easy to let Messages on the iPhone fall back to SMS/MMS if iMessage fails. But Apple would rather display an error message that causes confusion about the problem, suggesting that it is the customer’s (Mark’s) fault or the fault of the idiot using Android. And I’m sorry, but that’s bullshit. That’s why we have antitrust laws, and it’s why the DMA specifically exists, to prevent exactly this kind of behavior.

My son eventually figured out how to send me an SMS manually from his iPhone. But my mother, who also iMessaged me last week to find out my new address (we just moved) will never figure that out. In fact, she’ll just think I ignored her. This is what Apple wants, folks. It really is.

Anyway, I of course deregistered iMessage and Facetime from the iPad as soon as I saw those Messages notifications. But that didn’t fix the problem: My son’s issues with texting me persisted for days until he figured out how to manually text me. And I still haven’t figured out my mom or those other folks (one of whom is from Europe). And today, I was reminded that this problem still wasn’t fixed: I texted Brad to let him know about a morning commitment at our old apartment complex that would impact the recording of First Ring Daily. Wait for it: Brad has an iPhone.

Which I forgot. And as the minutes ticked by and turned into over an hour without a reply, I became concerned. Brad is very good about that kind of thing. The last time this happened, we were supposed to travel to Africa, and he had a crazy reaction to something and needed surgery. So I got worried. Should I call his wife? His boss?

I called Brad first. And he answered immediately (and was fine). And that’s when it dawned on me: Brad uses an iPhone, we had been texting over iMessage while I was on the iPhone, and now we were locked into that even though I did what you’re supposed to do when you leave the platform. (Or most of it, anyway. Again, this would be so easy for Apple to solve.) He had been replying to me. But because I had deregistered iMessage (and Facetime) on my iPad, those messages were just going to the ether, gone forever. And he didn’t get any error messages, and he tried both iMessage and SMS.

Today, I went through the web-based iMessage deregister process yet again. Did this “fix” my iMessage problem? I have no idea. But I bet if Brad tried to text me today it would fail. I hate this system.

And I cannot stress this enough: That is what Apple wants. The dark side of “ecosystem integration” is lock-in, and Apple, as a dominant gatekeeper, is artificially making the messaging experience on iPhone terrible for its own customers on purpose.

I know. The other smartphone platform maker, Google, is even worse: Its “open” system, Android, offers more freedom in every way imaginable but it comes with its own costs, including to your soul, by actively tracking all of your online behavior so that it can sell that data to advertisers and feed its core business. There are no good choices here. I get that, I do.

But come on. Interoperability at the text message level? This is the dumbest thing I and many others have ever experienced. I am begging the EU to come down on Apple for this and put an end to this petty, customer-antagonistic behavior. This is ridiculous.