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psi reading on my tires is not accurate, car says they are 37-38 psi, I connected my compressor to it and it says 33.5 psi

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It’s a new compressor though
A high end professional compressor with a pressure gauge calibrated by an independent third party lab? Or a disposable piece of junk $15 compressor from Wal Mart?

In my experience (2 Teslas, 2 sets of wheels/tires/TPMS sensors, so 16 TPMS sensors total) the Tesla TPMS tire pressure readings are spot-on.
 
I think it's the compressor nozzle. If you the compressor type that screws in nozzle, I think that's a little bit better. If you have the compressor nozzle that pushes in with a latch, it probably is sensitive to how much you push onto the valve stem before closing the latch. This probably will affect the reading on the sensor.
 
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The car does not give a range 37 to 38 as the thread title suggests. It either says 37 or it says 38. So far only two sources have been used, the car and a compressor. A dedicated PSI reader can also be used. It is doubtful that any reading is 100% accurate and highly likely that 10 readings from 10 devices will show 10 different readings. Unless it's way off as compared to your compressor, use the car reading as the definitive value. Adjust your use of the compressor to get the reading you want from the car. That's what I do. I use the reading of almost 44 on my compressor to get 42 in the car's reading.

Edit: my bad. The title relates to the reading of all four tires, each one either being 37 or 38.
 
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A high end professional compressor with a pressure gauge calibrated by an independent third party lab? Or a disposable piece of junk $15 compressor from Wal Mart?

In my experience (2 Teslas, 2 sets of wheels/tires/TPMS sensors, so 16 TPMS sensors total) the Tesla TPMS tire pressure readings are spot-on.
It’s one of those portable ones you can plug into an outlet, I like them for road emergencies I can fill up anywhere I am, $50
 
Looks like the compressor or car is off by 4 psi, compressor said I put in 40 psi car says the tires are 44, so next time I’ll put in 38
That's what I do when topping off with my $15 Wal Mart compressor (I keep one in each car).
The PSI reading in the car is not real time unless you’re driving. Whatever you’re seeing is from your last drive, so that’s one possible reason for the discrepancy.
Good point - it will show "2 hours ago" or something like that if the sensors are asleep. They do stay awake for a few minutes after you stop; I can often double check my readings through the front window as a fill up each tire.
 
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I've got a $100 (without battery) Milwaukee compressor and it's a good 2-3PSI out most of the time.
The gauge on a compressor is just a guide. You use it to put air in just above the pressure you want and then use a separate quality gauge to set the pressure.
 
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Since I over filled these tires a little at 44 psi when the recommend is 42 I’m not going to blow a tire going down the interstate or anything am I?
The sidewalls will list a max load @ max pressure. Probably @ 51PSI cold, so you're fine.

Tire pressures are spec'ed and measured cold (after several hours of rest). Best to measure in the morning, or a cloudy day, They will warm due to friction while driving or sitting in the afternoon sun, with a resulting increase in pressure. Do not bleed off this increase in pressure, or you will be underinflated. 51PSI cold means they are designed to handle more than that when hot.

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