As much as D&D is story based around game play, the fact it is a game and not a story means there are times when the tale goes awry. The protagonists fail and fail hard when everything leading up to the moment says they should have succeeded.

Having played in games where this has happened to my character and having DM’d sessions where this happened to my players, I can tell you my point of view on how to handle these moments have evolved.

Early on, I was all for the position that it is a game and bad things happen, suck it up buttercup. This was not an extreme position to take when we’d be playing these games every week and changing characters with every new supplement that was published.

Then I became story obsessed and became invested in my players’ characters. I didn’t want any character to die. This removed the feeling of threat from the game. Was it fun? Yes. Did the players get a sense of “winning”? No. They knew it was rigged in their favor and exploited it to the best of their ability.

My dilemma was how to thread this needle. Keep the idea of a threat, but not be cavalier in the treatment of characters in the story being told. How best to treat character failures in the game as part of the greater story? What would Star Wars have looked like if Luke, Leia, Han, and Chewbacca were killed in a trash compactor? Or what if in Indiana Jones and the Lost Ark, Indy drowns on the submarine?

The truth of these moments is they are built into the story of these movies. They are moments the writer planned and are part of a story arc. In D&D you can plan those moments as well. They are adventures that are essentially The Empire Strikes Back. The player characters can succeed but the story is still a bummer because forces bigger and more powerful than the characters succeed at a goal.

What normally happens in D&D is a very normal adventure where the characters skills are balanced against the encounters goes awry.

The dice hate your players and they’ve been rolling like crap all game. Their intricate plan of attack against the evil Wizard Warlord of Dellakin has fallen apart because the normally perfectly stealthy rogue triggered a Glyph of Warding trap and the normally ‘can’t miss’ Ranger botched her Advantage rolls.

Meanwhile no one perceived the Lurker which has successfully incapacitated the Paladin. The “henchfoes” of the miniboss, the cruel Lieutenant Verrot Stihm, haven’t even made an appearance yet.

These are the moments when luck has turned against the players and no amount of fudging dice rolls will rebalance the encounter. Everything sucks. What do you do? What can you do? Do you just chalk it up to a bad session and hope to recover the next game? Do you send you players home feeling like losers because the dice betrayed them?

In D&D terms this can become a TPK (total party kill). This is when all the characters are killed and everything comes to a grinding halt. Honestly, I’ve only been part of one TPK and that was when the entire party failed to answer a riddle while trying to assemble a wand of Orcus. The game was fun right up to that moment and then it sucked.

It wasn’t the DM’s fault (though it gave me a hatred of riddles in games where my smart character is hindered by my real stupidity). We were screwed by an obstacle that we were capable of conquering. We simply failed. Four characters were now frozen in an energy field and the game came to an end.

What is the End of the 2nd Act? “All is Lost moment”

Let’s pause for a moment and talk about storytelling and the 3-Act Structure. This structure was discussed by Aristotle in the Poetics and is as simple as a story is composed of a Beginning, a Middle, and an End.Obviously I’m bringing this up because there is more to it than something that simple. The three act structure helps build the story. The First Act introduces us to the characters, the world, and being the inciting incident.

In D&D campaign terms, the First Act is really all the adventure up to the introduction of the Big Bad. The Inciting Incident is usually when something the Big Bad does alters the fortunes of the characters. It puts them in peril or in some other way makes the bigger conflict personal. Life for the characters will never be the same and their actions will have an impact on the world defined before the Inciting Incident.

The Second Act is about the Rising Action. Most of the campaign is spent right here. The adventures move away from clearing rats from the cellar of the local tavern to destroying the temple dedicated to the Mad God. The actions have more meaning to the world as a whole. Then something happens. It is sometimes called the “All is Lost Moment“. Most stories have this moment.

In Star Wars just as Luke, Leia, Han, Chewbacca, and Obi Wan are about to escape the Death Star, Darth Vader shows up, duels Obi Wan, and “wins”. The death of Obi-Wan, the person Princess Leia was searching for to help the rebellion, seems to be a heavy blow to the plans of everyone involved in the galactic conflict. Uniting Obi-Wan and Princess Leia was the whole point of the movie up to that moment. Truly, how could they recover and what does this loss mean for the Rebellion? Tragedy is assured.


In Superman the Movie, Superman fails to save Lois Lane as he tried to stop the two missiles. He is able to stop one of them, but one of them hits the San Andreas fault. Massive earthquakes cause rampant destruction leading to (spoiler alert) the death of Lois Lane. Who is Superman without Lois Lane to connect him to humanity? It is a devastating loss that will be impossible to overcome.


In The Fellowship of the Ring, as the Fellowship navigate through the mines of Moria, Gandalf faces off with a Balrog (demon) but as he defeats this monster of fire and smoke, the monster gets one last attack, pulling Gandalf into the depths of Moria. Gandalf, the most powerful entity any of the Fellowship know, is lost. And now the ring asserts power over Boromir as Saruman’s super orcs attack the grieving Fellowship. Frodo can trust no one, lost his greatest ally, and is menaced at every angle.


Transforming Player Loss Into a 2nd Act Ending

What does this have to do with D&D? As I mentioned, D&D isn’t a novel or movie. If you force a story structure onto the game, then it stops being a game. The moments are predictable. The characters get something that is sometimes referred to as plot armor and the DM begins to remove agency from the players, making them passive consumers of a story instead of active participants in a game.

Can you sense the but? But, we can take the random moments and use them to craft a structure. Or at least give structure to specific moments of a campaign.

This is key to remember: I am not saying you bring the campaign to an early conclusion because of these events. What I am saying is taking a complete failure caused by the characters, and making it part of the structure of the campaign. Turn it into a Second Act – Everything Is Lost moment. Which means you have to do more than beat the characters in combat. You will need to truly make the character lose everything.

Pile It On

First thing is you need to pile it on. First, I would recommend that once the TPK seems inevitable, you pause the game. You need to give yourself time and room to maneuver which becomes harder if the entire party is killed. Bring it to a point where the players are clearly going to lose. Severely outnumbered and resources are dwindling. Maybe one or two characters are dead or making death saves. You don’t need to wait until there is one adventurer left standing to pull this move. All that is necessary is a general consensus by the players that their characters are hosed. You don’t want to take away a heroic moment away from the players if they think they can pull it off.

You now need to describe how thismment ripples outward. Loyal allies are corrupted or destroyed because of the character’s failures. Sanctuaries are destroyed. Remember in Serenity (spoiler alert) right after Shepherd Book gets killed? Zoe says they need to send a message to every person who has ever helped them. And then the screen cuts to images of fire and destruction as The Operative tells them that he could not let them hide or run.

Failing to save Shepherd Book was failure enough. Piling it on by destroying every possible safe haven the crew had, forced them to take dangerous actions to get clear of the relentless Operative which also led to a massive resolution between the Reavers and the Alliance.

When I say pile it on, I mean, don’t hold back. Family heirloom sword? Lost. The honor of the Paladin? Ruined. The faith of the Cleric? Shattered. The wizard’s spellbook? In the hands of the enemy. PILE. IT. ON. The characters may only be at level 3 when everything went sideways. Doesn’t matter. This also may not be the only time you do this to them during the run of the campaign, just don’t do this too often as it will become trite.

What you are doing is taking the game and the random events of the game and making it a structural part of the story. You are making it the end of the second act. This means you also need to plant the seeds of the third act.

Plan for the Restart

You have the characters on the metaphorical ropes (or literal ropes, I’m not here to judge your campaign). The entire party may be making death saves as the Warlock realizes Eldritch Blast won’t get him out of this sticky situation.

At this point if the adventure isn’t truly the climax of the campaign, you should be sweating bullets and questioning if you screwed up. Before you finish off the characters and gloat over their dead bodies, you need to be thinking about the resurgence.

I want to make it perfectly clear that I am not saying to turn the failure into a success. What I am saying from this point on is this is the point the failure allows from a triumph or a tragedy. The characters may be lost for good. That is the nature of D&D and I am afraid too many people playing lose sight of that aspect. I am not a killer DM by any stretch of the imagination, but I need to make sure the death of a character is a possibility at any given moment in the adventures I run.

I mentioned earlier I played for a long time where I protected the characters. Coddled them to the point where the game was just us hanging out. There were no stakes, the threats became comical to them.

Character death is a key aspect of the game which should never be diminished. D&D consists of a carrot and stick system. The characters do well, they gain experience and gold, which might translate into new abilities which keeps the game fresh. The stick is death. D&D has several ways to thwart character death with resurrections and such, but the idea that the character the player has invested time and energy into bringing to life might no longer exist is a BIG OL’ STICK. You need that stick to keep the game on track.

To start planting the seeds of rebuilding you need to pause the game. Seriously, before the final killing blow is struck, you need to cliffhanger the game. Everyone at the table is probably very well aware this is a TPK. That final blow can wait. This is also the moment when you can pause and visit other parts of the campaign world where you can detail how this failure by the character’s has caused damage across the world.

The destruction of allies and resources important to the characters. Siblings are forced into slavery. Lovers are kidnapped and locked away in towers. Mentors are killed without mercy. Nemesis … nemesi? Nemesix? Rivals rise in fortune and power. That shopkeeper that the players love even though he over charges and never has anything good? Yeah, she loses everything she has.

You might not fully know why all of this is connected to the character failure yet. You are filling time and laying it on as thick as you can. You want to end the session on this massive cliffhanger.

What happens next?

Now you plant the seeds. You have had a moment to think about the situation the characters are in. One of the suggestions that I wish I could remember where I read it — I thought it was in the DMG or Xanathar’s but I can’t find it — is to stop the action with the current characters, and hand the players some pre-generated characters with a specific mission. Then have those pre-generated characters stumble upon the moment of the TPK and allow a chance for the players to save their characters.

This is a fun and engaging way to give the players a chance at saving their characters. And it is just a chance. It isn’t a guarantee. Things could still go wrong with this second group of pre-generated characters.

Another option is to time jump. Advance the story ahead 6 months or a year, have the characters alive and well, but no longer adventurers. They’ve lost everything and are scattered across the land. Together they tell the story of how they survived and how they have suffered because of that event. If you choose this route, then you don’t have to pile it on, you can let the players do it themselves. You’ll be amazed at how quickly the players will disfigure themselves, remove abilities, and make their characters’ lives hell.

Another type of time jump is to jump forward in time with only those characters who made their death saves. Treat it like the end of Avengers: Infinity War. Characters have died, life has gone on. You will have to narrate what has happened between then and now. Characters captured, sold into slavery aboard a ship, rescued after a shipwreck, and now trying to rebuild what they once were. This option is a downer, requires a bigger jump in time which can really throw a wrench in a campaign.

Both of these time jumps are meant as a restart for the characters and the campaign. It allows the players to keep their characters, but penalizes them in terms of time and resources.

I do strongly recommend that you do not choose to imprison the characters. I know there are many great stories that can be told relating to prison breaks. The Dark Knight Rises puts Bruce Wayne in a prison that he must escape from and it is pretty awesome. The problem with playing prison adventures where the entire party is behind bars is the actions are so limited that it becomes frustrating and boring. It is like having to plan a heist adventure with no outside guidance. If you do choose this option, then at least allow one or two characters to escape in order to work the problem from a different angle. Or you can make sure the next adventure is the prison break and an fellow prisoner already has a plan but was looking for just the right people to enact it.

One of my favorite storytelling tricks is to do a prequel scene. Choose one of the still up and able characters and build a scene from their past for them and the other players to play through.

Playing Out an Example of the Prequel Strategy

For example, Nekas the human Rogue, Taneru the dwarven Ranger, Tarbul the half-orc Barbarian, and Camilga the half-elven Sorcerer find themselves at the mercy of Yudgab the hobgoblin chieftain. Tarbul is the last one standing facing four wounded but very much alive hobgoblin soldiers while the chieftain bellows, “bring me their puny skulls! I want to use them to drink their blood!” It is curtains for our intrepid group of adventurers…

Or is it?

Flashback to Tarbul’s youth where he is hunting with his clan. The barbarian’s player gets a new version of the character sheet, essentially a Level 0 barbarian or something more directly tied to his backstory, depending on how developed it was. The other players get other characters in the hunting party.

The mini-adventure plays out where there is a challenge eerily similar to the situation that has put the players in this position. In this scenario the mini-adventure leads the party to a point where they are surrounded by dire boars, and cut off from the master hunters.

The boars cut them off from each other and there is a moment where the young barbarian intimidates the boars into submission with a mighty warcry that comes from frustration, anger, and desperation. While the boars temporarily flee, the characters were able to regroup and escape. It was a lesson learned in the past which was forgotten… until now.

Returning to the present moment, with most of the party dead or dying, Turbal recalls that moment in his past. He can try it now. Use an Intimidation check with Advantage to stop the attacks for a moment (DC 12 – 1 turn, DC 14 – 2 turns, DC 16 – 3 turns or something… you get the idea, let the amount of success give them more breathing room to regroup and set the DC to be a small challenge to the PCs based on their level.) A success should have some specific results. Any character currently making death saves automatically stabilizes at 1 hit point. The party gets 1, 2, or 3 turns to take specific life saving actions including spells, potions, and running away!

The party isn’t out of the woods yet. Everything can still go wrong, but a potion or a heal spell can be used, a plan for retreat can be quickly assembled. The key here is there is no guarantee of success, and even if they are able to extricate themselves from this predicament, their entire safety net of allies, family, and resources has been disrupted.

Assuming the characters survive, you’ve brought them to their lowest point. It is time to offer them a path to redemption. To be able to reclaim lost honor, rescue captured loved ones, find lost heirlooms, and beat the hell out of the bad guys. So that is the key to this moment, even if you weren’t ready for it in the campaign, you need to put the characters on a path to recovery, a path to a climactic moment where they are not only have an opportunity to be redeemed but have a chance to close out a key plot point in the campaign.

This is not bringing the campaign to an end. It isn’t the final fight with the BBEG. It is tying up one plot point related to a character arc or with the big campaign story. If the adventure was early on in the character’s adventuring career and the adventure itself had little to do with the big campaign plot, then you may not find it worthwhile to go to this effort as it may seem weird why a swamp dweller and his trained swamp rats were able to cause such havoc in the character’s lives.

What does all this actually mean in terms of gameplay?

Boiling all this down away from the pretentious “3-Act Structure” which honestly cannot be applied to a game where the players have so much control over the flow of the story. And honestly, they don’t care about the structure of the story, they only care about what is happening to their character right now.

What I’m saying in very simple terms, is during regular gameplay while on an adventure linked to the bigger story of the campaign, if the players’ luck turns against them, it is possible to turn it into a story opportunity. Instead of killing off characters outright, doing a TPK, or even worse have a deus ex machina moment where the players are saved through literal divine intervention or through the arrival of a more powerful NPC, provide a way for the players to save their characters and turn the scene into a story moment.

The difference is something that is a real bummer in terms of gameplay becomes epic in terms of the story being told. It does create more work for the DM and can derail carefully plotted campaigns, but if you “flow with the arbitrariness” the end result is so rewarding for players and the DM.

Published by Sean D. Francis

Sean D. Francis is a technologist, writer, and geek. He podcasts, makes video, and dabbles in all the geeky genres including horror, sci-fi, and fantasy.

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