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The Wikipedia page of "oracular statements from Delphi" lists a few accounts that might apply here. One example could be the Oracle of Delphi's counsel to Philip of Macedonia. He was told, "With silver spears you may conquer the world." The straightforward reading would be to make a whole bunch of spears made of silver and go to war. But Philip wisely decided to take control of nearby silver mines and use their wealth to bribe away his enemies' allies.
As for "outsmarting" the Oracle, Philip's son Alexander the Great is the clearest example. Originally, she refuses to answer his question of whether or not he would conquer the world. In response, Alexander began dragging her by the hair, and which point she screams "No more! You're unbeatable!" Satisfied with her answer, he leaves.
But probably the best example is from Plato's Apology. Socrates' friend poses the question to the Oracle, "Is there any man alive wiser than Socrates?", to which the Oracle straightforwardly answered "None." Socrates, rather than accepting the praise, tries to divine out the true meaning of the prophecy:
When I heard the answer, I said to myself, What can the god mean? and what is the interpretation of this riddle? for I know that I have no wisdom, small or great. What can he mean when he says that I am the wisest of men? And yet he is a god and cannot lie; that would be against his nature. After a long consideration, I at last thought of a method of trying the question. I reflected that if I could only find a man wiser than myself, then I might go to the god with a refutation in my hand. I should say to him, "Here is a man who is wiser than I am; but you said that I was the wisest."
Socrates then goes and interrogates men society considered wise, but finds their wisdom lacking. In the course of his investigation, he finally understands the prophecy: Socrates is the wisest man alive, because he is the only one who recognizes how little he actually knows.