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You have to fix the telescope in the castle to see him. Then at night time, his hideout is shown on the map.

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alright how do I go about fixing the telescope I think I figured out part of it I ended up getting the plunger and used it on the telescope at general grants and then it broke and now I’m stuck what do I do next so i can get to the dragon boss?

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Looks like the devs answered it in another thread https://itch.io/t/2038938/fix-the-telescope