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During times of pure incompetence, ineffectiveness, or stupidity, this refers to how much a person is struggling with a given situation, or possibly with life in general. The more intense the struggle, the deeper they are in the box.
guy 1: "dude, i couldn't get it up last night and she totally bailed on me."
guy 2: "bro, you're deep in the struggle box."

watching a completely hammered girl attempt a lap dance, then proceeds to vomit, one might say:
bystander: "wow, she's DEEP in the struggle box!"
by obuhanick November 05, 2009
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