What's the consensus on whether or not an encounter stacked against a player can still be fair, if that player reaped what they sowed? Basically a completely one-sided fight that can result in player death unless the rest of the party takes strong action after the initial round.
Essentially the party leader has made multiple back to back negative choices.
She played it safe with their lives over a civilians while trying to raid a goblin hideout. Instead of executing a rescue on the civilian, they licked their wounds. Meanwhile the civilian was killed and replaced with a doppelganger. They knew the civilian was going through a prisoner exchange with a Drow, and the party didn't realize that the prisoner exchange didn't occur and that the Drow (Doppelganger) was missing!
She betrayed a parlay which would have likely outed the doppelganger as an impostor. She agreed to a parlay then after the enemy dropped their weapon, she executed him!
She failed to either roleplay effectively or roll insight during the subsequent social encounters with the doppelganger into realizing the doppelganger was an impostor.
The fatal encounter then occurs that is a waterfall of all her mistakes. She wakes up to the sight of the bedroom on fire, and an immense pain of being crushed. She sees a Bugbear standing over her getting ready for another swing. This multiattack has the potential to one shot her. A doppelganger who makes this attack would do a potential 8d6 + 4 damage on an unconscious creature, and another 4d6 + 4 on its second attack. The doppelganger then flees out the second story window. At this point the second player in the room could either try to stop the quickly building fire, to render aid to the party leader, to chase the doppelganger, or to get the remaining party members! It is up to him what happens!
While that is a wonderful cinematic event, it doesn't feel quite right within the bounds of the game.
Why didn't the player wake up to the fire, the smoke, and the noise of people freaking out that a building is on fire? Fires are one of the most dangerous natural disasters and without a modern fire department, it's not uncommon to see large areas of a city consumed by fire.
Why didn't the player wake up the moment the bugbear pinned them down? This is an iffy one, I can see an argument for both sides, but it still begs the question: shouldn't they get an opposed grapple, even if at disadvantage due to surprise?
Why didn't the second player wake up due to the same commotion?
At what point in time are you going to roll for initiative since this is a combat scenario? That could shift the dynamic of the encounter.
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I agree that the player(s) should suffer the consequences of their in/actions, that's an integral part of the game. I'd just be wary that you aren't forcing this situation on the player and not giving them the agency the would normally have in any other case. Consider some of these things, and what the other posts may have, and have fun, it sounds like this player might just deserve this kind of wake up call (pun intended).
I wasn't picturing the building on fire before the scenario. I was thinking that the players would be forced to choose between splitting the party between helping their downed ally, chasing the doppelganger, and putting out the fire.
A theoretical scenario would typically play out something like this: the party is at the Inn late at night and the Doppelganger is playing the part of the dwarf Gundren, engaging them in the plot and coating the truth in lies. The party has already commandeered a map from the doppelganger which he wants to destroy. They would have an opportunity to roll Insight vs the Doppelganger's Deception. Any player character who says they are naturally distrusting may have advantage on the roll. This will allow the party to roleplay their defensiveness at night and will increase the difficulty of the Doppelganger's plan being successful.
That night, the doppelganger goes to scout the player's bedroom. The player would have a roleplaying encounter and an opportunity to roll Insight as well. The doppelganger will try to exit the room leaving the door unlocked, and the player can roll perception on noticing him do this, if they state that they are suspicious.
If the player says that they take a long rest, then each player in the room may roll perception with a relatively high DC, say 18, to awaken from the doppelganger's actions throughout the room. If they succeed, they will see a small fire by the door (the map and other related items are aflame), the door is simply locked from the inside, and the window is open. They have another chance to see the doppelganger in the room as a standard stealth check, disguised as the Innkeeper if he needed to get keys to unlock the door, otherwise disguised as the bugbear chief from the previous encounter. If they see the doppelganger as the Innkeeper, he will attempt to warn them that the Inn is on fire, then will strike with a surprise attack. If they fail to awaken, then one of the players will awaken to the first attack from an oddly dressed bugbear. The subsequent attacks will likely have advantage since the player will be unconscious and then prone. The doppelganger then flees out the window, and the party can either give chase, help their possibly downed ally, or stop the fire.
At this point, the players may take a single interaction to make sure that the door is unlocked for their party members to join, otherwise they have to succeed on a Strength 15 DC to break it down. A single player can also take their action to stop the spread of the fire. For each round that they don't stop the spread, it spreads. For each round, they do, it shrinks. Starting with the first round, a single player only has to declare that they are doing that as their action to completely stop the fire, otherwise it quickly spirals out of control and after the first minute the entire room is on fire.
The doppelganger may then return to the Inn as the dwarf and continue his rampage!
It sounds like an interesting scenario, you're giving them plenty of opportunities to catch wind of what is happening. My only thought would be to use a Con save for waking up, can't really perceive while you're sleeping :) Stealth/Sleight of Hand from the Doppleganger would be around 15 DC vs the players' Con to sleep through the disturbance, if you feel like giving advantage to the Doppleganger, then the DC could be that 18 you mentioned earlier.
The overall plan sounds ok. However, I would never let the doppleganger have a crit against the sleeping opponent since, from a player perspective, it is just too much of the DM just saying it happened and perhaps wanting to kill the character in question. The DM could protest that there were all of these dice rolls made that the characters failed but it is still, from the player perspective, just the DM whacking away on a character with an NPC no matter how good the "cinematic story" might be in the DMs head.
In addition, even in the way you have described it, it actually sounds like punishment to the player for the character actions taken in preceding encounters. It shouldn't be punishment for what you, the DM, might consider poor or rash decisions that should have consequences, it should be just the actions in the world playing out against the players responses.
For example, why is the doppleganger still with the party at all? Once they escaped why didn't they just leave? Why would the doppleganger have a map and why would he allow the players to commandeer it if it was worth anything at all?
If it matters to the doppleganger maybe they should just steal the map and put it in the fireplace at the inn.
Why would the doppleganger appear as a bugbear chief from a recent encounter? Didn't the party kill them off?
I'd also note that the 4d6 damage depends on the doppleganger actually having Surprised the opponent. Surprise is very restrictive in 5e. In order to be "Surprised" you need to be completely unaware of the opponent, not just unaware of their intentions. For example, if an acquaintance you were talking to suddenly decided to attack you might be surprised but not Surprised in terms of combat. PHB p 189. It is of course up to the DM and if the character is actually asleep when the attack happens then they would be Surprised but there would be a lot of checks getting to that point.
For example, kindling a fire in the room is VERY likely to wake everyone up. Even having someone enter the room might be enough to wake someone up unless they make a very good stealth roll. You also mentioned that there are two people in the room, the odds of entering, finding a map, lighting a fire, moving to the bed of one of the characters and then executing an attack without any of the rooms occupants noticing should be pretty small.
Also, depending on the circumstances, it could be very hard to notice a doppleganger. They will typically be getting advantage on all the opposed deception and insight checks due to reading minds AND they are proficient at both skills and even in they slip, they are likely to be able to recover. If the players have accepted the doppleganger as whoever they are imitating then they may not be making checks. On the other hand, the doppleganger does not have any memory, personality or mannerisms of the person they are imitating. Anyone who knows the person well is much more likely to notice or suspect something is wrong though if they don't know that a doppleganger might be involved then they might just think they are sick.
Anyway, in my opinion, No :) .. the scenario you outlined wouldn't be fair to the player involved.
The campaign is Lost Mine of Phandelver. The party was aware that Gundren Rockseeker was being held prisoner in a prisoner exchange. In the original campaign, the Drow simply wanted Gundren dead and to destroy the map, and the party would have had the opportunity to protect Gundren if they simply tried rescuing him. However, since they blockaded themselves in and took the short rest, I figured logically their lack of bravery would result in a negative outcome in the NPC death. Rather than having Gundren simply be found dead, I felt like it was more dramatic if the doppelganger took his place. The party had a chance to find Gundren's dead body but they missed it.
I made a bit of a logical mistake last session in which the doppelganger as Gundren revealed the existence of the map among his things, and tried to destroy it in front of them, insisting that he memorized the location and the enemy must not get it. Logically, you are right, if he didn't want them to have the map, he would have simply destroyed it when he hid the body.
However, since I already made this mistake I thought IF the party brought up the map, the doppelganger would discuss it with them in a misleading way while ingratiating themselves in the party, while attempting to steal and destroy it. If he can not clearly get at it, he will try to steal it at night, setting fire to the personal belongings and escape in the cover of the fire. He is a doppelganger and they are supposed to only strike when cornered, however an easy target could certainly be a legitimate goal. Maybe only if his plan is interrupted, he will surprise them from hide, running standard combat rules. To me, it is important though that he would do this only while the player is doing their long rest, split up from each other, and out of their armor.
I think I'd like to point out that by not finding a dead body, all the players think that they successfully rescued the prisoner and that there were no consequences to their short rest.They don't see anything dramatic ... only the DM does.
In addition, a short rest is only a delay of an hour. If the travel time to wherever they were going to rescue this prisoner was on the order of hours there is no real way for the players to know that taking a short rest would make a difference. Were the players clearly informed that every second counted and that a delay in getting to wherever the prisoner was being held of even a few minutes could result in the prisoner being killed? (I'm not sure if there is any way in game for that information to be available to them but if there is such a time constraint then it needs to be clearly and logically passed along to the players ... otherwise they go on the rescue mission with the fairly reasonable expectation that an hour is unlikely to make a difference in the outcome of the mission.)
Also, whatever you choose to do in your game is fine. However, after reading it over a bit ...
The doppleganger and the bugbear king Grol are negotiating. Grol wants to sell the map instead of surrendering it. This negotiation could take as long as you like. In addition, the doppleganger wants to question Gundren to find out if anyone else knows the location of the mine. However, Gundren is unconscious at 0 hit points in the corner of the room. It will take some time for him to wake up naturally so he can be questioned. Likely easily longer than an hour.
Also, keep in mind that the doppleganger doesn't know that Grol has hidden the map in the treasure cache under the mattress though he might be able to find it if given time to search after the bugbear is dead.
So ... I am guessing the characters invaded the castle and decided that they were too wounded (or had spent too many resources) to continue at some point and decided they needed a short rest?
If that is the case then I think you needed to make them realize that their actions had alerted all the creatures in the castle. If they take the short rest then either all the the remaining creatures will likely be positioned to kill them when the short rest ends or will have escaped and that their mission will be a failure either way.
For some reason the characters didn't realize that there might be consequences to the short rest. Instead, it sounds like they short rested then went on and killed Grol and rescued Gundren and his possessions. Mission accomplished! so the short rest didn't matter (as far as they are aware anyway). They then leave and Gundren realizes that he hasn't destroyed the map yet, pulls it out in front of the party and proceeds to try to destroy it. However, from the sounds of it the party intervenes and steals Gundren's map. Why did Gundren allow that? Did Gundren point out that it is HIS map and they characters have NO right to take it!? What reason did the characters give for not giving the map back to its rightful owner and instead putting it with their own stuff as if it was their map? Are the characters evil or chaotic neutral? Do they think stealing things from people is completely acceptable?
If the map is important then Gundren should get it back, throw it in the fireplace and leave before the characters figure out he isn't Gundren. However, if the map is important to continuing the ongoing plot then perhaps Gundren did a poor job of throwing it in the fire since he is in such a hurry. He threw it in a ball and instead of lodging in the flames it falls down the back of the burning wood where it singes but doesn't ignite. If the players learn its importance they can try retrieving it from the fire.
Finally, I just wanted to comment on the reasons behind this plot development ...
"I figured logically their lack of bravery would result in a negative outcome in the NPC death"
"if that player reaped what they sowed?"
"Essentially the party leader has made multiple back to back negative choices."
"She played it safe with their lives over a civilians while trying to raid a goblin hideout. Instead of executing a rescue on the civilian, they licked their wounds."
"She failed to either roleplay effectively or roll insight during the subsequent social encounters with the doppelganger into realizing the doppelganger was an impostor."
"The fatal encounter then occurs that is a waterfall of all her mistakes."
All of these comments make the planned game actions sound like a personal vendetta or punishment for the characters taking actions you didn't like or considered inappropriate or unlucky even if these actions may have been completely in-character for the specific character involved. DMIng shouldn't work that way. You control the world and how it responds to the player actions or lack of them, without getting personally invested. DMs enable the fun and adventure, but they don't police the characters choices of what they decide to do. Anyway, there are lots of ways you can run with this ... you might just want to consider your motivation and make sure that the NPCs are interacting as their character would tend to have them do and not in ways you want just to make life more difficult for the PCs.
So basically, the party scouted with a Pact of the Chain Imp and discovered that Gundren was alive, and there was a negotiation over his release from King Grol to the Drow. They then decided to siege the castle from the front and successfully pushed the enemy forces deeper into the castle. They had a pretty good layout of the castle before even entering as the Imp passed its stealth checks to investigate so they knew what they were up against. The session ended and I refamiliarized them with the situation. That they should be aware that the Drow was going to take possession of Gundren immediately before the siege. I also made the character with the soldier background aware that while she has sieged a castle before, she is aware that they would likely fall back to deeper reinforcements and regroup for a pincer attack, and the best decision from her training would be to attack quickly while they were apprised of every enemy's position and the hostage situation. I also had Sildar warn them earlier that Gundren may already be dead, but he hoped that he was still alive. The party took their short rest yet blockaded their position, and while the goblins split their forces to prevent retreat, they failed to trap the party. I feel like I did not make the enemy forces overwhelming enough to properly reflect the consequences of the short rest.
"Why did Gundren allow that? Did Gundren point out that it is HIS map and they characters have NO right to take it!? What reason did the characters give for not giving the map back to its rightful owner and instead putting it with their own stuff as if it was their map? Are the characters evil or chaotic neutral? Do they think stealing things from people is completely acceptable?" This is a very good point. I felt like they thought Gundren was being rash. But yes, they essentially stole the map from him. I played Gundren as insistent on leaving out the secret entrance while the remaining enemy forces were regrouping. As soon as they tried grabbing the map from him, he relented as long as they agreed to leave immediately. So Gundren technically got part of what he wanted. I will definitely make this part of the roleplaying scenario next session.
"All of these comments make the planned game actions sound like a personal vendetta or punishment for the characters taking actions you didn't like or considered inappropriate or unlucky even if these actions may have been completely in-character for the specific character involved." So these choices were actually somewhat in character for her personality flaw, which is that she has survivor's guilt for a blood bath she was in, and no longer takes risks in battle. She is therefore, ruthless and would certainly execute a hobgoblin in a parlay, and would take a short rest to heal herself rather than risk hers or any other party member's life. She is also the one who explicitly stole the map from Gundren... she is technically Chaotic Good but I think she definitely shows shortsightedness and even evil tendencies in her character's personality.
I didn't want to 'punish' the player per se. If I did, I wouldn't have asked for advice on here, I'd have just done it! I did want to do something very dramatic so her character can realize that there are terrible consequences to her character's shortsightedness and flawed personality.
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What's the consensus on whether or not an encounter stacked against a player can still be fair, if that player reaped what they sowed? Basically a completely one-sided fight that can result in player death unless the rest of the party takes strong action after the initial round.
Essentially the party leader has made multiple back to back negative choices.
She played it safe with their lives over a civilians while trying to raid a goblin hideout. Instead of executing a rescue on the civilian, they licked their wounds. Meanwhile the civilian was killed and replaced with a doppelganger. They knew the civilian was going through a prisoner exchange with a Drow, and the party didn't realize that the prisoner exchange didn't occur and that the Drow (Doppelganger) was missing!
She betrayed a parlay which would have likely outed the doppelganger as an impostor. She agreed to a parlay then after the enemy dropped their weapon, she executed him!
She failed to either roleplay effectively or roll insight during the subsequent social encounters with the doppelganger into realizing the doppelganger was an impostor.
The fatal encounter then occurs that is a waterfall of all her mistakes. She wakes up to the sight of the bedroom on fire, and an immense pain of being crushed. She sees a Bugbear standing over her getting ready for another swing. This multiattack has the potential to one shot her. A doppelganger who makes this attack would do a potential 8d6 + 4 damage on an unconscious creature, and another 4d6 + 4 on its second attack. The doppelganger then flees out the second story window. At this point the second player in the room could either try to stop the quickly building fire, to render aid to the party leader, to chase the doppelganger, or to get the remaining party members! It is up to him what happens!
While that is a wonderful cinematic event, it doesn't feel quite right within the bounds of the game.
Why didn't the player wake up to the fire, the smoke, and the noise of people freaking out that a building is on fire? Fires are one of the most dangerous natural disasters and without a modern fire department, it's not uncommon to see large areas of a city consumed by fire.
Why didn't the player wake up the moment the bugbear pinned them down? This is an iffy one, I can see an argument for both sides, but it still begs the question: shouldn't they get an opposed grapple, even if at disadvantage due to surprise?
Why didn't the second player wake up due to the same commotion?
At what point in time are you going to roll for initiative since this is a combat scenario? That could shift the dynamic of the encounter.
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I agree that the player(s) should suffer the consequences of their in/actions, that's an integral part of the game. I'd just be wary that you aren't forcing this situation on the player and not giving them the agency the would normally have in any other case. Consider some of these things, and what the other posts may have, and have fun, it sounds like this player might just deserve this kind of wake up call (pun intended).
I wasn't picturing the building on fire before the scenario. I was thinking that the players would be forced to choose between splitting the party between helping their downed ally, chasing the doppelganger, and putting out the fire.
A theoretical scenario would typically play out something like this: the party is at the Inn late at night and the Doppelganger is playing the part of the dwarf Gundren, engaging them in the plot and coating the truth in lies. The party has already commandeered a map from the doppelganger which he wants to destroy. They would have an opportunity to roll Insight vs the Doppelganger's Deception. Any player character who says they are naturally distrusting may have advantage on the roll. This will allow the party to roleplay their defensiveness at night and will increase the difficulty of the Doppelganger's plan being successful.
That night, the doppelganger goes to scout the player's bedroom. The player would have a roleplaying encounter and an opportunity to roll Insight as well. The doppelganger will try to exit the room leaving the door unlocked, and the player can roll perception on noticing him do this, if they state that they are suspicious.
If the player says that they take a long rest, then each player in the room may roll perception with a relatively high DC, say 18, to awaken from the doppelganger's actions throughout the room. If they succeed, they will see a small fire by the door (the map and other related items are aflame), the door is simply locked from the inside, and the window is open. They have another chance to see the doppelganger in the room as a standard stealth check, disguised as the Innkeeper if he needed to get keys to unlock the door, otherwise disguised as the bugbear chief from the previous encounter. If they see the doppelganger as the Innkeeper, he will attempt to warn them that the Inn is on fire, then will strike with a surprise attack. If they fail to awaken, then one of the players will awaken to the first attack from an oddly dressed bugbear. The subsequent attacks will likely have advantage since the player will be unconscious and then prone. The doppelganger then flees out the window, and the party can either give chase, help their possibly downed ally, or stop the fire.
At this point, the players may take a single interaction to make sure that the door is unlocked for their party members to join, otherwise they have to succeed on a Strength 15 DC to break it down. A single player can also take their action to stop the spread of the fire. For each round that they don't stop the spread, it spreads. For each round, they do, it shrinks. Starting with the first round, a single player only has to declare that they are doing that as their action to completely stop the fire, otherwise it quickly spirals out of control and after the first minute the entire room is on fire.
The doppelganger may then return to the Inn as the dwarf and continue his rampage!
It sounds like an interesting scenario, you're giving them plenty of opportunities to catch wind of what is happening. My only thought would be to use a Con save for waking up, can't really perceive while you're sleeping :) Stealth/Sleight of Hand from the Doppleganger would be around 15 DC vs the players' Con to sleep through the disturbance, if you feel like giving advantage to the Doppleganger, then the DC could be that 18 you mentioned earlier.
The overall plan sounds ok. However, I would never let the doppleganger have a crit against the sleeping opponent since, from a player perspective, it is just too much of the DM just saying it happened and perhaps wanting to kill the character in question. The DM could protest that there were all of these dice rolls made that the characters failed but it is still, from the player perspective, just the DM whacking away on a character with an NPC no matter how good the "cinematic story" might be in the DMs head.
In addition, even in the way you have described it, it actually sounds like punishment to the player for the character actions taken in preceding encounters. It shouldn't be punishment for what you, the DM, might consider poor or rash decisions that should have consequences, it should be just the actions in the world playing out against the players responses.
For example, why is the doppleganger still with the party at all? Once they escaped why didn't they just leave? Why would the doppleganger have a map and why would he allow the players to commandeer it if it was worth anything at all?
If it matters to the doppleganger maybe they should just steal the map and put it in the fireplace at the inn.
Why would the doppleganger appear as a bugbear chief from a recent encounter? Didn't the party kill them off?
I'd also note that the 4d6 damage depends on the doppleganger actually having Surprised the opponent. Surprise is very restrictive in 5e. In order to be "Surprised" you need to be completely unaware of the opponent, not just unaware of their intentions. For example, if an acquaintance you were talking to suddenly decided to attack you might be surprised but not Surprised in terms of combat. PHB p 189. It is of course up to the DM and if the character is actually asleep when the attack happens then they would be Surprised but there would be a lot of checks getting to that point.
For example, kindling a fire in the room is VERY likely to wake everyone up. Even having someone enter the room might be enough to wake someone up unless they make a very good stealth roll. You also mentioned that there are two people in the room, the odds of entering, finding a map, lighting a fire, moving to the bed of one of the characters and then executing an attack without any of the rooms occupants noticing should be pretty small.
Also, depending on the circumstances, it could be very hard to notice a doppleganger. They will typically be getting advantage on all the opposed deception and insight checks due to reading minds AND they are proficient at both skills and even in they slip, they are likely to be able to recover. If the players have accepted the doppleganger as whoever they are imitating then they may not be making checks. On the other hand, the doppleganger does not have any memory, personality or mannerisms of the person they are imitating. Anyone who knows the person well is much more likely to notice or suspect something is wrong though if they don't know that a doppleganger might be involved then they might just think they are sick.
Anyway, in my opinion, No :) .. the scenario you outlined wouldn't be fair to the player involved.
David42,
The campaign is Lost Mine of Phandelver. The party was aware that Gundren Rockseeker was being held prisoner in a prisoner exchange. In the original campaign, the Drow simply wanted Gundren dead and to destroy the map, and the party would have had the opportunity to protect Gundren if they simply tried rescuing him. However, since they blockaded themselves in and took the short rest, I figured logically their lack of bravery would result in a negative outcome in the NPC death. Rather than having Gundren simply be found dead, I felt like it was more dramatic if the doppelganger took his place. The party had a chance to find Gundren's dead body but they missed it.
I made a bit of a logical mistake last session in which the doppelganger as Gundren revealed the existence of the map among his things, and tried to destroy it in front of them, insisting that he memorized the location and the enemy must not get it. Logically, you are right, if he didn't want them to have the map, he would have simply destroyed it when he hid the body.
However, since I already made this mistake I thought IF the party brought up the map, the doppelganger would discuss it with them in a misleading way while ingratiating themselves in the party, while attempting to steal and destroy it. If he can not clearly get at it, he will try to steal it at night, setting fire to the personal belongings and escape in the cover of the fire. He is a doppelganger and they are supposed to only strike when cornered, however an easy target could certainly be a legitimate goal. Maybe only if his plan is interrupted, he will surprise them from hide, running standard combat rules. To me, it is important though that he would do this only while the player is doing their long rest, split up from each other, and out of their armor.
Thanks for the clarifications.
I think I'd like to point out that by not finding a dead body, all the players think that they successfully rescued the prisoner and that there were no consequences to their short rest.They don't see anything dramatic ... only the DM does.
In addition, a short rest is only a delay of an hour. If the travel time to wherever they were going to rescue this prisoner was on the order of hours there is no real way for the players to know that taking a short rest would make a difference. Were the players clearly informed that every second counted and that a delay in getting to wherever the prisoner was being held of even a few minutes could result in the prisoner being killed? (I'm not sure if there is any way in game for that information to be available to them but if there is such a time constraint then it needs to be clearly and logically passed along to the players ... otherwise they go on the rescue mission with the fairly reasonable expectation that an hour is unlikely to make a difference in the outcome of the mission.)
Also, whatever you choose to do in your game is fine. However, after reading it over a bit ...
The doppleganger and the bugbear king Grol are negotiating. Grol wants to sell the map instead of surrendering it. This negotiation could take as long as you like. In addition, the doppleganger wants to question Gundren to find out if anyone else knows the location of the mine. However, Gundren is unconscious at 0 hit points in the corner of the room. It will take some time for him to wake up naturally so he can be questioned. Likely easily longer than an hour.
Also, keep in mind that the doppleganger doesn't know that Grol has hidden the map in the treasure cache under the mattress though he might be able to find it if given time to search after the bugbear is dead.
So ... I am guessing the characters invaded the castle and decided that they were too wounded (or had spent too many resources) to continue at some point and decided they needed a short rest?
If that is the case then I think you needed to make them realize that their actions had alerted all the creatures in the castle. If they take the short rest then either all the the remaining creatures will likely be positioned to kill them when the short rest ends or will have escaped and that their mission will be a failure either way.
For some reason the characters didn't realize that there might be consequences to the short rest. Instead, it sounds like they short rested then went on and killed Grol and rescued Gundren and his possessions. Mission accomplished! so the short rest didn't matter (as far as they are aware anyway). They then leave and Gundren realizes that he hasn't destroyed the map yet, pulls it out in front of the party and proceeds to try to destroy it. However, from the sounds of it the party intervenes and steals Gundren's map. Why did Gundren allow that? Did Gundren point out that it is HIS map and they characters have NO right to take it!? What reason did the characters give for not giving the map back to its rightful owner and instead putting it with their own stuff as if it was their map? Are the characters evil or chaotic neutral? Do they think stealing things from people is completely acceptable?
If the map is important then Gundren should get it back, throw it in the fireplace and leave before the characters figure out he isn't Gundren. However, if the map is important to continuing the ongoing plot then perhaps Gundren did a poor job of throwing it in the fire since he is in such a hurry. He threw it in a ball and instead of lodging in the flames it falls down the back of the burning wood where it singes but doesn't ignite. If the players learn its importance they can try retrieving it from the fire.
Finally, I just wanted to comment on the reasons behind this plot development ...
"I figured logically their lack of bravery would result in a negative outcome in the NPC death"
"if that player reaped what they sowed?"
"Essentially the party leader has made multiple back to back negative choices."
"She played it safe with their lives over a civilians while trying to raid a goblin hideout. Instead of executing a rescue on the civilian, they licked their wounds."
"She failed to either roleplay effectively or roll insight during the subsequent social encounters with the doppelganger into realizing the doppelganger was an impostor."
"The fatal encounter then occurs that is a waterfall of all her mistakes."
All of these comments make the planned game actions sound like a personal vendetta or punishment for the characters taking actions you didn't like or considered inappropriate or unlucky even if these actions may have been completely in-character for the specific character involved. DMIng shouldn't work that way. You control the world and how it responds to the player actions or lack of them, without getting personally invested. DMs enable the fun and adventure, but they don't police the characters choices of what they decide to do. Anyway, there are lots of ways you can run with this ... you might just want to consider your motivation and make sure that the NPCs are interacting as their character would tend to have them do and not in ways you want just to make life more difficult for the PCs.
Thanks for the detailed response David!
So basically, the party scouted with a Pact of the Chain Imp and discovered that Gundren was alive, and there was a negotiation over his release from King Grol to the Drow. They then decided to siege the castle from the front and successfully pushed the enemy forces deeper into the castle. They had a pretty good layout of the castle before even entering as the Imp passed its stealth checks to investigate so they knew what they were up against. The session ended and I refamiliarized them with the situation. That they should be aware that the Drow was going to take possession of Gundren immediately before the siege. I also made the character with the soldier background aware that while she has sieged a castle before, she is aware that they would likely fall back to deeper reinforcements and regroup for a pincer attack, and the best decision from her training would be to attack quickly while they were apprised of every enemy's position and the hostage situation. I also had Sildar warn them earlier that Gundren may already be dead, but he hoped that he was still alive. The party took their short rest yet blockaded their position, and while the goblins split their forces to prevent retreat, they failed to trap the party. I feel like I did not make the enemy forces overwhelming enough to properly reflect the consequences of the short rest.
"Why did Gundren allow that? Did Gundren point out that it is HIS map and they characters have NO right to take it!? What reason did the characters give for not giving the map back to its rightful owner and instead putting it with their own stuff as if it was their map? Are the characters evil or chaotic neutral? Do they think stealing things from people is completely acceptable?" This is a very good point. I felt like they thought Gundren was being rash. But yes, they essentially stole the map from him. I played Gundren as insistent on leaving out the secret entrance while the remaining enemy forces were regrouping. As soon as they tried grabbing the map from him, he relented as long as they agreed to leave immediately. So Gundren technically got part of what he wanted. I will definitely make this part of the roleplaying scenario next session.
"All of these comments make the planned game actions sound like a personal vendetta or punishment for the characters taking actions you didn't like or considered inappropriate or unlucky even if these actions may have been completely in-character for the specific character involved." So these choices were actually somewhat in character for her personality flaw, which is that she has survivor's guilt for a blood bath she was in, and no longer takes risks in battle. She is therefore, ruthless and would certainly execute a hobgoblin in a parlay, and would take a short rest to heal herself rather than risk hers or any other party member's life. She is also the one who explicitly stole the map from Gundren... she is technically Chaotic Good but I think she definitely shows shortsightedness and even evil tendencies in her character's personality.
I didn't want to 'punish' the player per se. If I did, I wouldn't have asked for advice on here, I'd have just done it! I did want to do something very dramatic so her character can realize that there are terrible consequences to her character's shortsightedness and flawed personality.