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The Elder Scrolls V: Skyrim Hints
Meet Irileth near the Western Watchtower.
1 of 3: Follow Irileth out of Dragonsreach and down to where she talks to some soldiers. After that, follow her outside and down to the western watchtower.
2 of 3: NOTE: If you don't follow Irileth out of Whiterun, you can go meet up with her whenever you're ready. Check the world map to see where the Western Watchtower location is, then look just east of it for a quest marker that shows the rendezvous point. There'll be another quest marker showing Irileth's current location.
3 of 3: After Irileth runs up the watchtower's large ramp, go past her and enter the tower. Quicksave, then wait for the next objective.