The wines are from different years If you apply an arbitrary order to the bottles, the number of possible year-arrangements of the bottles is 16! Each tes

The wines are from different years If you apply an arbitrary order to the bottles, the number of possible year-arrangements of the bottles is 16! Each test gives you one bit of information Since 2^50 is only greater than 16! by about 50x < 2^6, you only have about 5 tests to spare. There's probably some clever way to express the solution beyond just the brute force the above implies, but I haven't thought about it past this point