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The original was posted on /r/jailbreak by /u/BlackFanDiamond on 2024-07-30 21:20:37+00:00.

I have jailbroken iPod Touches/iPhones since 2009 ish. My favorite memories include jailbreaking Apple store iPhones with jailbreakme website. Jailbreaking my friend’s iPhone with Redsn0w and watching the pineapple load was so much fun. Almost 15 years later, I have transitioned to sideloading for the following reasons.

1. Forced app updates effectively make jailbreaking untenable. The list goes on from banking apps, to Uber, to security apps. I lost it when the Latch app hosting the electronic key for my apartment complex required an update on my jailbroken iOS 14.3 device.
2. iOS 17 and above allow thematic changes that make Winterboard/Snowboard less necessary.
3. Sideloading allows one to access certain jailbroken features for free such as Youtube Ad free.

I made the transition from an iPhone X on iOS 14.3 to a sideloaded iPhone 14 on iOS 17.3. It was the right decision. I hope to inspire others who are on the fence about making the transition.