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In the interest of having my apps in as early as possible, I've been working on them over the summer. I'd like to knock out my UPenn essays, but I don't want to write them if the topics are going to be different this cycle. Does anyone know if they're usually the same, or if they change every year?

nominally they do change. Write a Why Penn essay and be prepared to tweek it for the exact question of the year. The substance of your essay should be easy to adapt to whatever they ask.