Just an update that maybe helpful to the community.
I took the Jeep in to the dealer and we identified the root cause.
In the end, this all came down to the oil change calculation software bug. The first time I was prompted to change my oil (2500 miles) my service advisor tried to talk me out of it. I am used to doing my new cars' first oil change around 3k miles anyway so I went ahead with it. The service advisor told me to ignore the next warning and to come back at 12,500 for my next one.
Fast forward 5 months later, I got my next warning to change my oil and ignored it. A week or so later I refilled my def (was in the red) and a week after that I got a check engine light.
I called my service advisor to schedule an appointment to bring my Jeep in but they were overbooked. Earliest appointment was over a week away, I asked my advisor if he was sure it was ok to drive it in the meantime. He said as long as the check engine light was solid and I didn't see any further issues it was fine.
A couple days later I got the warning that my DPF was almost full and that I should drive at highway speeds for awhile to clear it out. I jumped on the freeway for about 15 miles and couldn't get the regen to start. I then got an "incorrect def" warning. At that point I headed home and planned to take the jeep in first thing in the morning.
This morning I took it in at 7:30am and I got a call at noon that it was ready. All they did was apply the TSB for the oil change bug. That cleared the engine light and they immediately took it for a drive and a regen kicked off almost immediately.
I spoke to the service manager and he believes the check engine light prevented the jeep from going into regen.
1) don't trust your SA when he says to ignore a warning.
2) a check engine light will prevent your jeep from starting a regen, get it looked at.
3) get the oil consumption TSB done
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