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how do you make the game recognize that you're in six challenges at once? after trying a few combinations, I put myself in IC1 and IC3, meaning I was in both of those as well as PC1-4, but I still didn't get the achievement for being in six different challenges at once

You need to "enter" 6 different challenges and complete IC1 to get that achievement. Trapping doesn't count towards the achievement requirement. Maybe I should have made that clearer.