Rules FAQ
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You can place a character without shadow in shadows. It will not gain the shadow keyword, but it can still come out of shadows with cards like Starfall Spy, A Traitor's Whisper, or Doran Martell (AHaH).
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The reaction to being discarded from shadows can be triggered from the discard pile. It shares the reaction window cards like Edric Dayne (HMW) and "Widow's Ford". However, you have to trigger Hidden in Shadow first if you want to draw a card, otherwise it will no longer be in the discard pile to be triggered.
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If you discard Hidden in Shadow with The Shadow City, you have to react to the cost of The Shadow City first, which means drawing a card for Hidden in Shadow before you draw the 2 cards for The Shadow City.