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Which models will be upgraded to the new FSD (as a retro free or otherwise) or can be? I'm looking to purchase off of the inventory listed on the main site, but not sure if its worth buying a 2019 model or if I can purchase a 2018 if the FSD will be available to retrofit later.
 
Hi any model S or X with Autopilot 2.0 should be able to be upgraded to the FSD however if you are buying from inventory it should say if it has enhanced Autopilot and possible FSD. If it’s not listed as FSD call the sales advisor and as to have FSD added on the invoice so you know that 100% when the hardware is released your car will get it as you paid for the option for HW3 hardware 3. Have sent you a PM hope it helps!

Most of not all inventory Tesla’s from 2018 will have AP2.0 hardware
 
Another easy way to check - if there's a picture, look at the Tesla emblem on the side of the car behind the front wheel wells on either side of the vehicle.

AP2 vehicles have a rear facing camera while AP1 and non-AP vehicles have a flat emblem.
 
Another easy way to check - if there's a picture, look at the Tesla emblem on the side of the car behind the front wheel wells on either side of the vehicle.

AP2 vehicles have a rear facing camera while AP1 and non-AP vehicles have a flat emblem.

That’s generally true but there has been at least one report of Tesla replacing the side turn signal on an AP1 car with the new AP2 style camera turn signal (even though the camera is non-functional). Another place to look for cameras is the B-pillars.