Often, if I'm cooking something in the oven that involves bacon, I'll partially cook the bacon in a frying pan first. You don't want to fry it crisp. Just enough to render off some of the fat. It will then be more likely to finish cooking and crisp up in the oven.
I've done this with both bacon wrapped tenderloins and jalapeno poppers, and it works great.
I simmer my bacon in a little water about 3-5 min before wrapping anything that way it cooks and crisp up a lot better.
Example: I make jalapeno poppers and little cocktail wieners wrapped in bacon as these don't take long to cook but the bacon takes longer.