Apple’s iMessage platform is great, until you leave

I’ve reviewed hundreds of smartphones over my career, most of which were powered by the various flavors of Android. During that time, I almost always had an iPhone in one pocket and whatever the latest and greatest flagship Android phone was in the other.

In between flashy launches and review cycles, I’d switch my Android SIM back to whatever Google’s latest Nexus/Pixel phone was at the time. I’ve always enjoyed Google’s approach to the Android experience.

I considered myself well versed in the nuances that come with using an Android phone, especially in a house and family that’s heavily invested in the Apple ecosystem.

I’d contemplated fully making the switch to Android over the years, but I’d ultimately talk myself out of it due to, primarily, iMessage and the ease of communicating with friends and family.

Heck, for years, I had an iMessage server running in my basement that allowed me to use Apple’s proprietary messaging platform on Android. I rarely, if ever, touched Google’s Messages app.

However, with the release of iOS 18 and Apple’s adoption of RCS messaging, I found myself being pulled back to Android, and more specifically to Google’s Pixel 9 Pro Fold.

Foldable phones are the only real exciting aspect of the smartphone market right now, and given my inclination for Google’s Pixel hardware and software, it was only a matter of time before I’d have one in my hands.

Old habits die hard, I guess.

So, a little over a month ago I ordered a Pixel 9 Pro Fold and the 45mm Pixel Watch 3 w/LTE and made a full switch from iPhone to Android. It’d been years since I last tried to escape Apple’s iMessage prison, and boy was I in for an adventure.

Leaving iMessage is a process

Before moving my SIM over to the Fold, I went through a slow and methodical process of turning off FaceTime and iMessage on every Apple device linked to my Apple ID. First my Mac, then my iPad, then, finally, my iPhone.

From past experience, the order and amount of time you let Apple’s servers catch up with your account settings can make a big difference in the ease of transition.

After a few hours of iMessage being fully disabled, I switched my SIM over to the Fold and slowly started to message my frequent contacts, letting them know I’d made the switch and that messaging me might be hit or miss for a couple of days.

To my surprise, any individual conversations I had instantly switched over to RCS and there weren’t any major hiccups.

Then the trouble started (and continues)

Group conversations, however, were a totally different story, one of which I still feel the effects of today.

On the iPhone side of things, none of the existing group conversations I was part of recognized that my phone number was no longer linked to iMessage. But instead of stopping those people from messaging in that group, or at the very least alerting them that something was amiss, members could send messages to the group as if nothing had changed. Every participant would still receive messages, but I had no clue anything was going on.

The only way I could figure out how to fix it was for me to recreate the group in Google Messages app and to give it a different group name (using the same name just caused iPhone users to default to the iMessage-based group). That seemed to fix it, or so I thought.

However, over the past 6 weeks, my iPhone-toting family and friends have experienced our group conversations reverting themselves back to iMessage-based threads, where once again I’m in the dark and everyone else is getting messages.

The only way they know is because our green bubble thread turns blue.

So, I have to then create yet another group with a different name in order to once again fix it.

Even though I’m not aware of any individual conversations suffering from a similar issue, my confidence level is low that I’ve received all messages sent to me over the last month. I have no clue how many messages people have sent but I never received since making the switch.

Is iMessage worth the price?

There’s zero reason any messaging platform should have so much control over how you communicate with friends and family, and yet, here we are. Apple has effectively hijacked my phone number, but not across the board – only in some instances, of which have no rhyme or reason and I have zero idea is even occurring.

It’s been so frustrating that if I ever decide to switch back to my iPhone 15 Pro, I’m not convinced I’ll even turn iMessage back on.

Then again, the ease at which iMessage simply works across all of my devices -- Mac, iPad, iPhone, Apple Watch -- is something Google doesn’t even get close to achieving. Sure, I can (and do) use the Google Messages web app, but it’s inconsistent and lacks the seamless integration Apple’s Messages app offers.

I guess that’s the price you have to pay, right? In exchange for a messaging platform that’s deeply integrated across all of your devices (assuming you’re all-in on Apple), you give up the rights to controlling messages sent to your phone number, even after you’ve leave.