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First Road Trip (2014 S60)

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Try 45 psi. Something is off.
I did a 2500 mile trip from Houston to Orlando and back in March and the Car NAV and EV trip planner.com were within 1-4% of actual SOC estimate by the time we arrived at the next SC. This was in a loaner MS 60D (75D battery) and 45-46 PSI in all tires and we typically drove 3-10mph over posted speed the entire way (excepting traffic). Only time the SOC estimate was wrong was when the temps dipped into the upper 30's one night, then the SOC was off by 8% (arrived at 14% when estimated 22%) and tire pressure dipped to 42...hmmm. What tires do you have on your car? Continental Conti-silent was on the loaner. We had 600+ lbs of people and luggage in the car as well.
I have the stock Goodyear Eagle Touring tires with less than 600 miles on them. I'll give the Tesla Service center a call tomorrow to possibly take it in also. I don't have any other trips planned until after October, so it may be a while before I can even attempt to make an additional comparison.
 
We came up 95 yesterday on our first road trip in our MS 60 (Dec 2016) and with the TACC set on 80mph, we did fine on range - averaged 75 mph in traffic with wife and kid in car, plus a back full of luggage. That much of a range reduction really does sound off since our range stayed pretty much as rated.
 
My 2014 S60 seems to be much slower charging than the OP's: takes over an hour to get to 90% from a low SOC. Nevertheless, I get a bit better range than he did at highway speeds. Certainly 70 mph takes a lot more rated miles of range than the actual distance. I agree with the others that 42 psi is too low for tire pressure, despite what the door placard says. The car might need an alignment as well.

I've done 1000 to 2500 mile road trips pretty routinely in my S60. It takes some care and watching the energy trip plot when doing longer legs of the trip: 140 to 150 miles. I can't do those at the 80 mph speed limit in my car, especially when there is an elevation gain (not a problem in Florida though). I have to work at it in ways that the larger battery cars don't and my charging time is double (or more) so it takes longer, but the S60 works for road trips well enough.

I think that the OP needs to learn to use the energy trip plot for road trip legs. Charge to a buffer of 20%, if possible — that's when the trip plot projects that one will have 20% left before leaving. [The trip plot seems to be based on low highway speeds of 65 mph or less IME.] On a leg of 100 miles or less even a 15% buffer is usually enough, barring headwinds or something like that. For a long leg of 140+ miles even a 90% charge in an old style S60 might not be enough to make it at 70 to 80 mph. But slowing to 65 will usually work. The key is to slow down soon when the energy projection starts falling for several minutes. You can always speed up a bit later if the plot stabilizes or you know that you have the next stop made (that becomes increasingly obvious as you get closer). With experience, it becomes easy to manage longer trip legs and the short ones are no problem at all. Just don't think that 150 rated miles on the battery gauge means that one can go 150 miles at 70 mph or more. Those highway speeds use range at a faster rate than EPA rated miles, even in mild weather with no heater or AC use.

My 2¢.
 
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Reactions: OBX John
Try 45 psi. Something is off.
I did a 2500 mile trip from Houston to Orlando and back in March and the Car NAV and EV trip planner.com were within 1-4% of actual SOC estimate by the time we arrived at the next SC. This was in a loaner MS 60D (75D battery) and 45-46 PSI in all tires and we typically drove 3-10mph over posted speed the entire way (excepting traffic). Only time the SOC estimate was wrong was when the temps dipped into the upper 30's one night, then the SOC was off by 8% (arrived at 14% when estimated 22%) and tire pressure dipped to 42...hmmm. What tires do you have on your car? Continental Conti-silent was on the loaner. We had 600+ lbs of people and luggage in the car as well.
There is a really big difference between an old S60 from 2014 or earlier and a 60D with a 75 battery. The old S60 has a smaller usable battery, is much slower charging, and is less efficient when driving at highway speeds. The two cars are not really comparable IMO.