Depends, how are you determining whether it's dry? The top of the soil is very deceiving - it can be dry and cracked like the desert during a drought, but just under she surface a few millimeters, it can be the perfect amount of moisture.
I have a series of checks I perform to see if the soil is actually "dry". Having wet soil on top could be an indication you're overwatering.
I push around some of the dirt on top. If the soil is "moist" (not wet) within the first 3/4" - 1.25" of the soil line, then the plant has plenty of moisture. I also look at the drain holes. If the soil is still moist at the drain holes and the cup is still somwhat heavy, I know there is sufficient moisture in the soil. If I put holes in the side of the cup (as I usually do), I look at those holes to check for moisture also. Just feeling how heavy the cup is (like JD talks about a lot) is terribly helpful in knowing how much water is retained.
The key point to remember when dealing with rooted cuttings is that they don't need a lot of water, they need the soil to be moist, not wet. Wet soil is bad. Moist soil - think of a nice moist cake - is perfect. The trick is to have the proper discipline to stop yourself from watering, which is something a lot of people fight with.