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Installer recommends an electric garage heater. Is it necessary? I’m in the Chicago land area

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What else is the electric contractor trying to get you to agree to so he can tilt extra money his direction? A heater(s) would be for humans working in the garage. Unless you have a winter workshop in the same space, I would be suspecting shenanigans.

I charge outside, in the winter, in Chicago. Haven't had a problem yet.

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OP, Looks like they’re trying to upsell you.

Using a garage heater during winter can improve your Tesla's charging efficiency and battery performance, as cold temperatures can reduce charging efficiency and range. While the wall connector is designed to operate in a wide range of temperatures, extremely cold conditions could potentially affect its performance or longevity. Heating the garage can mitigate these effects, leading to faster and more efficient charging, though it will consume additional energy.

However, a garage heater is not mandatory since Teslas and their charging equipment are designed to function in cold environments. The car’s built-in thermal management systems and features like the Cold Weather Package help manage cold temperatures. Benefits of a heated garage include increased comfort, reduced wear and tear on the car and charging equipment, and faster charging times. Balancing these benefits against the additional energy costs is essential. If you frequently experience extremely cold temperatures and want to maximize charging efficiency and comfort, a garage heater could be a worthwhile investment.
 
Not getting the hate for the electrician. It’s a quote, not a demand. I’d think the options here are to select the items you want and not what you don’t. Certainly there are folks who would opt for it as well as those who wouldn’t especially in colder climates.
 
I'm in Maine, and my 3 has lived outside in a temporary carport for the last 5 ½ yrs. It's doing great. No issues, minimal battery deg. Everyone tells me the battery likes it cold.

Strangely, before Maine, I lived north of Montreal in Quebec province, as a boy, over 50yrs ago, and garages were not at all common. And heated garages, I don't remember any. I remember driving around on a skidoo right down the main roads when it was really snowy, and going thru red lights after midnight, cause dad said it was optional. Maybe there's a difference between the big city and small towns, but no, I don't remember heated garages.
 
Not getting the hate for the electrician. It’s a quote, not a demand. I’d think the options here are to select the items you want and not what you don’t. Certainly there are folks who would opt for it as well as those who wouldn’t especially in colder climates.
Same reason a lot of Tesla buyers, myself included, prefer the Tesla buying experience to traditional car dealers. Upsells are annoying.
 
Same reason a lot of Tesla buyers, myself included, prefer the Tesla buying experience to traditional car dealers. Upsells are annoying.
Yeah, one-time gain for subsequent life-time of service pain, inordinate delays, and whimsical warranty denials.
With the good comes the bad: OEM-owned service centers that are obligated to take the side of the manufacturer's, not the customer.
This lunch isn't free!