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How will Tesla Semi supercharge?

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If it's just a day cab, Level 2 wouldn't be as important. Longer term, L2 makes sense for sleeper cabs. If you're going to draw power, you might as well top off at the same time.
For stops that already have hookups, why not. Still need to drive to a Megacharger before or after the sleep stop though.
If new outlets need to be built, it might make more sense to build for a real overnight charge. 100 kW DC for a full charge in 8 hours.
100kW station? Where would they ever find such a charge site they could use?
I think the suggestion is that truck stops would put in appropriate overnight charging stations, for example 100kW ones.

But I still think it will be a while before electric semis move from being used by local delivery fleets and move to being long haul, that there is time for that infrastructure to get built out once they standardize on charging. (Most EV semis currently use CCS, Tesla Semi uses the MCS prototype 2 connector. Last I heard the final MCS connector/protocol hasn't been ratified yet.)