One for sheer luck

Is this operation particularly bold or daring?

Is this operation overly complex or contingent on many factors?

Does the plan’s detail expose a vulnerability of the target or hit them where they’re weakest?

Is the target strongest against this approach, or do they have particular defenses or special preparations?

Can any of your friends or contacts provide aid or insight for this operation?

Are any enemies or rivals interfering in the operation?

Are there any other elements that you want to consider? Add or remove dice as relevant