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The Elder Scrolls IV: Shivering Isles Hints
How does this routine work?
1 of 9: Talk to Haskill at any time about "Defend the Realm" to have a chance at learning of an attack on either the Gates of Madness or one of the settlements.
2 of 9: If he says all is peaceful, simply choose the same dialogue option again and again until an attack happens. (Note that this only seems to work when you're talking to him inside the palace.)
3 of 9: When he says that an attack has been reported, you can say whether or not to send guards to deal with the matter.
4 of 9: Either way, you need to go to the place under attack to see that things get handled properly.
5 of 9: If you don't have any guards sent, you'll have to finish off the attackers yourself. (Except at the Gates of Madness, where the Gatekeeper will be a big help.)
6 of 9: When all of the attackers are dead, you'll get a message to that effect on the message line at the top of the screen.
7 of 9: Return to Haskill (or summon him with your Summon Haskill lesser power) and talk to him about "Defend the Realm" to get your reward.
8 of 9: It'll be 1000 gold if you didn't have any guards sent, and 500 gold if you did.
9 of 9: You can now ask him about "Defend the Realm" again to have a chance at a new attack to handle.