How many flavors of “bandit encounter” are there?

[gbaji]

Yeah. I tend to view NPCs choosing to attack an adventuring party more like a planned bank/train/armored-truck heist than the more traditional "attack of opportunity" present in most bandit encounters. This is why I mentioned the concept of raiders or other groups acting on specific orders for some other purpose. A group of NPCs attacking an adventuring party should never be a spur of the moment thing (well, not if they want to succeed), but a planned attack, often not just "because we want their stuff" but because some other powerful wealthy person has hired them to do this (even if it's not the PCs specifically, but "kill any people in this area who might become a threat to me" type orders). Or they are defending their territory maybe.

Actual on the fly bandit attacks on a group of PCs should almost always be presented as a monumental mistake by the bandits. Either the party has taken some steps to disquise their nature (my table quite often uses the "pretend to be a merchant with some guards" bit when traveling around), or actually are relatively low level, or the bandits have just completely failed their "spot easy money" skill roll.

The problem is really one of scale. The power level required to even have a chance of successfully taking on a decently experienced adventuring party is so great, that the same group would be vastly better of using their own skills and abilities doing something other than hanging out along the side of road waiting for random people to come by to rob them (again, folks specifically being paid/ordered/forced-by-their-dark-lord to interdict some area for some other reason excepted). But I have actually seen GMs try to do this. I distinctly recall one GM who really really wanted us to have trouble dealing with some group of NPC bandits in the area we were travelling thorugh, but we were running a really powerful group. So he just kept ratcheting up the power level of the bandits we ran into, to the point of absurdity. At the point where your bandits are wielding sufficient force to tople most small to mid sized kingdoms, you have to wonder what the heck they are actually doing there in the first place.

EDIT. Adding this bit as well:

Consider otherwise, a merchant is guaranteed to have commodities and liquidity. A travelling noble you can ransom for a fortune to make it worth the risk.

More to the point, the very fact that the merchant has goods on wagons and is traveling somewhere with them means that the goods are expected to be in-demand and sellable at the destiation the merchant is heading for (or may even be a consignment and payment is waiting upon delivery). The point is that the odds are nearly 100% that "someone just down the road" is wiling/able to turn those goods into cash for whomever shows up with them. If it wasn't, then the merchant would not have had those goods on those wagons and been heading in that direction in the first place (or, I suppose, the merchant is just really bad at merchanting).

Assuming said bandits have any contacts at all in nearby cities/towns to offload their stolen goods (and why wouldn't they?), it's a pretty much guaranteed/fast turn around profit for them. The goods get to where there is demand for them, but just travel through different hands along the way. I suppose we could imagine some form of bandits who hang out deep in out of the way places, living off the land and whatever they steal from people who pass by, but IMO that's leaning more into the "we're protecting an area we live in and control" than traditional banditry.

Similar point about ransoms. I tend to think of NPCs in these sorts of professions as part of a larger whole. The bandits don't do everything themselves. They do their part "waylay travellers on the road", and then use contacts elsewhere to deal with what they get. So in this case, the bandits are probably not going to be the ones managing the ransom at all. They happen upon some valuable people to kidnap, sell them to some group in town with the contacts and resources to handle kidnapping and randoms, pocket their cash and move on. That other group then puts out the ransom demands because that's the part of the criminal spectrum that they are good at.

Subtle little aspects of how NPCs behave in a game world can go a long way to making that world feel more real to the players. And sure, we might think that "going after the bandits and getting the kidnap victims back" may make for a satisfying story, but "finding out that the prisoners have been moved to a nearby town, where the notorious <insert evil org name here> gang have taken them and are demanding X gold pieces, and now you've got to deal with these guys, and along the way maybe find other criminal activities and prisoners to be freed" IMO makes for an even better gaming experience and allows for a much deeper and more detailed (and easy to put new story hooks into) setting. Dealing with an isolated group of bandits is just dealing with a single group. When those bandits are just one cog in a larger wheel of crime and "evil things" going on in the world around you, that creates the opportunity for depth.

[Duff]

Bandits forced to desperation by social injustice or disaster.
"It's the only way we could feed our children..."

Bandits who can be recruited to a good cause (EG the Ronan from Servant of the Empire)

Bandits who have been cursed to live as bandits. Or think they have

[Gnoman]

More to the point, the very fact that the merchant has goods on wagons and is traveling somewhere with them means that the goods are expected to be in-demand and sellable at the destiation the merchant is heading for (or may even be a consignment and payment is waiting upon delivery). The point is that the odds are nearly 100% that "someone just down the road" is wiling/able to turn those goods into cash for whomever shows up with them. If it wasn't, then the merchant would not have had those goods on those wagons and been heading in that direction in the first place (or, I suppose, the merchant is just really bad at merchanting).

Assuming said bandits have any contacts at all in nearby cities/towns to offload their stolen goods (and why wouldn't they?), it's a pretty much guaranteed/fast turn around profit for them. The goods get to where there is demand for them, but just travel through different hands along the way. I suppose we could imagine some form of bandits who hang out deep in out of the way places, living off the land and whatever they steal from people who pass by, but IMO that's leaning more into the "we're protecting an area we live in and control" than traditional banditry.

Historically, fencing bulk goods has never been as easy as this, to the point that even legitimate privateers (who have a license to steal from a government, and thus don't face nearly as many obstacles as outright pirates) would often not bother to keep such a cargo unless the ship it was on was valuable in and of itself - separating out the crew needed to man it was considered a greater problem than any profit it would bring.

The same is true of pirates of the land, aka bandits. Taking a merchant caravan needs a lot of manpower to handle the cargo, and that very cargo will slow your movements. If anybody escapes to raise an alarm, trying to hold onto that cargo will make you an easy target for pursuit even if you have enough guys to drive the wagons and capture/provide enough animals to tow them.

Then you run into the issue of actually disposing of it. As a rule, townspeople do not like bandits. If you just stroll into town with your stolen goods, and somebody happens to realize that you did, in fact, steal it, they're likely to raise the militia against you because your very existence is a threat to their lives and property. So either you have a specific patron that can "launder" the goods, or you divide it into small packets and sell it "retail" to avoid raising a fuss. Both have enormous time costs.

Meanwhile, in your typical fantasy world having some guy show up with some fancy weapons and slightly damaged fancy armor is Tuesday.

[Duff]

Bandits at various points on a continuum with other groups:
Freedom fighters
Cultists
Mercenaries
Refugees
Tax collectors
Smugglers
Locals of a different cultural group ( tribe, species, people, nation, clan etc)

[gbaji]

Historically, fencing bulk goods has never been as easy as this, to the point that even legitimate privateers (who have a license to steal from a government, and thus don't face nearly as many obstacles as outright pirates) would often not bother to keep such a cargo unless the ship it was on was valuable in and of itself - separating out the crew needed to man it was considered a greater problem than any profit it would bring.

The same is true of pirates of the land, aka bandits. Taking a merchant caravan needs a lot of manpower to handle the cargo, and that very cargo will slow your movements. If anybody escapes to raise an alarm, trying to hold onto that cargo will make you an easy target for pursuit even if you have enough guys to drive the wagons and capture/provide enough animals to tow them.

Well, sure. You'd focus on higher value cargo. You leave the bags of grain on the wagon, and take the box of gemstones, for example. Or the money box. Rare textiles? Silks? Spices? All could well be considered worth the effort of carting off.

Then you run into the issue of actually disposing of it. As a rule, townspeople do not like bandits. If you just stroll into town with your stolen goods, and somebody happens to realize that you did, in fact, steal it, they're likely to raise the militia against you because your very existence is a threat to their lives and property. So either you have a specific patron that can "launder" the goods, or you divide it into small packets and sell it "retail" to avoid raising a fuss. Both have enormous time costs.

Yeah. This is why I tend to assume that if there are bandits operating outside some decent sized town/city and along a reasonably well travelled road, that they would almost certainly have to have contacts in said city/town specifically to manage the goods they steal. Bandits will not long operate if they have to physically carry the goods they steal into town and then try to sell it themselves. But... if they know a guy who already handles smuggled and/or black market goods, then it's an easy matter to sell it to that guy instead. The middleman involved makes this slightly less profitable per haul, but makes for much faster turnaround of the goods that are stolen.

And sure, we can just run bandits as "folks in the hills stealling stuff for their own use/sale" if we want. And that's perfectly legitimate. But I find the the whole "bandits on the road have contacts in town who sell stuff for them" to make for a much more interesting set up from an adventuring point of view. Now, the bandits aren't just an isolated encounter, but become a hook that leads to other things as well. And that can lead to yet more things: Does that smuggler only deal in goods brought in by the bandits, or get stuff from other sources as well? Is that smuggler/fence operating as an isolated thing, or is that part of a larger set of criminal operations in said town/city? Lots of potential here that can spin off from a simple "there are bandits here" starting point.

Meanwhile, in your typical fantasy world having some guy show up with some fancy weapons and slightly damaged fancy armor is Tuesday.

Eh. Maybe. I guess this depends on how vigorous the purchase/sale of magical weapons and armor is in the setting. In the game setting I play in, magic weapons and armor are super rare items and their owners aren't likely letting go of them (while still alive). So someone showing up wanting to sell stuff like that is going to garner far far more attention and suspiciion than the same person showing up with a box of finely cut gems, or some exotic spices, or whatever.

Also, at least in the setting(s) I tend to run, sales of such things are quite slow. They are expensive. Very few people are walking around with the kind of cash needed to buy them. So very specialty items, that move very slowly. It's like stealing rare art. You'd need more/better contacts to sell that stuff than you'd need to sell more normal goods.

I'm not at all a fan of the "magic mart' in games I run. So that may certainly color my perception of "Bandits can just kill the party and take their stuff and sell it". The bandits, if they could take the party out, would likely keep their stuff and use it for themselves. Of course, if they are powerful enough to take out the party in the first place, I really have to question if they qualifiy as "bandits" anymore. But that's a matter of definition I guess.

[Jay R]

I'm about to run a bandit encounter in the middle of a civil war. The bandits had been an army unit until they realized that they weren't getting the profits from their raids.

I assume that if bandits occasionally show up at the army camp with extra food and weapons to sell, the commander will buy them, without worrying too much where they came from. [And may even be more supportive if the goods had originally been intended for the enemy.]

If the goods were originally bound for this army, the quartermaster may not know (or even care) who was supposed to make the delivery.

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In most D&D worlds I've created, the earlier civilization is breaking down, or has already broken down. There has to be a reason why a small group pf adventurers is dealing with the problem, instead of the soldiers and bureaucrats. Dungeons with treasure abandoned in the wilderness imply that a larger civilization had been established there before, and then fell apart.

In Tolkien, Khazad-dum and the Greenwood had been flourishing places before they fell, and became Moria and Mirkwood. Jonny Quest and company often explored ruins. Tarzan found the degraded remains of the fallen empire of Opar. Indiana Jones researched lost treasures of fallen civilizations.

In this kind of environment, bandits can prosper.