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The Elder Scrolls V: Skyrim Hints
Kill the dragon.
1 of 3: If you've taken cover inside the watchtower, you won't be able to see the dragon much since it flies around a lot. It does occasionally land, but not necessarily within sight of the tower's doorway.
2 of 3: You could go outside and run around the tower, trying to use cover to avoid the dragon's fiery breath attacks while hitting it with your best ranged attacks. However, you'll probably get flamed sooner or later that way, and that'll kill you very quickly if you don't have any fire resistance from equipment or potions. The same problem applies to attacking the dragon from the tower's roof.
3 of 3: Fortunately, your Whiterun allies will be out there doing the dragon some damage, so you can just stay near the top of the ramp and shoot off arrows or spells from there whenever the dragon lands nearby. Eventually, it'll die, and you'll get the next objective.