By Joe Rosensteel

February 26, 2024 3:55 PM PT

Apple’s mixed-up Messages

Whether it’s attempts to regulate iMessage, or attempts to circumvent Apple’s hardware requirements to use iMessage, there’s sure been a lot of interest in Apple’s meager messaging platform lately. From a competition standpoint, iMessage has a grip in North America, but little penetration elsewhere where more platform agnostic messaging apps are preferred.

What is it that we like so much about iMessage and the Messages app? I use them multiple times a day, across the Mac and iPhone, and yet I’m not sure I would call the experience “good” or advocate for it in any meaningful way that didn’t invoke security and privacy concerns.

Reliability

iMessage delivery has been pretty reliable for many, many years. You send it, a little piece of gray text pops under your message a few seconds later and says, “Delivered” and you don’t have to worry about it.

Sure, there was the weird thing that would happen when you’d try to send someone a photo, but the network connection wasn’t strong enough, and then it would just hang that little blue line, and none of your following messages would get through. You’d have to wait a few minutes until the iMessage failed to send. Surely they’d make that experience better some day, instead of… never improving it?

Then there’s the weird thing that happens when you wake your Mac and it starts notifying you about old messages, and maybe a chunk of message history is missing. Oh well. Sometimes it pops up later.

Occasionally read status gets out of sync, but never anything as bad as Slack, which just celebrated 10 years of not being able to remember what I’ve read.

More often than not I’ve been told that I have Do Not Disturb enabled, when I don’t. Just toggling the little DND in control center resets it, but why does it do that without any rhyme or reason?

There still isn’t an official way to export or archive my iMessage history, which has become something I’m more concerned with these days as I’ve had two occasions, in the past two months, where my iMessage conversation history with my boyfriend of 14+ years temporarily disappeared while I was on cellular, but then just magically popped back when I was on Wi-Fi.

So do I still think of iMessage as reliable, or am I just used to the ways in which it is less than reliable?

Features

I often think that all I really expect out of Messages is the ability to send clear, legible text messages and photos. But even the simplest texts can sometimes trigger message effects that were never my intention. (Congratulations!)

The Apple Cash integration, which highlights every monetary amount with an underline so I always look like I’m trying to ask for money, is especially obnoxious. Clearly someone at Apple who is sweaty for people to use Apple Cash considered it a win-win, but I’m almost never sending money.

As for sharing photos… if I send one photo, it shows up in the original aspect ratio, with some pixels shaved off to round the edges and give it that little message speech bubble tail. If I send two or more photos, then all of a sudden we’ve steered into Whimsical Stack Town where Messages has decided that the clearest way to present the photos I’m sharing is a game of 52 pick-up.

The right thing to do is to tile the photos to fit the space without overlap to maximize the use of our limited screen real estate. I want a contact sheet, not a quirky slideshow. Tapping on the “[X] Photos” to bring up the contact sheet view doesn’t help, because it appears entirely outside of the context of the conversation.

iOS 17 and macOS Sonoma also made it take more effort to share photos via Messages. In iOS 17, everything except audio messages got sucked into the new, terrible, “+” menu. Which is not a menu, but a completely modal screen that obfuscates everything to show you a handful of common message buttons, including Camera and Photos. If you don’t tap the invisible bounds of the thin font used for Camera and Photos, or the small circular icon, you’ll dismiss the dialog entirely.

(Pro tip! In a completely unintuitive and non-obvious stroke of sheer un-genius, you can long-press on the “+” to get to the Photos picker.)

In Sonoma, where even the smallest Mac screen is gigantic, the “+” icon has been replaced with a tiny app store icon button, along with a series of lines as a sort of waveform for the audio message and an emoji icon. Why are the icons different? Who could say?

What I can tell you is that I have to click on the App Store icon, then click the Photos icon, and then wait for that to spawn a floating photo picker panel that is attached to the App Store icon, and can’t be moved or resized. Oftentimes I find it easier to find a photo and copy and paste it into the conversation, which seems more than a little absurd if I stop and think about it.

Fun!

Of course a messaging service, and its apps, need to go beyond the ability to send text and photos. We want to have fun with our conversations. That’s why every chat and messaging app includes the ability to react to messages with fun emoji. Oh, I mean every platform except for Messages, which Jason Snell has been on Apple’s case about for a long time.

The emoji sticker reactions suck. I absolutely loathe the jaunty angle that Messages applies to everything. I didn’t place it at a jaunty angle because I don’t want it to be a haphazardly applied sticker. This isn’t some three-ring binder that I’m trying to jazz up with Lisa Frank stickers.

Apple’s attempt to harness the raw power of fun with the Messages App Store hasn’t died yet, so I guess that still counts as “fun”. It still seems to provide dozens of people with access to official Starbucks Messages stickers.

Probably the most “fun” Messages-only feature is exclusively available to the Apple Watch’s version of Messages, and that’s Fitness notifications. My friends and I use the feature in an almost passive-aggressive way. We send ironic congratulations over short walks, or the baffling “Can I call you later?” prompt. All the other platforms get replies to the fitness notifications, even though the Mac still can’t display the Fitness notification that was replied to! But only the Watch can see the initial Fitness notification to start that conversation.

Pump up the jam

I’m uncertain if Apple’s warmed over iterations of Messages are because they see no reason to really compete in the messaging arena, or if they would be exactly as uninspired if they were regulated out the wazoo. Personally, I would rather see Apple innovate of their own volition to provide us with things like increased reliability and support across their platforms. Give us cleaner interfaces to our most used functions, and fun that feels like actual fun, instead just knocking things slightly askew and telling us they’re fun.

Sent with lasers.

[Joe Rosensteel is a VFX artist and writer based in Los Angeles.]