Roleplaying games are as much an exercise of luck as they are of skill or drama and it’s in this element of luck that a beautiful little quirk can be found. An optional rule for Dungeons and Dragons is to consider this luck by involving a ‘critical’. A ‘critical’ is when a player rolls the maximum or minimum number on the dice. In the case of the D20 system, rolling a 20 is considered as a ‘critical success’ under these rules, usually resulting in an automatic success on an ability check and extra damage for a weapon attack. Opposite this is the critical fail, when rolling a natural 1 results in an automatic and spectacular failure of a skill or attack. As soul-crushing as a wrongly placed critical fail can be for players in a campaign, it can also be a brilliant spark of creativity in certain situations.
Welcome to From the DM’s Chair, I’m Shadowonthewall and today, we’re going to be talking about the nineteenth session of my D&D campaign: Dorvine and the lessons I learned whilst running it. This week, we’ll be discussing how critical fails can actually make a game better and some talk on crafting side-quests. My assassin avoiding adventurers are as follows:
Dion is Kassadin Lightfade, the Chaotic Good Tiefling Fighter.
Joey is Nikita Tomasovna Nikinova, the Chaotic Neutral Tabaxi Rogue.
Lukas is Teoku Skia, the Chaotic Neutral Shadar-kai Warlock.
Beth is Lady Elizabeth Grey, the Chaotic Good Human Barbarian.
Jacob is Doctor Eddard Von Keppler, the Chaotic Good Human Cleric.
Aimee is Erulissë Durfain, the Chaotic Neutral Drow Rogue.
All character art drawn by Dion Russell, whose other work you can check out here: https://www.deviantart.com/floodrushforever.
Last session, the Fellow Vagabonds arrived at the town of Hearthome, escorted by the Paladin Ulrico, seeking to gain more support for the fledgling thane Symon and also allowing Kassadin to prepare a new set of dragon plate armour. Settling a base at the local temple of Kelemvor, where Eddard’s childhood friends Louise and Hugo called home, the group took their time to explore the area. Whilst shopping at the market square, Elizabeth managed to gain part ownership of a small trading store with the help of travelling merchants Peres and Pip. Shortly after, the group were assaulted by a gang of gunslingers attempting to assassinate Lady Grey. After a bloody battle, the Vagabonds stood victorious. They took the survivor, Jareda, back to the temple and interogated him. Jareda bought his life with news on the Thieves Guild, Clear Skies, and the identity of their leader, a noble by the name of Atticus Trizane. With Atticus plotting the death of Elizabeth’s father under the moniker of ‘The Albatross’, the party were determined to shut him down and help their new found ally, Jareda, to get a new life.
The party awake the following day to the sound of a bell tolling. Eddard immediately concludes its an alarm from town and the party gather together to investigate. The central courtyard is swarming with villagers and a large presence of soldiers. A stage has been raised in the centre of town and atop it is a tall Goliath man with long dreadlocks curled back into a ponytail. War-paint marks him as a fierce fighter and his rippling muscles peeking from leather armour as a barbarian. This is when the party first encounter General Huxx, the local military leader. Huxx calls to the crowd about the continuing disappearances. They have become too much for him to ignore. Considering two merchants were abducted the night before, suggesting an acceleration in a kidnapper’s agenda, Huxx announces he is instigating a lock-down of the town and a curfew until the issue is solved.
As the soldiers spread out to begin their blockade of the important roads, the party try to speak to Huxx. Kassadin and Eddard break from the party and attempt to reason with him, but their attempts are fruitless. Huxx is a stern proud man, refusing any of their comings and goings until the force responsible for the disappearances is brought to justice. Eddard volunteers his services and Kassadin, sensing both some fresh gold and a chance to gather support for Symon, agrees as well. Huxx, pleased to have some allies, shares all the information he has managed to gather with the pair.
The disappearances have been a common occurrence for the last few months, starting just before the new year. At first, men and women began disappearing, alternating every other week. Then, only females began disappearing, young human women. The last woman taken was named Martha. All the investigation into her disappearance proved fruitless, despite Martha’s mother blaming the local dryads of the swamp, whilst the rest of the town accused the local rat-catcher, Rudolff Cussack. Huxx notes that the last victims break this rule yet again: both being males, a genasi and a halfling respectfully. Kassadin quickly deduces who the pair of merchants are: one being the mechant he sold the dragon blood to the previous day, the other being the halfling Pip, one of Elizabeth’s new partners in business.
Despite the disappearance of Pip, Elizabeth is the hardest to convince. Family is everything to her and she’s still deeply upset by the ambush the previous day, desperately wanting to rescue her father from the mysterious ‘Atticus’ and pursue her own efforts, rather than play around in the mud. Eventually, the party manage talk her around but Elizabeth is still eager to leave town as soon as possible, planning to head to Wreath in the North-East to save her father and then Blackbridge to the North-West to destroy Clear Skies once and for all. With the dear lady pacified, at least agreeing to deal with whatever madness is going on, the group try to draw up a plan.
It’s only then that they realise one of their number is missing.
No-one notices as Nikita sneaks out of the temple early in the morning. Even fewer noticed her swimming through the shallows of the swamp and racing cross-country over the wild bushes. Her target is Orlon, the current capital of the young thane Symon’s holdings and the place where he and his guard, Mayhem, are currently based. Nikita bounds across the swamp, taking the most direct route to her ‘wonky’, and barely avoiding the dangerous bog as she runs. Bypassing any attempt at a blockade, Nikita eventually arrives at Orlon, exhausted and filthy. Mayhem and the Cinder Guard welcome her back to the Lonely Dragon tavern with open arms and set her by the fire. Symon, in particular, is glad to have her back, enjoying their playful banter. Nikita contemplates the prospect of a bath when there’s a sudden knock at the tavern’s front door.
It’s the reason she’s come all this way.
Nikita’s rival, Alexei, has followed her.
A proud tabaxi with the pattern of a snow leopard, Alexei easily commands the attention of everyone in the room by his mere presence. He greets Symon warmly, before attempting to gain funding for his archaeological research. Nikita does little to hide her fury.
“The thane does not hold audience with two-bit treasure hunters!”
“Oh,” Alexei muses, “then why does he enjoy your company?”
Nikita fumes, unable to think of a reply. Just like Alexei.
Always one step ahead, always stealing her thunder.
Symon comes to her defence, rebuking Alexei’s claims. Sadly, the boy is new to his title and ends up straight in Alexei’s masterful trap. With Symon’s known approval of adventurers, Alexei issues a challenge for Nikita before the eyes of the thane to collect a rare assortment of valuable relics in the span of a month. The greatest discovery wins.
Nikita accepts the challenge to spite Alexei. Pleased with his move, Alexei soon retreats with his follower, Warren. Nikita is well-aware she’s taking Alexei’s bait, but she has still stopped Symon from speaking with him, a good thing too.
Alexei’s silver tongue would easily demolish Symon’s fledgling will. Previously having left Symon a message of meeting at a set of old ruins nearby, Nikita was afraid her rival would take a chance to recruit the thane to his side. Lucky for her, Mayhem had refused Symon leave of the tavern, at least until his armour was ready and the guards fully stocked up.
If not for that, Nikita considers, Symon might have gone blundering straight into Alexei’s paws.
Yet another thing he has tried to take from her.
Nikita finally relaxes in a bath and her and Symon get the chance to talk, Nikita telling Symon stories of her travels. When Symon learns of Nikita visiting Hearthome, he jumps on the subject.
“Nikita…could you take me there?”
His mother had forbidden him from going. Of course, this had only made Symon more curious and recent events are pushing him towards a new goal.
“If I am to rule, I cannot rule in fear. I need to know whatever it was my mother was trying to hide from me.”
Nikita agrees, but explains to Symon she’d feel safer if the pair have an escort. Symon has just the person in mind and recommends an old ally.
With Nikita having disappeared from Hearthome, the rest of the Vagabonds try to entertain themselves for the rest of the day. Elizabeth and Erulisse go to the forge to purchase some weapons. Despite the busy atmosphere, the Dwarves having arrived from rival forges to help construct Kassadin’s armour, Elizabeth manages to get some knives for Erulisse and inquires about enchantments. Joriah Khan, the smith, informs the pair that she doesn’t do any enchantments herself but recommends Cailen, a celebrity of the area who has been frequently mentioned as the group have explored the town.
With Erulisse all kitted up and Elizabeth ready to rest, Keppler makes the first move in his latest scheme: summoning Kassadin and Ouskarr to the crypt where Jareda is being held. Yuvari has been watching over him in the meantime and the two seem to be getting along, though he has been subject to her terrible attempts at entertaining him with terrible card tricks.
With Jareda firmly willing to cooperate with the group and helping them deal with Clear Skies in exchange for his safety, Eddard leads Kassadin and Ouskarr into a room of the crypt and explains his plan.
Or, rather, doesn’t.
“What would be a terrible idea,” Keppler explains, “is if you would take a body, cut off the hand und disguise it in the clothes of our friend, Jareda. Then, if you were to, say, smuggle it out and put it on display so that Clear Skies would think Jareda was dead, that would free him up to function as our agent. However, it would also be incredibly disrespectful and impossible to do. Even if you took the sewer exit in the dark of night, unlocked the gate with the key found in the pantry and follow the system for three stops, note it Kassadin, three, to get out into the city. Nope. Impossible and I would not approve such a thing. Now, if you excuse me, I will leave you boys to not do illegal activities in here but will go walk around with Louise for, say, a few hours at dusk that would be the perfect time to move a body. Hypothetically.”
Keppler departs, leaving Kassadin and Ouskarr to watch after him, clear confusion on their features.
“If he wouldn’t want us doing that, why tell us how to?” Ouskarr asks.
“Come on, looks like we’ve got a long night ahead of us.”
The day passes quickly and, in the shadow of the night, Kassadin and Ouskarr finally get to work with Keppler’s ‘plan’.
“We should wear masks,” Ouskarr grunts.
“What?” Kassadin grunts, “no, no masks. We don’t want to look suspicious.”
“We’re sneaking around with a body in the sewers,” Ouskarr points out.
“Exactly!” Kassadin rallies, “we’re gonna be under arrest if we masks or not!”
“Could we at least have codenames?”
Kassadin sighs, flashing a grin.
“Cool,” Ouskarr cheers, “I’ll be Big Green…and you can be…”
“I was going to see ‘Horn-Lad’ but your name was better…”
“Taking a body from the crypt and preparing it to look like Jareda, severed hand and all, the pair attempt to sneak through the sewers and find a place to dispose of the body. The idea, as far as Kassadin guesses, is to dump it somewhere noticable without being spotted.
Only Ouskarr is clumsy and drops the body in the stream of sewage.
Shortly after retrieving the corpse, the pair try to climb up onto the surface.
Only for Ouskarr to attract the guards with his clattering.
The pair escape into the sewers, running full pelt.
Only for a guard to follow them down and call after then.
“Big Green, he spotted us!”
“What do we do Kassadin…I mean, Big Red?”
“Knock him out!?”
Without needing to be told twice, Ouskarr reels on the guard, rendering him unconcious with a swift chop to the neck.
“Good,” Kassadin replies, “make it look like he tripped.”
Ouskarr slams his entire weight on the man’s leg, breaking it one solid notion. Kassadin screams.
“I didn’t mean break his leg!”
“I’m not good at improvising!” Ouskarr howls back.
The two break into a run, sprinting down the sewer tunnels before finding a new manhole cover. Entering out onto an abandoned street near a farm, the two take their chance to sneak into the field, looking for a place to put up the body.
“Where can we dump him?” Kassadin grunts.
Ouskarr, always the man with the plan despite his panic, gestures to a nearby scarecrow. Kassadin loves the idea and the two string up the dead corpse, just in time for a pair of passing guards to spot something going on in the fields. With no way of easy escape, Kassadin decides to bluff it, pulling Ouskarr over and pretending to be just another drunkard peeing on the field.
Despite their proximity towards a sudden dead body appearing, the guards are taken in by their crafty deception and quickly escort the pair back to the temple. Eddard, having just returned from his walk with Lousie to speak with Huxx, reprimands the two for their drinking harshly, Yuvari aiding the deception by once again donning her ‘Nyessa’ disguise spell. Despite being forced to pay a fine for the pair’s disorderly conduct, their plan seems to have gone without a hitch. Now, it’s time to get the next matter at hand: investigating the disappearances in town that have led to the blockade.
The Vagabonds, sans the anti-social Erulisse and the weary Teoku, make their way towards the centre of town for their next investigation. Using Keppler’s knowledge of the town, the group manage to easily locate the house of Rudolff Cussack and engage in your standard display of heroism: breaking into the man’s house and interrogating him. Rudolff, a thin rat-faced man, immediately breaks under the presence of ‘Kelemvor’s Inquisition’. He wisely confesses that he was the last person to see Martha alive. The two were in love and planning to elope when a strange metal suit of armour emerged from the sea and kidnapped her. Eddard dismisses the idea as foolish, but Rudolff promises to lead the party to the space where it happened. Before they leave, Kassadin robs the man of his last bit of silver.
Back in Orlon, Nikita recruits an old ally of the party, the displaced Paladin of Bahamut Faeriel, in her efforts to sneak Symon to Hearthome. Faeriel agrees, but is clearly reluctant, believing Symon might come to harm. Nikita is confident such will not occur.
If only she knew
Trekking back across the swamp at a more reasonable pace, the trio reach Hearthome in the dead of the night. Their arguing in the swamp, however, attracts unwanted attention. A large metal hand reaches from the water, attempting to pull Symon and Faeriel into the bog. Nikita jumps out at the mysterious figure and discovers an immense frame beneath the water. With a whirr of energy, the creature races through the water, following it along to the shore. The Vagabonds, investigating the area up ahead, look just in time to see the strange figure burst onto the shore. A large suit of armour, glad in a golden metal, looms above. Simple and sleek in design, the armour is a clear clockwork creation, clicking and ticking with each movement. The armour throws Faeriel forwards and into Kassadin before scooping up Symon, sealing the young thane away in its hollow frame. The Vagabonds ready for battle as more of these strange creatures begin emerging from the swamp, metal armour gleaming in the moonlight and fierce ticking whirring away inside. Each suit looks up, studying their prey.
Not to the males of the party, but the females.
“Readying capture protocol…”
The Vagabonds have found their kidnappers. Soon, they will wish they hadn’t.
And thus concludes the nineteenth session of the Dorvine campaign. Overall, I feel I’m happy with the new recap portion: a more condensed article highlighting important moments seems to be working. Plus, it means I can also work harder and put more focus on the main reason I wanted to do this: discuss advice I have for new DMs and talk my process.
Critical Failures aren’t always bad, they can make for an interesting development of the story.
As much as I had been looking forward to revealing the evil machinations that lurked in the swamp, walking away from this session, I found the best moment to be one I hadn’t even thought of: Kassadin and Ouskarr sneaking through the sewers trying to fulfil Keppler’s plan. What started out as a simple mission turned into sheer amazingness with twists, turns and dramatic events. All because I and Dion kept rolling critical fails.
Critical failure is a great way to invoke drama in simple situations. A twist of fate can be exactly what you need to create new and more interesting situations. Usually, when critical failures occur, it can be a devastating occasion for a party: a missed save resulting in a brush with death or even a tragic diplomacy check making an enemy of a friend. However, if this session showed anything, it is that even in failure, you can create amazing moments and brilliant experiences for your players.
The recurring failures meant that Dion had to think outside the box and approach new strategies from his usual comfort zone in an event that really resonated with the rest of the ground and was thoroughly enjoyable, both to watch and to play through.
Be careful when constructing your quests, your players will miss details.
The side-quest for Hearthome was one I constructed in great detail with lots of possible ends to investigate. I wanted to create a compelling mystery and really give the players a chance to investigate a variety of developments in order to fully expand Hearthome as a setting.
This is not exactly how things happened.
The party checked one avenue, the ratcatcher, and luckily, it gave them the result they needed, with the man leading them to face the Clockwork creatures kidnapping the people of Hearthome. Due to some previous talks throughout the session about the town’s resident ‘tinkerer’, Jacob managed to guess that it was none other than the eponymous Cailen of Cailen’s Tower was indeed the mastermind behind the disappearances.
This would have a really good reveal, if the players had actually interacted with Cailen at all before he was revealed.
The truth is that mysteries framed as situations like this can be hard to run in a session, due to player interactivity. We can never truly expect our players to follow our intentions perfectly, and thus, as DMs, we need to remain flexible, always having alternate paths or solutions planned just in case the players wander too far off course. The main pieces of advice I can give regarding forming quests like this is to design the mystery less as a plot and more as a framework and to make each of the key elements of the mystery as clear to the players as possible.
Plots in D&D, whilst possible, can sometimes come off as a form of railroading so it’s usually best to keep your plans open-ended as a ‘situation’, allowing for the players to have a greater chance of interaction but also allowing us as DMs to react easier to our players.
Showcasing key elements, meanwhile, is important because it helps give the players a deeper understanding of the mystery and makes it less likely they’ll miss anything. Sure, an approach like this can lead to overwhelming your players or flat out ruin the mystery, as what happened with me, but it also means that the information the players need is all out in the open for them to explore. Whenever the players went about the town, I tried to namedrop as many of the individuals involved as possible to give them a layout of the important NPCs in town and though no-one engaged with Cailen, most of the group had at least heard of him due to my heavy foreshadowing.
Splitting the party doesn’t ALWAYS have to end in death.
If there’s a recurring thing Joey is getting known for in my campaigns, it’s doing things separate from the rest of the party. Playing lone agent style characters like this can prove a little dangerous, as Megs found out the hard way, but as much as D&D is a cooperative game, players should be allowed to follow their character’s actions, no matter how desperate or foolish, so long as it doesn’t disrupt the rest of the play.
For Nikita’s trek to Orlon, even though I rolled for a random encounter, nothing happened and in hindsight, that was probably for the best. Nikita’s trek to Orlon was something Joey wanted to do in-character based on a note Nikita passed to Symon before leaving. A note which I, being the capable DM that I am, completely forgot about until Joey brought it up to me. Luckily, because of that, Symon was home and Nikita was able to bring him along just in time to be snapped her.
Though the plot-line was sudden, it ended quite well and reunited the party once more, which is a good lesson to take from it: splitting the party isn’t always bad. It’s difficult, sure, and, if you’re worried about it, you as a DM do have a right to warn your players before hand that you’d rather not do their events separately as you can’t balance things well (I left a player waiting for two hours and he forgot what he was doing, not my finest moment). However, if players do split up, it isn’t the end of the world and can be a chance for some interesting and in-depth role-playing. Combat can prove more difficult but combat isn’t always a definite in any situation. Either way, it’s good for players to explore their own agency and splitting up the party is just another way in which players can do that.
That’s going to be it from this segment of From the DM’s Chair. I hope you’ll join us next time where the Fellow Vagabonds unravel the conspiracy of Hearthome and we’ll be talking in greater depth about villains, their plans and motivations. Until then, thank you everyone for reading and I hope you’ve enjoyed today’s segment of From the DM’s Chair. Please leave a comment. Constructive criticism is welcome.