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To reserve the vouchers you have to wait until wuwu is on screen with the dialog of "with our winner, wuwu, inside!" Then rest immediately after resuming though it only reserve like 100+ of vouchers than what I collect before rest but it works consistently on mine but give it a try!
"You only needed to answer the questions correctly!"
After that, it'll trigger 6 random questions, 3 seconds each, no mistakes allowed. You can do nothing on the first, but it will no longer be allowed after that. The bears wanna be seen as normal, so answer accordingly.
The corrupted bear form asks what color they are, wait until their the original color flashes before answering. This'll be asked twice by different bears, and it'll always be the first question. (That said, the flash happens infrequently so maybe it'll be too late before you can answer. Just try it again.) The rest of the answers should be easy: No squares, they're teddy bears, and they have one pair of eyes.
The very last question after all the random ones is all squares and the answers won't matter, but by then you should get the achievement. Good luck!