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 never did much beyond installing Cydia.

Watusi was great, it let you disable the blue checkmark on Whatsapp. (Since been added as a setting)

I also used a tweak that let me auto-block certain phone prefixes that spammers used. Quite useful.

Was also useful that it allowed you to install multiple copies of an app (such as whatsapp), though no longer a need for that either.

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.

The equalizer is easily 20 years old, and is restricted to presets. Presets! A parametric EQ is the only thing that can make Apple's own Powerbeats Pro sound good. And for several golden years (despite lots of Apple's work against it) we had a really good jailbreak equalizer that worked with Apple Music. Eventually I just gave up on the whole thing. But I remember going out for trail runs with good sounding music without worrying about losing my earbuds.

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.

I just want to be able to run things like yt-dlp on iPhone

The only reason to do this today is to turn your iPhone into a tool for other nefarious purposes or clickbot type farms.