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At the beginning of the computer game before you enter the Land of Darkness, you need to find Sam's lunch box, flashlight, and mask. Any of these items can be found in the trash can, behind his scarf, under his bed, under his rug, or in his drawers. Once you enter the Land of Darkness and the Customs Inspection trees take his things, Pajama Sam's mask can either be found under a dancing couch inside Darkness's house, or it is being worn by a carrot. To find the carrot, you must take the boat straight across the river, pass some trees with the hollow log disguise, and go all the way back to a garden next to the wishing well.

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Q: Where is pajama sam's mask on pajama sam don't fear the dark?
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