The app is a joke. Once mine expired, I tried to renew online. Nothing but errors. Instead of stating that you cannot renew online because the website hasn't been updated to allow that yet, they just let you error out. I eventually called in to Jeep and the girl informed me that I had to renew over the phone with her until they finish building the payment integration. To my surprise she told me it was $150 a year!! Which is crazy because I have a direct comparison with my 2020 subaru. I paid $75 for THREE YEARS for their app fee and even back then they had vehicle health, reminders, you could customize your climate settings like: driver side temp, passenger side temp, air flow (head/feet/defrost/etc), fan speed, seat heat level, defrost on or off (front and rear). These are super useful for having specific remote start settings for summer, winter, spring/fall.
Basically, Jeep is forcing you to pay a LOT more for far less features than competitors. I brought this up in my conversation and was told "we're working on new features" with no timetable or any information on what those upgrades are.
To make matters even worse, I had to make another service visit to my local dealership for my third software update (not the over the air wifi updates) but a TSB to be able to get additional data on the Jeep app such as tire pressure, fuel level, mileage. You have to call up the service department and then go through the whole story about why you need them to update your brand new Jeep again just to get features you're either already supposed to get in your free trial or that you are now paying for. And hope they know what you're talking about (they usually don't). For reference, you need to ask for TSB 08-174-21 Rev A - Telematics update to get newer features on the Jeep app with a Jeep Connect subscription.