96 Monte Starting issues and Tranny problems

I have a 96 Monte Carlo that has some faults...

1. Normally it starts just fine but every once in a while it just won't start. I turn the key and nothing happens, no cranking nothing. After I wait about 5 or 10 minutes it will start just fine. Any ideas what might cause this?

2. On occasion the car starts to lose tranny fluid. This normally happens when I drive for over 30 minutes. The engine light comes on and it shifts hard. I can easily fix this problem by just adding tranny fluid. Any ideas?

Thanks in advance,
Jeno

Welcome to AF, what is the cel code, get it read. Find the leak source and have it repaired, but wait for the code and addt'l diagnosis. When the engine won't crank does the security lite on the dash stay on?