You will only encounter a single Highwayman at a time. He will always start by forcing you into a conversation, which he can do regardless of your visibility or speed, as long as you're close enough. He will get down to business quickly, greeting you with:
- "Your money or your life."
- "Pay up, or else."
- "This is a hold up. Hand it over or die."
You will then have three possible options to choose from:
- You can give him 100 gold. He will happily respond with:
- "You're smarter than you look."
- "Good choice."
- "Thanks. Until next time, ha ha ha."
- The Highwayman will then take 100 gold from you and walk away. 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.
- You can tell him to try and take it from you. He will respond with:
- "Easily done."
- "Actually, that's the way this one prefers it."
- "We can play it that way if you like."
- He will then become aggressive and attack you. 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. He may accept your plea, responding with one of the following:
- "Why does this one always have to get the beggars?"
- "Times are hard when a robber can't even make an honest living."
- "That's fine. This one will kill you for free."
- If he responds with one of the first two options, he will not attack you or take any gold. If he responds with the third option, he will become aggressive and attack you. He will always respond with the third option if you attempt to plead poverty with clothing or armor that is worth more than 10 gold equipped.
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 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).
 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.
 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.
|Blunt||1 poison (25%)
3 lockpicks (25%)
- If you attack and kill a Highwayman before he initiates the conversation with you, the game will count your actions as illegal, and you will receive a bounty for either assault or murder. This is because a Highwayman is still considered a benign NPC before he talks to you.
- If the player chooses to pay a Highwayman when robbed, no gold will actually be removed from the player's inventory.
- This bug is fixed by the Unofficial Oblivion Patch.