If the players put to use their own character abilities or strategize in a way that trivializes your encounter, you should definitely throw them a bone every now and then. In your rooftop example you can alter scenario 3 a bit, then if you think of a way to castle would respond to a rooftop incursion, you are all set to continue. When the party then surprises you with option 5 you had not considered, it is fine to ask for a short break while you adjust what you had planned with what they are doing. Having a few ideas on how to approach each of these.
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