Ben-
First off- congrats on getting an Oscar. I'm a fellow Oscar user.... but not a professional troubleshooter of it. Although I can provide a few simple steps and tips. I'm going to assume your a 1st time user and complete noob with this so forgive if you already know these items.
1. Doesn't heat:
a. When you first turn on the unit does the "heat" light turn on? This is the light/indicator below the "water" indicator. Keep in mind that on initial turn-on and subsequent indication that the heat light is off there will also be false pressure which is "relieved" by opening the steam wand momentarily till the heat light turns on again. It takes at least 15 min for the Oscar to come to full heat. If the heat light doesn't turn on then you
may have the same problem I'm having:
Oscar heater won't turn on after descale. I've email nuova simonelli in Ferndale, WA and am waiting for an answer. If/when I do get one, I'll be sure to update the thread. I hope for your sake it isn't similar to my situation but it doesn't sound like it.
b. If you're lucky, the high temp limit switch was tripped. If you're facing the front of Oscar, on your right hand side of the boiler, somewhat towards the top, approx 12 o'clock is a white electrical gizmo with usually a red button. See if you can press this button in.
2. Water indicator: There may be something blocking the reservoir thereby preventing water to be drawn into the sensor. You'll have to remove the top again for this step to make it easier.
Remove the white plastic water tank and you'll notice the receptacle on the bottom that accepts the reservoir - there should be water inside this little reservoir; it probably holds a few teaspoons of water in it. Check the bottom of the white tank - it has a check valve in it- if you push on it water should come out. Possibly you have some gunk in there that prevents water from coming out and the water sensing unit from sensing that there is water.
Fill up the tank again, reinstall it and turn on the machine. Turn on the pump and note whether water is pulled from the water tank.
If when you initially turn on the machine the pump turns on this is the machine sensing that the boiler needs to be filled. If not then the boiler is full doesn't need to be refilled.
If you only had to do step 1b above then all should be well for you.
Good luck