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Most Difficult Dark Brotherhood Quest


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I'm not entirely sure, but a likely candidate would be the "Scheduled for Execution" quest. I thought it was kinda challenging sneaking past the guards, not to mention actually killing the prisoner without killing any of them. I found this questline to be pretty easy though.
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The Draconis contract was quite annoying, though not particularly difficult. I experienced something strange during that quest though. I though the hostile conversation options with Andreas Draconis were not subtle enough, so i waited until the nearby guards was drunk or in a different section of the inn, and attacked him in his sleep. The guard ran in, and both he and Andreas attacked me, so i ran out of the inn and fast traveled to some town. I must have been pretty far away from the two of them, or fast travel would have been prevented. When I arrived in the town (Leyawiin, I believe it was), Andreas was there also!
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Yeah-- definitely Scheduled for Execution. That was also the one that I enjoyed the most, just because it was the best challenge. The "Bad Medicine" one was a good challenge too, though not quite as tough, I thought. Really, all of the first set of DB missions are challenging and interesting.

 

I guess there could well be a tough one in the later ones, but I doubt it. I wouldn't know though, since I lost interest in the DB questline after the dead drop orders started. I tend to believe that Bethesda just tacked those on late in the development process to pad out the questline, since there's not only no interaction (other than picking up a note) but the missions themselves are dull and uninteresting. Rather than being intriguing and complex missions, they're just tedious hack and slashes, and after the first few I just stopped doing them.

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gpstr 1, you will have a couple interesting quests after completing the.. seventh dead drop orders i believe it was. The gold you receive is also quite substantial. P.S "Bad Medicine" was a pretty fun quest. The annoying thing was that during my early attempts at the quest, i succesfully placed the poison bottle in the cabinet, but the guard found my charcter right in front of the exit door.
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  • 8 months later...
To me the hardest ones were Scheduled for Execution and Next of Kin (where you have to kill the entire family. I never managed to kill that guard female in one hit so I always ended up with bounty on my head.)
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Killing Adamus Philida. I had no problem with Scheduled for Execution or Next of Kin, but Adamus makes it difficult. You have to find perfect location in Leyawiin from where to shot Rose of Sithis while dozens of guards are walking around the town. Also, (don't know how) Adamus always see me. It's really painfull quest.
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You know it's funny. Once while tracking Philida down I arrived in town late at night and missed the time where I was 'supposed' to kill him. For kicks I decided to try and find where he was staying. I entered the guards barracks and was snooping around when I heard someone walking downstairs. I ducked into a side room, cast an invisibility spell and waited. The door opened and it was Philida! Not wearing his armor! So I put an arrow in his chest and went home satisfied.

 

Back on topic: Sheduled for Execution gave me trouble the first time I played it through. I was level 2 or 3 and had NO sneaking skills to speak of. Since then I always leave the sewers a master of sneak. :D

 

-Razorpony

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Killing Ungolim was the most difficult for me. This seemed like it would be an awesome assassination: skirt the shadowy Bravil rooftops in the dead of night and wait for him to kiss the Lucky Old Lady for the last time. However, he seemed to auto detect me as soon as I entered the city gates, even if he was on the complete opposite side of the city! (I have 100 sneak skill) First time, he was killed by the guards. I didn't want that, so I reloaded. After many, many tries at different times of day, I still was constantly greeted by battle music. Finally, I was forced to do something I really didn't want to do: 100% chameleon. First I tried entering the city with it, but uncloaking once I reached a vantage point. Ungolim would still detect me as soon as I uncloaked, even if I wasn't in his line of sight. Finally, I used chameleon for the entire assassination. It worked, but it really felt cheap. Any two-bit assassin can turn invisible and kill someone. I wanted the satisfaction of killing without witnesses or magic tricks. It takes true skill to disappear without magic. Ungolim must have had some hardcore detect life enchantments. :dry:
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