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Need Approximately 55 Ft Of Cord

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You should not have a 14-50 installed, you should have a 6-50. As I understand it, the14-50 has an unused neutral wire. This makes the wire more expensive that it needs to be, raising the cost of your installation. This also makes you extension cord heavier, stiffer, and more expensive than it needs to be. There are 6-50 extension cords readily available for the EV and welder market. There is a 6-50 adapter for both versions of Tesla's Mobile Connector. My 2 cents.
 
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Here’s a diagram. The reason for the Tesla being far back from the garage is to leave room for the car in the garage to get in and out. Yes it would be backed in.

I see. Depends on where the edge of the driveway is relative to garage door edge, but that seems like an impossible situation.

I checked the Wall Connector cord in this configuration; it would not be long enough to make exiting the garage comfortable, unless you could park the Tesla way to the left somehow.

I have no solution other than an extension if you cannot install an outlet outside. As others have mentioned, you should go with 6-50 not 14-50. Extension cords will be cheaper (and lighter) as well. I just went with 14-50 for my install “just in case” and it was a few years ago before I understood what was needed.
 
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Here’s a diagram. The reason for the Tesla being far back from the garage is to leave room for the car in the garage to get in and out. Yes it would be backed in.

I picture is worth a thousand words.

A wall connector on a post would be a very nice long-term solution. A 50 amp extension cord will get the job done, but it increases the fire risk due to the multiple connections (points of failure). People have reported some scary things happening with 14-50 outlets, even without extension cords. Considering the high value of your vehicle collection, I think it's worth spending a little bit extra on a permanent charging solution.

NEMA 14-50 Plug Meltdown / Near Fire
My NEMA 14-50 nearly caught on fire Friday night!

That said, if an extension cord is the only way you can make it work, go with something like this: https://www.amazon.com/Cynder-Camper-Electrical-Extension-Handle/dp/B078M7ZFHN/
 
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I would not use an extension cord for permenent home charging under any circumstances. Here's my suggestion:

1. Plan to have the circuit run as close to the car as you can.
2. Use a rope (or a regular extension cord) as a cord proxy to figure out how long the cord really needs to be in order to reach from that closest point to where you are going to park the car. Don't plan on having the cord stretched tight enough that it hangs in the air. It should lie mostly on the ground...but you would need that anyway to get it under the door.
3a. If the wall connector with the 24' cable will work, then get one of those and wire it in.
3b. If not, send your UMC to QuickChargePower to have the cord lengthened enough to reach.

Tesla UMC extension
 
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