OSR: 1d50 Missions for Small Groups of Medieval Mercenaries

As a late medieval mercenary, your time is divided between:
  • waiting around (something D&D can skip).
  • fighting a mass battle or siege (something D&D traditionally has trouble handling without switching to wargame scales).
  • staying alive.
  • having a good time.
Here are 50 missions for small groups of mercenaries (3-10 people, the size of a traditional D&D party).

Of course, ElfmaidsandOctopi got there first.

Jakub Rebelka

1d50 50 Mercenary Missions
1 There's a legend about that castle. They say, on the summer solstice, a fifth tower of pure gold appears at noon. And it's the summer solstice tomorrow...
2 For diplomatic reasons, you need to sack and burn this monastery while dressed as mercenaries from a rival company. Make sure you leave survivors. And don't loot anything too obvious.
3 See if you can find a path through that swamp. Map it or use markers. You may need to find a local guide.
4 This convent of nuns has a very important relic. Go steal it for the greater glory of the mercenary company. If the saint doesn't want to be stolen, you'll get smitten by lightning or something equally unpleasant.
5 The emperor of some foreign land is sending wax copies of his legs to a nearby city for custom-fitted armour. You're going to steal them and we're going to hold them for ransom.
6 The emperor of some foreign land wants to add a local beast to his menagerie. Go capture something magical and dangerous. Here's 50' of rope and a wooden mallet.
7 Our leader's favorite lover is very sick. A famous elderly physician resides two towns away, but refuses to travel to the camp despite offers of vast wealth. Go kidnap the physician... politely.
8 One of the Archpriest's legates is carrying secret letters to a nearby city. Insert this sealed letter among them. 
9 We need you to paint insulting slogans on these dead and diseased cows before we launch them over the walls.
10 There's a small castle along our line of march. It would be convenient if it was occupied before the bulk of our forces pass by. Bribe, fight, or bluff your way in.
11 Here's a laugh. Go ride out to this castle and tell the owner to surrender or we'll burn it at dawn. We won't of course. Too much trouble and it's too far away. But the owner might fall for it.
12 Apparently the queen of this town has a magic mirror that identifies pretty women for her. Weird, I know, but think of what we could do with that mirror! Go steal it.
13 There was a silver mine in the hills before the war. See if any of the locals remember where it was. It might still be operating. 
14 The court poet from a local city has written some very satirical verses about our leader. It'd be unfortunate if the poet met with a tragic accident on the road.
15 The enemy army has camped on a plain just below a dam. If someone breaks that dam, the river will burst its banks and sweep them away. Of course, it's behind enemy lines...
16 One of the Archpriest's legates is carrying vital letters. You need to steal them, copy them, and return them without the legate noticing.
17 Feint a night attack on this town, just to annoy them. Don't get killed, just make them raise the alarm.
18 The captain says he needs a tutor for his children. Go find someone suitable. A literate priest or something. They may need some persuading to work in a mercenary camp.
19 We've tried undermining the town's walls, but something keeps eating the miners. I mean the miners keep disappearing. Anyway, if you sort it out you'll get a nice bonus.
20 It's vitally important, for diplomatic purposes, this convent of nuns is protected. Make sure nobody bothers the nuns. That includes you. And keep your hands of their relics.
21 The enemy town has hired unbribeable killer mercenaries from Foreign Parts. They don't speak the local language so we can't corrupt them. Find someone who speaks their language, and quickly!
22 Our leader is hosting a banquet. Ride down to the coast, buy fresh fish, and get them back here before they start to smell. 
23 Our leader's astrologer-wizard started gibbering about "moondrops" and "beams of silver" and ran off into the night. Go find them and drag them back.
24 We need to bulk up our numbers before the assault. Go see if any of the local villagers can hold a sword or a spellbook. If they can and they want to fight, sign them up. 
25 Our leader is getting married. You lot need to get him a gift. Go steal something nice off the registry.
26 Remember that old manor house we took in the spring? Apparently there are tunnels below it. Some of the guards went in; only one of them made it out. Died in a tavern three days later, but his pockets were full of gold.
27 Go scout the enemy army and count their cannons. Don't get caught.
28 This fog isn't natural. It's a wizard business. Or a druid. Or worse. Head that-a-way and see if you find anything. We'll light a signal fire to guide scouting parties back home.
29 Here's the plan. You pose as deserters, sneak into the town, and spread the word that it will be violently sacked tomorrow. The nobles sneak their valuables out. We ambush them and share the proceeds.
30 Someone massacred a village and it wasn't us. Go take a look.
31 The wizard's tower is supposed to be empty, but something in there keeps lobbing spells at our troops. Fix it.
32 You look like clever people. Invent a terrifying weapon to impress our employers. It only needs to work once, during the demonstration. You've got a week.
33 You're our last hope. Get inside the town somehow and open the gates. 
34 To prevent the enemy from marching against us, set fire to all the grassland from here to the mountains It's been a dry month. Their horses will starve.
35 Some moron says he found "giant bones" down by the riverbed. There haven't been giants in these parts for centuries, but I hear a powder made from their bones makes your... well nevermind. Just go find them.
36 We're running low on horses. Go into the hills, find a village, and see if they've got any horses.
37 Go check on the condition of this road. Rumour has it goblins were seen in the trees, and where there's some goblins there's always more goblins.
38 See that hill? There are standing stones on the top with strange markings on them. Might be nothing, but you should check them for wizard business.
39 Our leader's worthless bastard son turned up. Take him on a "hunting trip" in the hills. I hope nothing conveniently tragic happens to the poor lad.
40 Your job is to deliver this letter to the leader of a rival mercenary company. Don't stick around for a reply. No seriously, it's best if you hand the letter to their leader and run.
41 We're running low on food. Go into the hills, find a village, and get as much food as you can. Take these two carts.
42 They say a tunnel went through that mountain in ancient times. Go see if you can find the entrance. It's not likely-smarter people have tried-but if you do you'll be legends.
43 They say there's a hidden village in the hills, inaccessible unless you know the path... or you're very smart. And you're very clever, right? Go find it and see what they're up to.
44 So we might have accidentally killed a bishop and his retinue. You could have been his twin. Put on this hat and robe, go where he was going, pretend to have a fever, and die of natural causes as soon as possible.
45 You need to fake a troop movement away from the camp. Convince any observers watching by night that we're sending a detachment to flank them. No, there's no budget. Figure it out.
46 The people paying us say we can only claim territory up to the border. The border stones are moveable if you've got a pickaxe, three oxen, and a cart. You only need to move... oh, two dozen. A mile or two will help.
47 An ambassador from a distant kingdom was kidnapped by some bandits. They're hiding in a small looted castle. The local nobles want the castle back but can't pay. The ambassador's ransom is unlikely to arrive.
48 A rival mercenary company just purchased a huge stock of gunpowder in preparation for a predicted siege. It'd be a real shame if someone set fire to it.
49 Old Simpkins, who sells us onions and those funny woodcuts, says bandits have been bothering him near the pass. Go sort them out. We like Old Simpkins.
50 A noble in a local town is stirring up trouble. Go assassinate him. Quietly, publicly, doesn't matter.


  1. Great fun, and by the end of this list I've got a fairly clear mental image of the sergeant giving out these assignments. :D

  2. Undeniable proof that dubiously-moral characters deal out the best quests!

  3. How long did you take to come up with these? What sources did you borrow from?

    1. About 2 weeks of jotting down notes. Too many sources to list directly, but "The Devil's Broker" and "Captains of Fortune" were already covered on this blog. I'd also recommend "Mercenaries and their Masters" by Michael Mallett.

  4. These are disgustingly good.

  5. This is essentially a campaign in a post. You do 5-10 of these and some narrative will emerge. Great work.

    1. That's the plan. Why plot a campaign when a few good tables can do it for you?

  6. "We need [X], go get it, there's no budget but we don't care how" is the perfect problem-solving quest. Horses, food, spectacle for the employers, whatever it is, we just need it. Although "pretend to be a bishop and then die of natural causes" is an absolute treat!

    1. I love the bishop one, I laughed out loud a few times while reading this list :)