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240v Extension Cord Question

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It does until the day it doesn't. Plenty of people have been surprised when their car suddently decides to NOT follow the amperage that had been previously set. It's fine for casual use, but to depend on it to keep your house safe day in and out....no way.
In a situation where you’re charging with a 50 amp extension cord and connector with an adapter to a 30 amp circuit on a 30 amp breaker (30 amp breaker being key) then I wouldn’t worry because worst case you’re tripping the breaker and not causing a fire.

On the other hand, 30 amp rated extension cord with 50 amp adapter on a 50 amp breaker is certainly dangerous because you’re relying on software from overloading that extension cord.
 
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Personally for my setup I went with the Tesla mobile connector, plus

Nema Gen 2, 14-30 adapter (for 30amp when the included 20ft is enough)
Nema gen 2, 14-50 adapter (for 50amp when the included 20ft is enough)

30ft 14-50 extension cable (for when I need extra length)
14-50F to 14-30M adapter ( for when I need the extra length but only have a 30 amp plug available)
14-50f to TT-30M (for certain campgrounds)

This setup allows me to charge at 30A and 50A at either 20ft or up to 50ft with only one extension cord. But it does mean that I have to be mindful to always check the amp setting before plugging in, as it’s possible to overdraw when I’m using the extension cord and adapter

One could argue that it’s silly to have this setup since even with the mobile connector with 14-50 adapter and 50 amps available, my model 3 will only charge at 32 Amps but in certain cases those extra 8 amps are worth it.

Im also looking at getting a corded mobile connector (hardwired 14-50 plug) which can handle the full 40amps, which would allow me to fully utilize the 14-50 “ecosystem” I built out

I would use the corded mobile connector at home as well since my area doesn’t have any rebates for EV chargers and I can easily get my electrician friend to wire in a 14-50 outlet!
 
Personally for my setup I went with the Tesla mobile connector, plus

Nema Gen 2, 14-30 adapter (for 30amp when the included 20ft is enough)
Nema gen 2, 14-50 adapter (for 50amp when the included 20ft is enough)

30ft 14-50 extension cable (for when I need extra length)
14-50F to 14-30M adapter ( for when I need the extra length but only have a 30 amp plug available)
14-50f to TT-30M (for certain campgrounds)

This setup allows me to charge at 30A and 50A at either 20ft or up to 50ft with only one extension cord. But it does mean that I have to be mindful to always check the amp setting before plugging in, as it’s possible to overdraw when I’m using the extension cord and adapter

One could argue that it’s silly to have this setup since even with the mobile connector with 14-50 adapter and 50 amps available, my model 3 will only charge at 32 Amps but in certain cases those extra 8 amps are worth it.

Im also looking at getting a corded mobile connector (hardwired 14-50 plug) which can handle the full 40amps, which would allow me to fully utilize the 14-50 “ecosystem” I built out

I would use the corded mobile connector at home as well since my area doesn’t have any rebates for EV chargers and I can easily get my electrician friend to wire in a 14-50 outlet!
A caveat about using the 14-50 at 40 A: Many "14-50" outlets actually only have a 40 A circuit breaker, especially in Canada. Tesla downgraded to 32A because of that.
 
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A caveat about using the 14-50 at 40 A: Many "14-50" outlets actually only have a 40 A circuit breaker, especially in Canada. Tesla downgraded to 32A because of that.
My "50 amp" extension cord was actually only sized for and rated at 40 amp when it arrived. Nice thing about 32 amps is there's a large margin of safety on most circuits and setups. Especially important when charging at random places where you don't know the quality of the wiring, breaker size, etc.
 
14-50f to TT-30M (for certain campgrounds)
What exactly did you buy, and where did you buy it from, and have you tried it yet? I am asking because if you bought just a regular one of those cables that from like camping supply/RV equipment places, it definitely will NOT work for charging your car. It won't harm anything, but the car will just see 0V and not do anything. You would need to buy one that says it is specifically wired for EV charging. It's because those are having to do a little trick with placing the wires differently to use the 120V connection through a 240V outlet type (14-50). The camping ones just put the same single hot wire on both of the two supposed hot connections, so there is no voltage difference there that the car can use.
 
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