It’s a mix - for years I wanted root on my iPhones, just like you got on android. In practice, once I had it…? I never did much beyond installing Cydia.

With today’s hardware I might have a different take - the 18 has more than enough hardware to be a laptop so maybe I’d use it for a docking mode. But my gut is I’d probably still want a laptop even then.

To me the upshot is : billions of development, software and hardware, have gone into the platforms - it’s hard to quickly make them significantly better.

When I owned an iPod touch, the advantage of jailbreaking was to give your device certain features that the OS just didn't support. (Hell, I remember early days when iOS didn't even have a concept of wallpaper, the background was just black.)

iOS has come a long way since those days so a lot of the most common use cases of the past are no longer necessary. But the principle is the same - the hardware is a general-purpose computer but the software is locked down unnecessarily in many ways. Jailbreaking lets you do things that are outside of Apple's box.

I jailbroke every iPhone I had for many, many years. Most of the time it was silly skins/tweaks but there were a number of things that were huge QoL improvements. I remember BiteSMS and using it as a way to reply to a text directly in the notification instead of having to leave the app. This was before iOS had that feature and before multitasking, back when if you left the game you were playing the app would quit. Also had folders before stock iOS, things like Control Center, and a whole slew of little tweaks for other apps I used.

The downside to jailbreaking was often the instability but that was also back when the phones were way less powerful. Today, armed with LLMs, I would love to have root on my iPhone again. I'd love to rip out Siri and replace it with Claude Code or something like that.

There's just less reason today for someone like me that liked the utilitarian benefits of a jailbroken iPhone. I used it for gestures, caller mini preview, grouped notifications, etc. All things that are now baked in.