Oblivion:Highwayman

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Highwayman at Fort Ash

Highwaymen are a specialized variety of Bandit that you will encounter along the main roads. They are always male Khajiits. You will only encounter a single highwayman at a time. He will stop you instantly, even if you are running at full gallop on the fastest horse money can buy. He will always start by talking to you and offering you some options:

You can give him 100 gold.
If you tell him to try and take it from you, he will attack. You can kill him, or if you have a horse, simply run away, he can't keep up for very long, and will usually run into guards on the road, who will take care of him for you.
If you appear poor (specifically, the value of your clothes and armor is less than 10 gold, and you have less than 100 gold), you can plead poverty. This may result in the Highwayman attacking you anyway, however.

If you pay the Highwayman, you can pickpocket the money back - and he doesn't care - nor will you have a bounty, because of the Highwayman's low responsibility.

In certain situations, it is possible that a highwayman will forcibly stop you, but then will not ask for your money, allowing you to continue without paying him or fighting him. Specifically, this will happen if one of the following conditions is met:

If you are a full vampire (100% vampirism) and his Disposition towards you is less than 100 (if he's not terrified of you, he'll still rob you).
If you are wearing the Gray Cowl of Nocturnal.
If you have completed the Main Quest, there is a 2-3% chance (depending upon disposition) that a highwayman will be friendly. Furthermore, if he is the first Argonian or Khajiit you have met since completing the main quest, he will always say:
The bards will be busy composing songs in your honor for years to come. To think that we lived through such times!
If you have completed the Knights of the Nine questline, there is a 20% chance that he will greet you as the Divine Crusader or as Sir Knight. The exact greeting will vary depending upon his Disposition towards you. This option can even be triggered if you have gained infamy since completing the questline (in which case he is disgusted by you).

[edit] Guaranteed Highwaymen

At these four locations, you have a 100% chance of meeting a highwayman. Each of these highwaymen will only appear once; after you have killed them, they will never respawn.

On the Chorrol side of Fort Ash on the Black Road.
At the north end of the Yellow Road bridge over Panther River.
On the long Red Ring Road bridge across the Upper Niben at the southeast corner of Lake Rumare.
On the Gold Road north of Anvil at the turnoff for Lord Drad's Estate, next to a stone wall.

[edit] Possible Highwaymen

At these two locations, you have a 50% chance of meeting a highwayman. These two highwaymen can respawn if you later revisit this area, again with a 50% chance.

In a rocky defile on the Gold Road east of Skingrad.
At the nameless fort-style tower on the Red Ring Road at the northeast corner of Lake Rumare, just down the hill from Fort Chalman.