On my 06 XK, you need two good keys to self program a third. I went to a locksmith for a replacement key and it cost 200.00, but it works.
Well the keys works for Jimmyz, its the remote heads that do NOT work. I'm assuming your key and remote head both work?
My guess, your locksmith got the correct key and correct part number remote head.
Jimmyz got the correct key (which I think the transponder key is the same for all Chrysler Vehicles its the remote head that only work with certain models), but ordered remote heads off the internet assuming any Chrysler Remote head works with any Chrysler vehicle.
The Dealer isn't putting two and two together and realizing that they are being handed the wrong part number remote head for the vehicle, that is why it won't program to the vehicle. They should catch that and tell Jimmyz that is the problem. A lot of Dealers are NOT very competent, so they are just telling Jimmyz, they tried, it didn't work.
BTW, Creek, something to keep in mind. Two ways locksmiths make keys for transponder key vehicles. The easiest way is to use a clonable key and clone the key you give them. The harder, but better way is to use a direct replacement transponder key and Dealer Tools or very expensive locksmith tools to program the vehicle to the new transponder key. If he charged you $200 for a key, I hope he did the more expensive better job and didn't overcharge you for a clone of the key you already have, that many places charge $25-$50.
Here's where it makes a difference. A "Cloned" transponder key replicates the signal of the key it was cloned from. So both keys work with the vehicle because its sees both keys as the same key. But when you go to make more keys using the self-programming feature, it won't work, because you do NOT have two valid keys to initiate the self-programming. When you stick in the first key, then stick in the 2nd key, the car will see it as you just sticking the same key back into the ignition, NOT a 2nd key, even though they are 2 keys, the car sees them as the same key.
That is why its called a clone key. The transponder keys are suppose to be different, every single one, the vehicle is programmed to accept the unique signature of that transponder key as being for it and will allow it to start the vehicle. But they came up a cheap way to make copies and that is to use an aftermarket key that works different and can be programmed to replicate that unique signal from the other transponder key.
The FOBIK's, used in later Commanders, use an RFID chip, that works somewhat like the transponder chip. For some reason, I don't know why, those RFID chips are NOT clonable. So you can't get clones made of those keys, you can only program the car to recognize the RFID chip interaction as being valid for that car.