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Nightmarish Road Trip: LA to Phoenix

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OK, I guess I believe you since you say that's how it happened. It does just surprise me that:
A. You wouldn't notice that your charging handle is clunking against something when it's only halfway in and

B. The car wouldn't be showing any kind of warning light or message when it can't latch. I've had that orange warning light on my port and a reduced rate of 16 amps a couple of times when it is almost but not quite all the way in and can't get that latching pin to go in.

You're misunderstanding what he's saying. You're thinking about the flip side of the problem - when someone else's nubbin is in the supercharger connector, and as a result it can't seat all the way in your car (which still has the guide pins). He's talking about being the poor sap whose guide pin got stuck in some random charging connector - now there's poor contact but a fully latched handle.
 
You're misunderstanding what he's saying. You're thinking about the flip side of the problem - when someone else's nubbin is in the supercharger connector, and as a result it can't seat all the way in your car (which still has the guide pins). He's talking about being the poor sap whose guide pin got stuck in some random charging connector - now there's poor contact but a fully latched handle.
Hmm, I have never heard of the lack of the plastic piece ever causing any issues. I've only heard of it when it is there and just blocks the plug from going in.