Where is the portrait of the sheperdess.? Is she the portait covered by the red banner?
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If you go to the Transfiguration Courtyard, then head towards the door that leads you to Herbology, but once past that door, go left instead of right (right will take you to Herbology). Taking that left will bring you to an entryway on the right that leads to a staircase. If you go up the first chunk of stairs, the shepherdess portrait will be directly in front of you on the landing. It will be up on the wall, unlike the secret passageway portraits that touch the ground.
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