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HPWC will not latch into charger

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Having trouble with my HPWC/Dual charging 2013 Model S. We've had a cold snap but I'm not sure if that's related (under 32 deg F). I don't ever use anything but the HPWC--if the issue is cold related it would have to be with the onboard inverters or the HPWC nozzle (warning: I am bad with the terminology ;))

Usually after like 10 tries/jiggles it will latch and then charge. I have the issue even after a 45 min commute home so it's likely not the teslas's battery temp.

So far it's been resolveable when I notice it and keep trying to get a connection but this is gonna get old really fast :)
 
My car had this problem for one year before the car port was recently replaced. I thought it was the HPWC until the car port was finally noted to have a crack and replaced. It now works normally again.

Until it was fixed I would need to torque the handle to get a green light. First I would push in, then jiggle, push in harder, then place continuous traction (using the cord looping with just its weight) downward. Over the course of a year this became harder to do. My car is a Signature so I accepted this thinking my HPWC handle was to blame. It is so nice to be able to quickly plug in again. They saw no faults when I reported it earlier and I was expecting to one day replace the handle. This was not replaced and works perfectly again.
 
I've had this same problem with my 2013 S albeit with my UMC as well as several Supercharger cables. I had my warranty service back in December and Tesla replaced both my charge port and my UMC - the problem is worse than ever now. It's definitely much more prevalent as it gets colder, we've had a cold snap recently (-30°C) and my car essentially refuses to connect which is kinda scary.
 
i have a p100d and new wall charger. similar issue.
it will slow charge and say it's not fully in. I can't even push it in, I have to remove it and get a 'running start' smashing it into the car. only then will it work and charge at 48amps.
In my car (not a P100D) there are two clicks before it's fully seated. I push in moderately slow (pushing fast makes them sound as if there is only one click).
 
I had the charger will not latch error and after multiple visual inspections and trying different advice from the forums I blew hard into the car's port and a little piece of plastic came out. That piece was preventing the charger from being fully inserted.

Turns out it was a very small piece broken off my J1772 adapter. Some of these public charging stations have heavy and/or "clunky" handles and I think that trying to get them to fit caused the adapter piece to break off.