D&D General Playing to "Win" - The DM's Dilemma

Every DM has their own perspective on this question: do you play the monsters to win?

The thread about how often a PC death "should occur" has had myself thinking on this for a while now. I know, as DM, I can throw whatever I want at the PCs, and while I don't think success should be guaranteed to the players, I do feel the point is generally to make certain they have a fighting chance--perhaps even a fair one on occasion. ;)

But how cunning and resourceful should their opponents be? What lengths should they be willing to go to defeat the characters? (dependent on their personality, alignment, behavior, morals, etc. of course)
My answer: whatever lengths makes sense for that creature.

Mindless zombies aren't going to do anything tactical or strategic. They're nothing more than self-propelled punching bags or target practice unless the PCs are abysmally stupid.

The stereotypical Evil Wizard, on the other hand, is going to do whatever's in his power to deal with the threat posed by the PCs, once he becomes aware of it. Note however that "deal with the threat" can take many forms, from outright killing to capture to charm to diversion to etc. For example, to temper their threat against him he might have an agent recruit the PCs to deal with some other adventure instead, in hopes that other adventure does them in while leaving him an avenue of plausible deniability.
How much foreshadowing should the DM feel necessary to warn the players, "Hey, this is going to be a tough fight, perhaps a TPK, so I'm giving you hints of a warning here..."?
Situationally dependent. If they've been cautious and-or done some scouting and info gathering, foreshadow away and give them ample warning; but if they just face-charge in without a second thought then they're yours to kill as you please. :)
While "not fun" for the player in question, one tactic is using magic or terrain to isolate one PC from the party; either to deal with that character or remove them from the battle while the other PCs are dealt with. This typically greatly increases the monster's chances of defeating the party (the "win").

Another strategy is using a familiar or similar creature or magic to spy on the PCs to observe their strategies, strengths, and weaknesses. This allows your monster to gauge which PC is the greatest threat and in what fashion, so they can counter the PCs as well as possible.

When the adversaries are multiple casters, such as a Hag Coven, this creates situtations which some players might feel are "unfair" and certainly "un-fun".
Tough. That's what you get for taking on powerful people (and, mechanically, is part of why those powerful people are worth so many xp and-or carry such a high CR).

The way I see it, if the PCs can do it then - given the right circumstances/equipment/abilities - so can their foes. A Hill Giant isn't going to use a crystal ball to scry on anyone but a spellcasting Vampire sure could - if she had one. If the foes are known to have any Druids (Nature Clerics) among them then the players know any animal or bird is to be treated with suspicion because their own PC Druid uses shapeshift for spying and scouting all the time. If the foes have long-range Clairvoyance and can target a PC then why not do it?

Note that the same restrictions apply to the foes, of course, as to the PCs: for example if the foe has never seen any of the PCs then any scrying the foe has can't be used on them.
For myself as a player, since I often DM, this has never been an issue for me. And while I feel a primary goal of the game obviously is for everyone to have fun, I sometimes find myself at odds because what is fun for myself as DM is a believable world which challenges the PCs, not a game where the players just get to enjoy themselves and "win" all the time.

The last thing I enjoy and very rarely ever do is bail the players out of the situation. I try to give them warning, the chance to learn what they can instead of just charging blindly ahead, retreat (to a point---sometimes you are just in too deep!) and regroup, etc. but if they fail to take advantage or think of such things for themselves, I often feel like they have no one to blame but themselves.
That's where having an NPC adventurer in the party can be a real help: the NPC bailing out is a pretty good clue that the PCs should probably follow suit. :)
I know the battle looming ahead for my party looks bleak for them from my point of view. While well-equipped and working well as a team, I see the potential for a TPK, particularly if I separate the PCs from one another and deal with them as smaller units instead of a whole group.
I've got a similar one coming up soon (i.e. we ended last session on the cliffhanger leading into this encounter) - I-as-DM know that between their items and abilities they've got the means to potentially deal with it with only low-to-moderate risk but if they don't think to use said means and instead try something else they're probably hosed before they start.
Weeks ago, I posted about the dragon encounter the PCs faced. Even though only 7th level at the time, the managed to "fend off" an Adult Black Dragon (CR 14), at the loss of a party member. Through some luck and planning, they managed to avoid the second encounter as the dragon hunted for them after resting. So, perhaps this encounter will go better for the players than I am imagining. We'll see.
That's the thing: parties - as opposed to individual characters - can be surprisingly resilient things provided they're willing to use their exit strategies and getaway cars.
 

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Sure, obviously you need to make it a fair, rational challenge. (Or telegraph heavily that the players are in way over their heads.)

I'm just wary of the mindset that I've seen of "If you're not using RAW monsters, you're not being fair." Not common, but an opinion I've seen expressed in the past.

Well, that's absolutely not where I'm coming from, to make it clear. I just think you need to be mindful of the difference in effect of what you change.
 

Maybe we can talk about an example and folks can use it to illustrate how they prefer to do things. I will use a real world actual play one.

In a dungeon, two PCs wandered off on their own to scout while the others short rested (I know, I know, but they wanted to). They ended up encountering a hungry grick, which attacked. By some luck, the thing dropped one PC to 0. I decided to have the grick grab the PC and retreat to its lair to eat the PC, becuase it was a hungry predator. The other player ran and the captured PC was devoured.

Would you have done it differently?

I don’t know all the details but usually a list of random encounters is either A) geared toward the PCs level to some extent or B) setup in such a way that PCs can avoid them.

Which highlights the problem of splitting up. Random Encounter difficulty isn’t actually random, it’s targeted around an average difficulty level based on the whole party. Split up and your party and you are nearly always going to be outgunned.
 

Like focus fire. That’s the only tactic I’ve explicitly mentioned thus far.
If the foes decide for whatever reason to spiral on one PC it means they're not hitting the others, and while that one PC is probably in deep trouble the rest can - one hopes - deal with the foes and then cure or revive the one who got spiralled on. Archers vs backline casters is the obvious example here.

For big dumb single opponents (e.g. Hill Giants or Ogres) my usual go-to is they exclusively attack the first melee foe to hurt them unless another character hurts them more. So if Bob the Ranger happens to be the first PC to hit and hurt the Ogre in melee the Ogre's going to spiral on him until one or the other is down; but if Jocasta the Fighter then comes in and lays a smackdown critical on said Ogre its attention will quickly shift to her instead.
 

If the foes decide for whatever reason to spiral on one PC it means they're not hitting the others, and while that one PC is probably in deep trouble the rest can - one hopes - deal with the foes and then cure or revive the one who got spiralled on. Archers vs backline casters is the obvious example here.

For big dumb single opponents (e.g. Hill Giants or Ogres) my usual go-to is they exclusively attack the first melee foe to hurt them unless another character hurts them more. So if Bob the Ranger happens to be the first PC to hit and hurt the Ogre in melee the Ogre's going to spiral on him until one or the other is down; but if Jocasta the Fighter then comes in and lays a smackdown critical on said Ogre its attention will quickly shift to her instead.

None of that sounds like ‘playing monsters to win’
 

I don’t know all the details but usually a list of random encounters is either A) geared toward the PCs level to some extent or B) setup in such a way that PCs can avoid them.

Which highlights the problem of splitting up. Random Encounter difficulty isn’t actually random, it’s targeted around an average difficulty level based on the whole party. Split up and your party and you are nearly always going to be outgunned.
Depending on where you are. In dungeons (which is where this was) it is based on "dungeon level" which is only analogous to PC level if the players decide it is. In the wilderness, it is based on what lives there.

APL based encounter charts are an abomination.
 

Because if the DM regularly does even basic things like focus fire PCs. Not pull punches. Etc. These are things the PCs have no or very limited defense against. Some of them will die and since they have no in game recourse to prevent it then the loss will feel and be unfair.
The PCs have many defenses, not least of which is to avoid those situations in the first place when-where possible.

Invisibility, defensive spells, improved strategies, using stealth to catch the foes off guard, focus-fire of their own, etc. etc.

And yes, some of them will die. The only time it might feel (and in some cases actually be) unfair is if-when the DM spirals on the same player's PCs all the time rather than spreadin' the love a bit.
 

None of that sounds like ‘playing monsters to win’
In the case of intelligent foes, spiralling on one PC at a time is playing to win...just the same as when PCs do it to the foes.

In the case of big dumb brutes there's no "play to win" there, it's more a matter of the creature "playing not to lose" and lashing out at that which has hurt it.
 

Sure, I agree that monsters should use whatever tactics are available to them to try to achieve their goals, which in this case I would assume is protecting their lair from the invading adventurers. But, the thing is, using Wall of Force to split the party isn’t a tactic that’s normally available to green hags.
Which I see more as a failing on WotC's part. The Hag Coven spells rely too heavily on divination and enchantment-type magics IMO.

Wall of Force is simply one of the best spells at 5th-level for crowd control IME.

For what it's worth, a quick scan of monster in 2014 have only five creatures with wall of force as part of their default spells. Lich is NOT on that list, which I find surprising.

Abjurer
Alhoon
Archmage
Blue Abishai
Mind Flayer Arcanist

This isn’t a matter of playing the monsters to win using all the tools at their disposal, it’s a matter of giving the monsters a new tool so they can win more easily. That, to me, is a significant difference.
I mean, for the same 5th-level slot I could upcast hold person and target all 4 PCs, likely getting two or three of them, and then lightning bolt or fireball for auto-failed saves by both the other hags. That is about 65 damage (we use exploding critical damge) to each PC who fails against the hold person--two PCs in particular if they fail vs the hold person would be dead since their HP are below 65.

I mean, a lot also depends on initiative, etc. when the fight starts, but even without wall of force it can be a scary encounter. I would be replacing one of the two diviniation spells (in this case contact other plane) for wall of force.
 

Sure, obviously you need to make it a fair, rational challenge. (Or telegraph heavily that the players are in way over their heads.)

I'm just wary of the mindset that I've seen of "If you're not using RAW monsters, you're not being fair." Not common, but an opinion I've seen expressed in the past.
For sure. Yeah, I’m not at all opposed to modifying monsters or using from-scratch homebrew ones. I just think that, especially when modifying monsters, it’s important to consider the players’ perspective and ask, will this feel more like a fun challenge or a screw job?
 

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