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This question is really more of a tactics and plotting question than a rules question. In D&D 5e, a creature can avoid opportunity attacks when running away by using the Disengage action (although some features allow opportunity attacks in spite of this).

While DMing combat encounters I have found that by the time I think a creature might want to flee, there is usually a really strong chance that the players will drop the creature anyway. But fleeing earlier seems absurd or anticlimactic, like the creature runs at the first sign of blood. It's widely discussed in optimization that D&D 5e combats tend to finish in about 3 rounds. If the characters are knocking out ⅓ or more of a creatures hit points each round, the combat looks like this:

  1. Creature reduced to ⅔ of their maximum hit points.
  2. Creature reduced to ⅓ of their maximum hit points. Creature decides to flee.
  3. Creature flees using Disengage or Dash:
    1. Creature takes Disengage action and runs 30 feet. Characters run 30 feet and kill the creature.
    2. Creature takes the Dash action. Characters get opportunity attacks and kill the creature.

Modules are often written with notes on when creatures will flee. For a group of lower CR creatures (relative to the party), a module might say "If more than half their number are killed the remaining orcs will run away." It's usually not problematic if a handful of the fleeing orcs die. For a single creature that is a medium or hard encounter, a module might say "If the frost giant loses more than half their hit points, they will run away." If the players do enough damage to the fleeing frost giant to kill it, whether that is a problem depends on the frost giant's role in the plot.

The problem really comes when it is a single creature who needs to survive for plot reasons.

There are several features that could allow a creature to flee safely. Various teleportation abilities (teleport, but also short range teleports like misty step or dimension door) will allow the creature to completely vanish or at least allow movement to a safe distance from which to run away. Special movement rates such as flying, swimming, or climbing can help, so long as the characters don't also have that movement ability. The problem primarily would arise for a terrestrial, non-magical creature who needs to run away on foot. (But, certainly, if some or most of the party have a flying or swimming speed, as may be the case with high-level parties or unusual character races, the problem transfers.)

On the one hand, the obvious solution is "Give the creature a feature that allows them to flee successfully." This could be a potion of flying if they can't usually fly, say that they have the equivalent of the rogue's Cunning Action feature so they can Disengage and Dash in the same turn, give them a magical whatsit that allows them to dimension door, etc. The problem with this solution is really character annoyance at seemingly arbitrary abilities that exist transparently to allow creatures to escape. Giving the creature allies or minions who could help with the getaway may also be plot-breaking, if, for example, the adversary is supposed to be a loner.

Basically, how do you save the goblin king when the goblin king is just a goblin with an unusually large pool of hit points?

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    \$\begingroup\$ I wish I had an answer. My table has been chewing on this question for years. It's perhaps the single most unsatisfying part of 5E combat for us. There needs to be a "fighting retreat" or "yielding ground" option, and there just isn't. Historically, the worst wartime losses came when the losing side broke ranks and the battle became a rout. And 5E opportunity attacks model that well. But when the retreat is disciplined, orderly? No options. Barring special abilities, at best you disengage and move only to have the enemy follow you on its turn, leaving you no better off than you were. \$\endgroup\$
    – screamline
    Nov 16 at 16:44
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    \$\begingroup\$ The need for homebrew should be justified, e.g. to really answer the question it should be made clear that RAW can't answer it. Once you get to homebrew, there is no "right" answer. But an example of a homebrew solution would be acceptable. \$\endgroup\$ Nov 16 at 16:58
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    \$\begingroup\$ While 5e combats typically last around three rounds, unless your party is heavy with AoE casters, this does not typically take the form of each enemy having a third of its hp reduced each round. Rather, players will typically 'focus fire' to drop a third of the enemy individuals completely each round, and leave the others untouched. \$\endgroup\$
    – Kirt
    Nov 16 at 17:53
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    \$\begingroup\$ @Slagmoth I think Dodge is no more meaningful a withdrawal option than Disengage. Opting for one over the other just moves the odds around -- the defender disengages and takes n attacks without disadvantage, or dodges and takes n + 1 attacks with disadvantage (and that's assuming there's only 1 attacker). The end result is the same: the defender does nothing but move and defend themselves, the attacker moves right along with them and still gets to attack, and the start of the next round looks exactly like the start of the last one, except 30 feet away. \$\endgroup\$
    – screamline
    Nov 16 at 21:11
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    \$\begingroup\$ Arguably this whole issue (getting free attacks on fleeing creatures) is an error baked into D&D from the outset (1974) by virtue of porting over the rule from Chainmail mass combat that a routed unit spends a turn in confusion, represented by standing still with its back to the enemy. Some of us house-rule that error back out. deltasdnd.blogspot.com/2018/08/on-free-retreat-attacks.html \$\endgroup\$ Nov 17 at 14:22
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You're correct that the rules kinda stink for this.

The rules for combat, that is. But at my tables...

Fleeing is not fighting.

The movement rules for combat are inherently predicated on the notion that combatants are trying to engage in combat. And you've correctly pointed out: combat-movement doesn't really afford a way for a creature to leave melee without likely eating an attack every round. (It's just a question of where that attack happens!)

What we need is a way to treat not the tactical maneuvering and positioning of combat, but something that tackles trying to get the hell out of Dodge....

Fleeing initiates a chase.

The Dungeon Master's Guide has rules for chases (DMG p.252). They're surprisingly good, and for all of 5e I've used them to take over, immediately, when one party to a combat flips that switch from "beat them" to "beat feet!" It's not danger-free, not a guaranteed "pass" for the creature trying to escape, but it's quick and gives them a chance that they don't have within combat-movement and nicely (IMO) switches up the pace of the session.

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    \$\begingroup\$ I remember a discussion I had with doppel about how she felt that the chase rule ought to have been in the Basic DM rules when the game came out. Given how often I've used them as DM, and the fun we had when we played them when you were DM, maybe they should have been core. \$\endgroup\$ Nov 16 at 17:23
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    \$\begingroup\$ @KorvinStarmast that, along with a two-liner in the PHB's combat chapter on "fleeing" would be a game changer for many tables, methinks. Perhaps it'll make it into 5.5e? <ducks thrown objects> \$\endgroup\$
    – nitsua60
    Nov 16 at 18:39
  • \$\begingroup\$ Careful. This opens the door for the PCs to flee from the BBEG themselves, reducing the threat by a major amount \$\endgroup\$
    – tuskiomi
    Nov 16 at 18:49
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    \$\begingroup\$ I have found myself perfectly happy every time PCs have fled from a BBEG. The BBEG continues pursuing their own goals, now with lots of firsthand knowledge of the PCs and some extra motivation to bring the fight to them =) \$\endgroup\$
    – nitsua60
    Nov 16 at 18:53
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    \$\begingroup\$ and their little dog too! \$\endgroup\$ Nov 16 at 20:21
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If a creature must escape or live for plot reasons, the DM makes them auto-escape

As you've laid out, fleeing from combat in a combat encounter is nearly unmanageable, but there are ways around this (see below). The real issue is that you have an NPC that isn't allowed to die/be captured and this cannot be solved in mechanics. A creature could be Entangled, die before its turn to use a Magic Escape potion, etc.

It is ok to tell your players they defeat a creature, and it runs off into the sunset. If you're homebrewing or building your own campaign, I'd recommend not requiring NPCs to live as players are smart and will immediately kill that random barmaid they met who is secretly the BBEG, but if you're running a module or can't avoid that-- just narrate their escape, reward the players XP (if appropriate) for winning the encounter.

That being said, if you want a better system for fleeing enemies, where the party should have a chance to catch them. . .

If all of the enemies are fleeing, you're no longer in combat-- use the Chase rules.

Recall what the combat rules say:

Beginning of a combat encounter, when everyone rolls Initiative. Once everyone has taken a turn, the fight continues to the next round if neither side has defeated the other.

An enemy choosing to flee is a defeated creature and, as you note, fleeing doesn't work well within the combat encounter rules.

This is why you probably shouldn't use combat rules once all enemy creatures have decided to flee-- you should instead consider the Chase Rules (Dungeon Master's Guide Chapter 8, Pg 252). It contains rules for dashing, opportunity attacks, stealth and casting spells and allows a lone goblin (king) to have a real potential for escape.

That being said once you get past level 3 or so, there are enough spells that limit movement or just restrain (Web, Entangle, even Earth Tremor), that if the players are willing to use the resources, enemies without having ways to get around that don't have great odds of escape.

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I think you are having several interconnected problems. Here are some solutions.

Beware of trying to script the game

D&D is a game where you discover what happens by playing. You've written in your notebook "and then the bbeg escapes to fight another day!" But your players aren't actors following a script, they are just trying to kill this evil enemy. This is a fundamental mismatch about what your game is.

Make combat harder

To put it bluntly, the monsters you are fielding are too weak. If players deal a third of the monster's hp each turn, then the monster flees on turn 3, it will practically always die. The solution is simply to use stronger monsters and have them flee earlier.

This is an extremely common problem, especially in games where enemies do not flee. I have seen this come up countless times, you are definitely not alone here.

Make sure combat is part of a larger interaction

The way you frame combat is as if it's a minigame. I don't think this is the correct way to think about combat. Combat happens when two parties cannot settle their disagreement and so the conflict escalates. Before combat happens there should be some interaction which leads to combat, and as one side feels they are losing they should attempt to deescalate.

At the start of combat each side has something they want, very rarely should both sides want to simply kill the other side. When the party enter the Goblin King's lair, they want to slay him, but what does the Goblin King want? To survive. When the party fight a pack of wolves, what do the wolves want? To get some food. What do bandits want when they ambush travelers? Things to sell for money. It doesn't serve anyone's goals to fight to the death - or perhaps even fight at all.

Add more complexity to combat

If your combat is all about dealing damage, then I think you can likely increase the complexity. I like to think about two major things; time and space. What will happen as the fight goes on: Are reinforcements being called for, is the lava surging, is the floor collapsing? And what is the environment like: is it scattered with debris, are there trees and bushes, have traps been set? Ideally I would like both parties to have a tactical environmental goal to compete over, and something to interact with. Even putting a door between two rooms means that someone can run through the door then turn around and bar it or hold it closed.

Make combat more multidimensional

All too often DMs create villains that are evil and exist to be killed. You don't have to do that, you can make the situation less cut and dry. Perhaps the Goblin King is in cahoots with the human King, killing the Goblin King would be a bad move politically, and could make the party wanted. Perhaps the Goblin King is fighting something deep underground, making killing them a risky choice. Perhaps the townsfolk blame the party for the mysterious disappearances, and don't believe the Goblin King is real - the party's name can be cleared if they bring the Goblin King alive for interrogation.

Remember fleeing isn't just about running away

Many creatures have abilities, features, spells, can take actions, or manipulate the terrain to aid their escape. Throw down AOE or control spells, use disengage, use hide, dash, run across the log spanning the ravine then kick it down, close doors, ready actions, etc. There's more you can do than just running away.

How I would run the Goblin King

Firstly, where is the Goblin King's throne room? It's in an underground burrow. There's a throne of trash on a platform surrounded by various traps. On the side of the room is a gong that is used to call for reinforcements from the various tunnels that surround the room. What does the Goblin King want? Mainly he wants to survive, but he also doesn't want to lose face.

As soon as the fight starts, the Goblin King will start bashing the gong, causing goblins to start coming to his aid. The party would do well to separate him from the gong, or they will be overwhelmed. If the party get the king away from the gong or hurt him down to half health, he will flee, trying to get to one of the tunnels. If he can, then the chase is on and the party will have to follow.

If the players kill the Goblin King, then the Goblin King is dead. Players aren't going to follow your script, and neither should you script in the first place. Rather than a story about a recurring Goblin King, now you have to think what the goblin tribe will do - perhaps another king will rise.

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    \$\begingroup\$ Yeah, that last part: the OP says not all BigBads have minions, but then gives an example of a goblin king, who is defined as having lots of minions. You don't even need a gong. Along with the palace goblin-guards he can have 2 bodyguards who's job is to stay back and hold-off pursuers when the king flees. \$\endgroup\$ Nov 17 at 3:33
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    \$\begingroup\$ RE "You are writing a script" - this is always a trap many GMs fall into. Here is a simple litmus test: 1. Is there something you require to happen? 2. Would a dice roll possibly prevent it from happening? If the answer is "Yes" to both, then you've introduced a script element in your game. E.g., you require the villain to show up later again but a combat (dice rolls) kills them. If any piece of plot also has any dice rolls associated with it, then it should be in some way optional. Or don't bring dice to it. \$\endgroup\$
    – VLAZ
    Nov 17 at 20:54
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You actually have three options instead of the one.

1. Give the villain a guaranteed escape mechanism. This is what you're asking about. The exact mechanism is not important — it can be a plot device, a clever use of the rules or just a DM's fiat. The point stays the same — you trick the players into believing they can kill the villain, but actually they can't. This can be very frustrating, so I advice against this option.

2. Let the players have their agency. If players want to chase and kill the goblin king, and the DM gave them reasons to think they can do this, at least they should have a chance. The complicated part is, the game should remain playable if they succeed. This approach is preferable for sandboxes but works poorly for plot-oriented games.

3. Be honest with the players. Have a recurring villain who doesn't risk his life (for now). This is very different from the first option. "The king is unreachable, you can not just kill him, at least for now" the players see. Now they can make informed decisions and anticipate the consequences. See How do I add a recurring fantasy villain without frustrating the players?

Meaningful combat could also help. I strongly recommend "The Angry Guide to Kickass Combats" series for this topic. When each combat has its goal, fleeing enemies become a valuable option instead of an annoying nuisance.

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    \$\begingroup\$ You really have to be careful with option 1... like really careful. I am not a fan of +3 Adamantine Plot Armor of Invulnerability. I have been in games where the DM miscalculated our ability to use tactics and just waved his hand to let the "Plot" device get away. It will sow distrust in you as a DM with your players if this is a recurring thing and potentially you will lose them especially if they feel, as I did that their actions didn't matter in any respect at certain points. \$\endgroup\$
    – Slagmoth
    Nov 16 at 19:07
  • \$\begingroup\$ For number 1, I always just make sure the villain has a Contingency spell set up, usually with Teleport or something similar. \$\endgroup\$
    – Michael W.
    Nov 18 at 20:56
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Legendary actions are your friends

Firstly, I would note that a creature that needs to survive "for plot reasons" shouldn't be anywhere near hitting distance of a PC party, ever. The best-laid plans of DMs on "how to make my BBEG survive" have about a 70% rate of failure in my experience. (Illusions, simulacra, and if all else fails, good old True Resurrection can be helpful in these circumstances, however.)

That having been said, if your villain is important enough that they have to survive, they're probably important enough to be considered a legendary creature, and therefore have legendary actions, which can be used to enable escapes. The vampire has an excellent example in their "Move" legendary action, which allows them to move up to 30 ft. without triggering opportunity attacks, up to three times each round. Whether you're custom-building your villain or using an existing monster stat block, there's nothing that prevents you from adding some legendary options to make them more of an epic encounter.

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  • \$\begingroup\$ Resurrection is great, as can be seen by Matt Mercer's Lady Briarwood, servant of Vecna \$\endgroup\$
    – Carson
    Nov 18 at 21:40
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Any NPC that thinks they might need to flee should be prepared to.

For example, Caltrops are very effective at stopping PC movement. Any NPC carrying a bag of them could simply empty them out of a handy sack as they run (note the DMG says that caltrops take an action to spread, but also says that dropping items is a free action, so there's seemingly a lot of leeway here). Depending on how big that big of caltrops is, the PCs may need to succeed on 6x DC15 dex checks (though this is very overkill), each failure reducing their movement by 10 feet until they regain 1 hitpoint. Note that RAW, a creature which is dashing and fails this check actually loses 20 movement, as caltrops reduce walking speed, and dashing simply gives the character an extra set of walking speed.

A more widely used example may be ball bearings. They function in the exact same way, except they don't do damage, have a lower DC, and simply make the creature fall prone.

And then of course the evil thing to do would be to give the creature a mixed bag of both... But no DM is that evil, right?

There are many more useful items that any creature may carry on their person which would give them the edge when running away, it's all a matter of planning ahead. It's as the old addage says, failing to plan is planning to fail.

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    \$\begingroup\$ Dropping a bag of caltrops won't do much, that's just a bag on th floor. Spreading the caltrops themselves is what causes the difficult movement, and isn't really open to interpretation. But planning for an escape is certainly something that any self respecting bbeg should do. \$\endgroup\$
    – SeriousBri
    Nov 16 at 19:56
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    \$\begingroup\$ @SeriousBri Maybe, we're not dropping anything at all, but merely opening the drawstring on the already held bag. In which case, no dropping is being done by any character. Maybe, the bag is held closed by a string, which the BBEG must hold, and if let go, the bag will open by it's own. There are TONS of ways to spread items without manually taking the time to do a series of steps, and many ways which don't require a lot of thinking on the NPC's end. \$\endgroup\$
    – tuskiomi
    Nov 16 at 20:25
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    \$\begingroup\$ Adding a few other ways an intelligent villainy can plan for escape would improve this alot. trap doors, or doors with no latch on this side, narrow passageways full of minions, turns the block line of sight followed by forks, grease, braziers that can e tipped over, the options are endless. , \$\endgroup\$
    – John
    Nov 18 at 0:28
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Knock the melee fighters prone and run away

Plenty of monsters have an ability to knock multiple adventurers prone at a time, without using an action. These include the aboleth, demilich, the adult blue dracolich, the ancient and adult black dragon, and probably quite a few more.

For example, here’s approximately how a demilich's escape could go1:

  • Knock adventurers next to them prone using a lair action
  • Take the Disengage action
  • Fly 30 feet away, to a place behind full cover (e.g. around a corner)
  • Flick some switch or press some button (using a free object interaction) that causes the pathway they used to be blocked.2

Of course, if your party has a spell prepared that allows them to go through walls and the like, they could be blocked by magic-resistant walls.

You can give other monsters similar powers (limited them to one or twice a day to not unbalance the monsters), and increase the amount of monsters who escape that way. Of course, don’t overdo it. If a triceratops with an Intelligence score of 2 does this, your players will probably get annoyed.


1 This requires the demilich to be right after the lair actions in terms of initiative order, but you can easily homebrew that to allow the demilich to either delay one of their lair actions to right before their turn, or give them a power that they can use a lair action right before their turn once a day (which, seeing as how demiliches are smart, they’d save for when they need to make an escape). There’s also the problem of there only being a 50% chance of only getting the lair action half the time, but you can homebrew that away to allow them to get a guaranteed use once a day.

2 Of course, make sure you describe the place appropriately. If you describe it as a wide open desert before you do this, It’ll probably feel like you are excessively railroading them. If you describe it as a mysterious temple with hundreds of corridors, your party likely won’t be surprised when the Demilich goes down a corridor, and when the temple acts mysterious and has anti-magic walls.

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    \$\begingroup\$ Having a button appear that wasn't there before is a sure fire way to lose the trust of players, so are magic resisting walls and other 'sucks to be you' moments \$\endgroup\$
    – SeriousBri
    Nov 16 at 19:57
  • \$\begingroup\$ @SeriousBri that depends how you describe the place. If you describe it as a mysterious temple with large amounts of trapped passageways, of the demilich goes down a passageway, and the terrain acts unusual, it won’t be surprising. \$\endgroup\$ Nov 16 at 20:15
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    \$\begingroup\$ I think that is a key element to your answer which is missing, because it changes your answer from 'retrospectively make something up' to 'build a believable world' - at least how I read it, and one is awesome, one is not. \$\endgroup\$
    – SeriousBri
    Nov 16 at 21:55
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    \$\begingroup\$ @SeriousBri updated. \$\endgroup\$ Nov 17 at 14:40
  • \$\begingroup\$ What is the advantage of knocking them prone if you will disengage and block the pathway anyways? \$\endgroup\$
    – RHS
    Nov 18 at 11:35
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A creature should not be fleeing based solely on its current hit points, it should flee when it realises that it is not going to win. That calculation includes not just its hit points but its other defensive and offensive abilities. In the case of intelligent creatures, that may well include minions or even tricks and traps set up to prevent the party ever getting far enough to encounter the creature. Just as you might describe a creature as being "wounded" or "badly wounded" to the players, the potentially fleeing creature will make an assessment of the characters and balance that against its own, currently available, abilities.

A creature that knows you just killed its followers in the next room seeing you enter unscathed might flee right there and then, unless it has some big hitting ability. If that big hitting ability is ineffective or 1/day then it will cut and run.

ESCAPE PLAN

There are other ways to resolve the problem than just running away, as well as escape plans mentioned here by others, off the top of my head there are...

  1. Ransom- the opponent throws up his hands and shouts out some offer the PCs can't refuse (My father will pay 1,000GP for my safe return!, I know where the treasure is!, etc.)
  2. Stand off- the opponent grabs a lever and yells "if I pull this the roof caves in!" or similar.
  3. Surrender- opponent just plain stops fighting ("Take me in", directed at the PC with the LN/LG deity symbol on display).

WORST CASE So your plot essential baddie dies, bring them back as a ghost, resurrect them, etc. How about instead of fleeing they say something like "“If you strike me down, I shall become more powerful than you can possibly imagine.”

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