My Players Overcomplicate Everything

Marathon planning sessions turn quest that should have been a cakewalk into a musical comedy of errors


This post contains minor spoilers for side events in Baldur’s Gate: Descent into Avernus.  There’s nothing plot critical, but you’ve been warned.

I had been running a game of Baldur’s Gate, Descent into Avernus, for a few months when this story took place.  My players are all friends of mine I’ve been playing with for years.  I love them to death, but now and then they do something that runs me up the wall as a DM:  come up with the most convoluted plans for solving relatively simple problems.  This incident isn’t the first time it has happened, but it is notable for how spectacularly it went awry.

Our cast is this:  a human rogue who is an acolyte of Kelemvor, an aasimar artificer and member of the local nobility, and a yuan-ti fathomless warlock whose patron is Dagon, the chaotic evil Demon Lord of the Shadowsea. The party is rounded out by a couple of NPC sidekicks.  The warlock makes absolutely no secret about their patron and openly worships Dagon, which is a regular source of in-game tension with the rogue.

For those who haven’t read Baldur’s Gate, Descent into Avernus, there are a lot of characters and locations that are described in the book but not directly tied into the plot.One is a sahuagin priestess, Oshalla, who has been living at the Elfsong Tavern, and who was exiled after a failed coup.There is also information about the Temple of Umberlee, which has secretly been giving money to a group of sahuagin in exchange for leaving the city alone.  The temple also leaves messages for the sahuagin to attack certain ships that aren’t donating to Umberlee.

I decide it would be a fun little side-quest to have the warlock get a mission from their patron:recruit Oshalla as a follower of Dagon, or kill her if she refuses.  If she joins, Dagon will give her the power to succeed in her next coup.  My goal was two-fold; give the warlock a chance to use their underwater abilities before the party had to travel somewhere that made them useless, and make it clear that Dagon was not the benevolent father figure the warlock treated him like.

At the start of the session, the warlock has a dream in which they get their mission.  I reason that since the rogue has made no secret of his distaste for Dagon, the warlock might try scoping out the situation solo, or at least being judicious about who they tell about this mission.  I even planned the encounters for this around the assumption that the warlock might be acting alone.  So, what does the warlock do the second after their patron gives them this mission?  

Tell the whole party all of the details.  Including the part where if the warlock can’t recruit Oshalla, the warlock needs to kill her.

After talking it over, the warlock goes to meet Oshalla with one player and one sidekick as backup. As expected, the rogue refuses to participate.  Oshalla says she’ll do it, but only if the warlock can prove how helpful Dagon’s aid can be.  She tells the warlock that the Temple of Umberlee has been giving money to her former kingdom, and that this money was critical to keeping his guards on the king’s side.  If they can stop the next payment, it should destabilize things back home and give her an opening.

The warlock tells this to the party.  The artificer knows that once a month, Umberlee’s followers take the tithe money into the water by the temple and leave it there as an offering.  I thought the solution was obvious.  All they had to do to succeed was wait in the water after the money was left and leave before the sahuagin showed up to take it. Both the warlock and their familiar had a swim speed, so this should have been a milk run.

Boy, did I call that one wrong.

As the party discussed the problem, they somehow got it into their heads that the money going to the sahuagin was being skimmed from the donations.  In hindsight, I probably should have had one of the sidekicks speak up and correct them, but I didn’t want to railroad my players.  So instead, they decide to go to the Temple to see if they can get more information.  I try rolling with it, hoping that after they get stonewalled at the front door they’ll move on to something else.  Surely they wouldn’t do something as stupid as confess they know the Temple’s biggest secret, right?  If only.

Thirty seconds into the conversation with the high priestess, the warlock blurts out everything. The high priestess implies that their church is protecting the city from sahuagin attack, and warns the party against defaming their religion before slamming the door.  The party debates breaking into the Temple to look for clues before one of the sidekicks points out that they have now been alerted to their intentions.  At this point, I basically told the party that they had a few days before the “donation” was scheduled to occur, so they should get back to the main plot.  I unclench and brainstorm ways around this.

Skipping forward a couple sessions, the party had reached the end of a dungeon and returned to this mission.  During the dungeon, I gave the party a phial of love in their loot.  My hope is that they think to use it on Oshalla to convince her to accept Dagon as her patron without having to steal from the Temple. They had previously discussed poisoning her and then using the antidote as incentive for her to accept the deal, but balked at the price of ingested poisons.  But by the time they started planning again, they had forgotten the potion existed.

The party considered and discarded multiple plans, eventually settling on one where the warlock’s familiar would go invisible and watch the donation get deposited, then grab it when it was clear while the rest of the party was nearby inside a rope-trick hidey-hole.  But by the time the decision was made, we had to call it for the night.  We resolve to pick up here next time, which was a couple of weeks later owing to one player moving.  By the time we resumed, everyone had forgotten which plan they settled on.

After nearly an hour of trying to re-invent their plan, the rogue decided he would be on the shore to be a distraction for the acolytes of Umberlee, while the others were either waiting in the rope trick or hiding underwater.  I had assumed the rogue would start the distraction *after* the acolytes came out of the water, having left the donation on a small altar 15 feet underwater.  Or that after the donation was left, they would try to grab it.  I was wrong on both counts.

As three acolytes headed to the water with the donation, the rogue started his distraction, telling the story of how Garl Glittergold once humiliated Umberlee using nothing but a fishing net and a chicken pot pie.  I tried to roll with it had two acolytes continue while the other stayed behind to lecture the rogue.  I think “OK, this is a curveball, but all they have to do is wait for the acolyte with the donation to leave it at the bottom of the stairs”.  That’s when the warlock says “I have my familiar try to grab it from her”.

Initiative is rolled, and things quickly devolve into chaos.  The acolyte who was attacked by the familiar shouts to the others.  The rogue attacks the one acolyte on the dock but runs off without downing her, leading to her running inside to get the priestess.  The other acolytes had no prayer against four level 5 characters and quickly went down.  They party decided they needed to bolt, which is true because they’re a round away from the high priestess and some other acolytes jumping into the fight.As they ran, I flipped a coin and asked someone to call it to decide whether or not the priestess got a good look at them as they fled.  The player called it, so she did not.

While much of the gold was lost when the acolyte and familiar were wrestling with the basket, the players got what they came for, including evidence of the hits being ordered on ships.  Oshalla accepted Dagon, and the warlock’s mission was completed.  So while it all eventually worked out, the path to the goal was far more complicated than I anticipated.  

Looking back, I’m still not sure how much of the debacle was my fault as the DM.  I probably should have predicted some of their choices better, and I could have used the sidekicks to correct them when it became clear they misunderstood something an NPC said.  Oshalla also might have told the party how many sahuagin would likely be in the group sent to pick up the donation so that the party knew how seriously to take the threat.  But none of that changes the fact my players spent four or five hours over three sessions planning for a side mission that could have been completed without ever rolling initiative, and the plan they came up with went comically wrong.

TLDR:  Marathon planning sessions turn quest that should have been a cakewalk into a musical comedy of errors


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