How compressors work: most have a built-in switch that turns the motor off when the tank reaches a maximum pressure, and then turns the motor back on when the tank reaches a minimum pressure. So, you turn the compressor on and it starts filling its tank. If your limit switch is not adjustable, it will run until the tank reaches 110 psi, when it shuts off. Now you connect the hose to the tire and open the valve - if the tire has 90 psi in it then the tank will attempt to push more air into the tire. But, the compressor's tank may not hold enough volume to increase the tire from 90 psi to 100 psi, and the pressure in the tank will drop - eventually the tire and the tank will be at the same pressure and no air will flow either direction.
Here's where the minimum pressure switch comes into play - at some point the pressure in the tank drops below the pre-set minimum pressure and the compressor will come back on to replenish the air in the tank. But, if the tank and tire have equalized at some pressure above the mimimum, it will never come on so you're stuck with that pressure. You need to stop pumping air and release some air from the tank so that the compressor can refill the tank. Remember - the tank MUST be at a higher pressure than the tire for air to move from the tank to the tire...