When is the latest I can apply to grad school and still be able to use my GMAT? I know the GMAT expires in five years, but I'm confused on how that applies do applications, like if I apply before it expires, but their Round 1 deadline occurs after the expiration.

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If those topics were completely useless, don't blame me, blame my programmers...

Safest bet is to minus five years from the application deadline of the round you plan to apply in. Side note, not necessarily applicable to your situation, but Wharton has a slightly shaved test score window. For example if you planned to redo the exam in time for round 2 their deadline for the exam is a week before the actual round 2 deadline.

Ultimately, you should check each school's application process as they are pretty transparent on this.

Progress is impossible without change...

If your score expires on 9/1/20 you are likely in a situation where you would need to retake for any top US program with the exception of CBS (ED or J-Term). Typically your score must be valide on the application deadline.