If I put two Cloak of Confusion on a creature card and it is not blocked, can I have my opponent discard two cards at random?


You can use multiple.

Going by the Oracle wording, which is the only wording that counts, the ability on Cloak of Confusion is a triggered ability; so when the creature attacks and isn't blocked, both abilities will go on the stack. You can order them however you want (it makes no difference as they are identical), and when each one resolves, you can choose to make your opponent discard a card at random.

Note that if you were to only choose the "you may have it assign no combat damage this turn" for one of the two abilities; the creature would still assign no combat damage, and your opponent would only discard 1 card. So you would want to make the same choice for both abilities.

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