You need to understand the basic concepts of electricity. When it is time to fire, voltage builds up in the coil until it is high enough to force a current (flow of electrons) through whatever resistance is in it's way. That resistance consist of the plug wire, the air gap in your tester, the internal resistance of the plug, and the air gap across the plug's spark terminal. It then has to flow back through the engine block, to the source (coil). Now, understanding that, once the voltage is high enough to force the electrons across BOTH of the gaps you are presenting, it flows and you see it as a spark. Once that happens, the energy is dissipated and it's all over till next time.
Emphasis on BOTH air gaps in the circuit. If all other things are equal, it would make sense that the one plug has a higher resistance for some reason. On the other hand, the voltage may never be rising high enough to jump the resistances of both air gaps.
I understand where you are coming from with your question. However, if spark voltage is sufficient to jump just the 7/16" tester gap to ground (not through the plug also), that is the standard test. You are trying to combine that with the plug gap, and that is going beyond the normal test. Knowing the normally available voltage in the systems, I'd say it should be capable of jumping both though. May I suggest a possibly bad plug? Or a weak coil? Or a high resistance in that plug wire?