‘Supposed-to-lose’ fights have been a staple of games for as long as I’ve been playing them. If done well they allow the players to experience the desperation of a last stand, or hammer home the fact that their foe is operating on a different level to them – for now, at least.

However, when it comes to including them in tabletop RPGs you can begin to run into trouble very quickly. Simply put, PCs aren’t very good at losing.

Of course, I don’t just mean that some of them take it badly – after all, every time you roll a dice you should be prepared to accept the chance of failure. Rather, I mean that over the years I’ve found that that inventive players are very, very good at getting out of seemingly impossible situations.

The excellent Merric Blackman covered some aspects of this in a blog a little while ago, where he pointed out that problems with having a story that relies on the adventurers getting captured, and many of the same points apply here.

Simply put, forcing your players to do something against their will takes away their agency and therefore their investment in your world. This only becomes worse when you force them into a situation where they have to fail.

Running Out of Options

One of the first issues of ‘supposed-to-lose’ fights is that it’s hard to get the adventurers to stick around long enough to actually lose.

For example, when the game wants to make sure Beatrice whips your ass in Final Fantasy IX  it just disables your ability to flee. In D&D the only way to do this is to make sure the battle is set somewhere specially designed to stop anybody escaping, such as a magical prison that cancels out teleportation and plane-shift spells.

This often feels incredibly contrived, and even then you need to worry about Wizards using Passwall or Fly, Druids wild-shaping into eagles or Rogues simple sticking on their climbing gloves and scaling shear walls.

Battles like this can be used to teach the PCs that sometimes running away is the most sensible option, but when you’re a new DM it can be easy to fall into the trap of over-planning. Crudely forcing a scene where the villain gloats over the fallen party or tosses them in the jail cell where they meet a plot-vital NPC doesn’t make them appreciate that the world is dangerous, but rather that the DM can force them into situations against their will.

Even if you don’t mind the adventurers running away from a battle, simply sticking an invincible enemy in front of them can cause problems. One of the enjoyable things about D&D is the fact that, for the most part, the enemies have to follow the same rules as you do. When they obviously break this it gets extremely frustrating.

Some time ago I played in a public campaign where the villain made an appearance in an early session with the aim of kicking us around for a while. However, a mixture of good teamwork and lucky rolls meant that we held up surprisingly well against the Drow Warlord and her Wyvern mount. This didn’t matter though, because the DM clearly wasn’t tracking any damage or even bothering to give the enemies consistent stats.

We were meant to lose, and there was nothing we could do about it. What should have been an exciting showdown against the odds became a waste of time that left us bored rather than thrilled.

Beating the Odds

Does this mean that you should never allow the adventurers to get themselves into a position where they might lose? Of course not!

If they choose to attack the king while he’s surrounded by his cadre of elite guards then they’re virtually guaranteed to get themselves beaten down, no matter how well they roll.

Likewise, there’s nothing wrong with having the party confronted with a late-game villain while they’re still struggling against Goblins and Kobolds. Few things build a grudge quite as well as having the Lich Disintegrate your second-level Cleric and then teleport away while laughing.

But neither of these force the adventurers to do anything, and the plot doesn’t rely on them being defeated. The battle is there as a challenge, not as a glorified cut-scene. That difference may be minor – after all, the outcome is likely to be exactly the same – but it really does make a difference.

Here are a couple of things you should have in mind to make a good encounter with an overpowered enemy:

1. Don’t have your entire plot hinging on the PCs getting wiped out. There is almost nothing that can’t be achieved by a sufficiently inventive (and lucky) player, especially as they get access to higher-level abilities and items.
2. Don’t take away player agency. Nothing kicks you out of your immersion like having all your efforts slapped down by DM fiat. If they pull out something inventive and inventive they should be rewarded, not punished.
3. Don’t have an enemy obviously cheat. If the adventurers literally can’t do anything against an enemy then you shouldn’t be having them roll in the first place. A party of level one characters won’t be able to do much against an Ancient Red Dragon, but if they land a couple of critical hits and manage to wound the beast they’ll remember the fight forever.