How do I prepare encounters for my party?

[Trandir]

Well, first time DM here and the party is now a bit emmmm... vulnerable.
I got:
Binder 3
Wizard 3
Warlock 3

All of them are rather squishy and I am a bit lost in how to build encounters for them.
Any advice is welcome

[Asmotherion]

Allow them to get (a) hireling(s) 'till about level 5. The point should be to get low level Fighter/Barbarian who should be able to tank without dealing lots of damage.

Though, the wizard does have access to some summons by level 1, and the Warlock can (if he got the right invocation) put the party in a safe bubble of Darkness 'till the Wizar's summon messes up the enemy, and then go for the kill. If they are more experienced players, they should be fine.

[Endarire]

What does each class like doing? You may have a crowd control-heavy Wizard who helps the group by making foes much easier to fight, thereby reducing damage to your party.

My solution as GM was a GMPC (that is, a GM-controlled party member that I made and played as if he were a normal character).

[Trandir]

Allow them to get (a) hireling(s) 'till about level 5. The point should be to get low level Fighter/Barbarian who should be able to tank without dealing lots of damage.

Though, the wizard does have access to some summons by level 1, and the Warlock can (if he got the right invocation) put the party in a safe bubble of Darkness 'till the Wizar's summon messes up the enemy, and then go for the kill. If they are more experienced players, they should be fine.

They are not experienced players, at all

What does each class like doing? You may have a crowd control-heavy Wizard who helps the group by making foes much easier to fight, thereby reducing damage to your party.

My solution as GM was a GMPC (that is, a GM-controlled party member that I made and played as if he were a normal character).

The warlock is blasty and got a cloud invocation, the wizard is a GOD type and the binder I have no idea honestly it does whatever that day's vestige tells and allows him to do.

Both suggest NPCs and I thought that was a last resort not the first one

[Endarire]

How do your players feel about having more GM-run people in the party? So far, your group seems fine, though low on healing. For the moment, I advise avoiding using ability damage creatures against your group.

[Trandir]

How do your players feel about having more GM-run people in the party? So far, your group seems fine, though low on healing. For the moment, I advise avoiding using ability damage creatures against your group.

And maybe other casters, or fey. Also are the shadows really CR 3 against them? Those things are probably gonna die before the first round ends

[Endarire]

Who goes first in an allip vs. your party scenario? If your Warlock goes first and hits with Eldritch Blast, you might avoid major ability damage to your party. Otherwise, what can your party do against this "CR3?"

[Saintheart]

In case it weren't already obvious, CR 3 is notionally (and wonkily, if not abysmally) balanced against a party of four characters. So an allip is notionally 25% more than the characters are theoretically designed for. On the other hand, if your players are not experienced, CR quite ironically tends more towards a decent warning system of what's too powerful than for the average seasoned grognard here and elsewhere.

That said, if they're squishy, then there's really two things to subtly or not-so-subtly point out and have available for them:

(1) They need to know when it's a good time to run.
(2) They need to understand that it's an option to run.
(3) They need to understand there's more than one way to win a fight.

D&D doesn't deal with the second point terribly well because the system has no real idea what to tell a DM faced with a party that rationally cuts its losses and decides to quit the field, or outright looks for a way to avoid the fight. As a consequence of a hundred little cues in the system, not excepting the XP And gold loss from failing to kill things, D&D encourages players to hurl themselves into suicidal oblivion. The murderhobo attitude, so looked-down-upon by so many, is nothing but a direct consequence of the basic structure of the average D&D adventure being one that George RR Martin must have been thinking about when he said in that in the game of thrones you win or you die. Encounters are conceptualised as roadblocks on the one road: either pass this fight, or you progress no further. That's what generates the death or glory mindset.

Point being, and this of course is going to be tougher since you're a first-time DM, but: if the group is weak but seems determined to climb every mountain, ford every stream, kill every monster until they find their dream, then you're going to have to get creative about how you build your encounters. One suggestion? Build load-bearing bosses. Every group of bullies has a leader; strike the shepherd, and the sheep scatter. If they figure out to focus their fire on one target which then ends the encounter if killed, that reduces squishiness. Another is just a flat-out morale mechanic: DC 14 Will save for any monster that loses half its hitpoints. Fail the roll, and the creature breaks and runs. Stuff like that.

[Nall21cp]

One thing you can do is think about environment and give them more options for using environment hazards or opportunities to ambush/surprise. If their initial ambushes fail to drop some meaty enemies, then they'd need to use environment for cover and/or escape.

Also make use of the world itself and social connections. My party regularly has guest npcs for one or two sessions due to their roleplaying influences on people and sometimes monsters. (Exp: they ambushed some slavers. The slaves got to help them fight once free)
(Exp2: they fed and animal friendshipped a wild and starving pair of tigones i had hunting them. They actually created their own sidequest to return the stranded "pets" to their half giant owner. Until then, the tigones were guest allies and it was hilarious to see them realize just HOW much trouble theyd been in if they had fought them)

[Biffoniacus_Furiou]

A guard dog that can trip opponents is 150 gp, and studded leather barding is only another 50 gp. That has a 19 AC and gets +3 to hit, if it's Magebred (ECS) and/or a Warbeast (MM2) it's even stronger and tankier. Each/any of them can take Wild Cohort to get one of those for free, and replace it for free if it dies (just buy the armor once, unless it falls into lava or something). You could just give each of them Wild Cohort as a bonus feat and they each have a character and a dog.

[Bucky]

If you're just feeling out what the party can do and don't want to kill them with unfairly hard encounters, just follow the guidelines for a 4-player level 2 party. That should give you some idea how much they can handle.

[Fizban]

The game expects a Cleric- and the lack of one will be a bigger issue than just how squishy the party may or may not be without heavy armor standing in front, since Binders can literally just call armor. Since you have not mentioned a significant replacement system for the Cleric, the solution is simple, albeit unsatisfying. You add one.

The main problem is that running a party member at the same time as the bad guys means you're taking even more of the turns, playing against yourself, etc. There is no good solution to this, since having one of the players play two characters isn't really fair either. Not from a spotlight issue, but rather, the only player who will likely be willing to track a Cleric's spells is the one who's already playing an actual spellcaster, which is the Wizard player. Who now has to manage both of the game's expected two full casters, while the rest of the party is on no-resource coast mode.

This is exactly what happened in my Red Hand of Doom game, and it was fine, right up until it wasn't- the rest of the party demanded forward progress at the start of a new session against the wishes of the caster player, and then that player's primary character got ganked while hiding at the back of the party and out of spells.

Otherwise, the best I've got is to get someone an Animal Companion. Make it a Warlock invocation, have someone take Wild Cohort, Wizard substitution feature, whatever. You'll still need the Cleric's status removal at some point, so an NPC that travels with them and stays out of combat might be a good idea, and without the Cleric's load of spell slots the party will remain squishy even if the Wizard loads up on all the protection spells available. Because contrary to popular belief, the Wizard is not god- the Cleric is the one who brings the god. Or sufficiently devoted belief system.

And maybe other casters, or fey. Also are the shadows really CR 3 against them? Those things are probably gonna die before the first round ends

Shadows are one of the particular standouts- not a problem with the CR system, but rather their placement within it. Even so, Shadows are entirely survivable if you have a Cleric. The standard expectation if the party meets something they can't fight is to run away, prepare new spells in the morning, and come back (and that the DM won't trap you in there to die or run them with Perfect Tactical Efficiency, obviously). Lesser Restoration is a 2nd level spell, so 3rd level is the minimum you'd want to introduce ability damage in any significant amount, and Good Clerics have Turn Undead. If you run into unexpected Shadows (or rather, one unexpected Shadow at 3rd), you either hope for a lucky turning roll, or just straight run away until it stops following. Then you heal up and come back with Magic Weapon and maybe Spiritual Weapon, which are yet more Cleric spells.

Incorporeal undead should not be used in numbers until 7th, when Death Ward is available. The Shadow is the weakest and placed at the lowest CR, the earliest point you can conceivably face it, but that doesn't mean you blindly follow the CR. In groups, they have some of the most disproportional PC kill ability in the game- which perfectly illustrates why if the DM actually leverages terrain and such to maximum effect, the PCs are expected to gain more xp from a fight than normal, and also how spellcasters "never running out of slots" is not meant to be true- as covering the whole party in Death Ward, Protection from Energy, Freedom of Movement, Neutralize Poison, etc can cost most of their slots.

The worst standout for messed up CR in MM1 is the Allip, which has ability drain and an action denial aura, also at "CR 3." That one's just bogus. Medusae are a fairly common complaint, but since a fighter can likely fight one to a draw with their eyes closed, not so much.

But, ironically, you're more worried about the Shadow dying too fast, ha. Don't forget that incorporeal creatures get a 50% miss chance even against magic if it comes from a corporeal source. The only thing they have that's a guaranteed hit is Magic Missile at ~ 7 damage per turn, vs ~19 hit points, assuming the "god" Wizard even prepared it.

[Yahzi Coyote]

(2) They need to understand that it's an option to run.

You've got to know when to hold 'em
Know when to fold 'em
Know when to walk away
And know when to run...

as any bard will tell you.

Seriously, though, running away doesn't work very well in D&D, which is a problem. You need to actively give your players a way to retreat because the rules don't support it. And a big shout-out to the morale roll; it's a great addition. One of my best sessions involved the players fighting to standstill and both sides deciding to negotiate because it looked to risky to continue.

[DrMartin]

Be upfront with your players - tell them what your concerns are, that they are playing the game with a class spread that is quite different from the way the game was designed, and they should not assume that every encounter is a fight, and that every fight is one they are supposed to win.

And after you have talked with them about it, reiterate that with every encounter: telegraph the monster way ahead of time, give them (the players, and the characters) clear clues about what's coming and how to prepare for that. Encourage them to look for information about the places where they are going and the foes they will encounter. And if they do look for those information - give it to them! don't be stingy. Give the players good hints and information, and let them come to clever solution about it.

You have inexperienced players, which is a blessing - they won't have many built-in habits and expectations. Let's say they have to trek from the Hamlet on the Rim of Civilization through the Swamps of Desolation to reach the Dungeon of Poorly Guarded Treasures, and they find out that the swamps are haunted by strength-draining shadows (seems to be a favorite from upthread). Let them hear legends about it from the townsfolk, and if one of the players ask you if there is some sage around who would know more about those creatures and how to thwart / avoid them - let there be one. Or maybe the Warlock asks his dark patron assistance or information. Or the wizard consults their books. You can even let them come up with a solution: "Wizard, your book has something about swamp dwelling strength draining magical shadows and how to fight them. What is it?" And then see where the answer lead you. "They can be kept away from the light of a fire lit by the innocent" - great, now they have to find someone innocent to light a torch for them and possibly accompany them during the trek. (I am assuming none of them is innocent here - why would they want to go to the Dungeon of Poorly Guarded Treasures otherwise).

Let them approach encounters like puzzles, don't be in a hurry to spring combats on them, talk to your players, and be generous with the in-world information you provide them. Fun games lie that way :)

[Fizban]

(1) They need to know when it's a good time to run.
(2) They need to understand that it's an option to run.
(3) They need to understand there's more than one way to win a fight.

D&D doesn't deal with the second point terribly well because the system has no real idea what to tell a DM faced with a party that rationally cuts its losses and decides to quit the field, or outright looks for a way to avoid the fight. As a consequence of a hundred little cues in the system, not excepting the XP And gold loss from failing to kill things, D&D encourages players to hurl themselves into suicidal oblivion. The murderhobo attitude, so looked-down-upon by so many, is nothing but a direct consequence of the basic structure of the average D&D adventure being one that George RR Martin must have been thinking about when he said in that in the game of thrones you win or you die. Encounters are conceptualised as roadblocks on the one road: either pass this fight, or you progress no further. That's what generates the death or glory mindset.

Seriously, though, running away doesn't work very well in D&D, which is a problem. You need to actively give your players a way to retreat because the rules don't support it. And a big shout-out to the morale roll; it's a great addition. One of my best sessions involved the players fighting to standstill and both sides deciding to negotiate because it looked to risky to continue.

What hundred little cues demand that the PCs stand and fight to the death at the first opportunity, how do the rules not support running away?

[Uncle Pine]

First off: you mentioned they aren't experienced at all, but how green are they? It makes a huge difference if they already managed to get to 3rd level as opposed to being handed or told to build a 3rd level character. The latter is something I personally don't recommend doing, especially as a first time DM, as class tables start from 1st level for many a reason, some of which include helping people get a grasp of what they can do one bite at a time.

Regardless, the following should apply:

1) Let them know of their "atypical" party composition, then embrace it.
Yes, the game allegedly expects each party to be balanced and include a mixture of meatstick, stealthy, and divine- and arcane-based spellcasters (these last two roughly translating to "healing" and "blasting with a bow"). However, this is simply one playstyle - and not even a particularly good one, as for starters dedicated healers are not a key role in d&d. Different group compositions can and should lead to potentially drastically different playstyles, as a big component of d&d is resource management and you cannot manage resourses you don't have access to.
To elaborate on this and before tackling the fact that d&d can be played with as low as one player (which in turn means having "only" three shouldn't be a major issue), let's examine a hypothetical scenario of attacking a bandit camp from the point of view of two atypical groups:

- "Oops, all beef": Fighter/Fighter/Barbarian/Paladin
With relatively large pools of hit points and equally large weapons, such a group may decide to simply barge in and butcher everyone who gives them a funny look. This doesn't necessarily imply a complete lack of tactics, as trip, bullrushes, and fear stacking are obviously welcome options and deciding to set the encampment on fire beforehand doesn't require specific class features. The presence of a Paladin means that there may be more healing available if the fight drags out (but see above) and/or mass buffs via spells or inspire courage to name a few.
All of this doesn't preclude more cunning options: smoking the bandits out of the camp or killing them in smaller groups as they patrol the area come to mind. It just means that if a big, long fight does happen the players should be able to endure and power through it.
In the future they may realise that certain opponents can't simply be killed with a greatsword in hand and your feet on the ground, but that's where magic items can help a huge deal! Buying casting of specific spells from an NPC spellcasters is also a possibility (see the Equipment section in PHB).

- "Easy peasy, lemon squishy": Rogue/Wizard/Archivist
You probably won't be seeing these three stooges charging towards the bandits head on. Not without a solid plan, or without dying horribly.
While this group has less members in it than the canonical four and no evident front-line character, it should by no mean be considered unfeasible or in need of serious handholding on the DM's part to be run effectively: just like monsters can prefer to ambush their enemies, so can the PCs. Rogues make great scouts and both Wizards and Archivists can provide a wealth of tactical information whether via Divination spells or Knowledge checks of various nature. Similarly, shaping the environment in both mundane and magical ways is a great tool to ensure you're playing on your own terms rather than the bandits'. They might even decide to entirely avoid direct confrontation and patiently gaslight the entire camp with illusions and/or stealth. Or, again, set everything on fire beforehand.
Does this mean that a direct confrontation between the stooges and the enemy will always end up in the former getting smoked in a couple round as the bandits tear through the little hit points they have? No, because twelve seconds of preparation is all our heroes need, for example, to go from no beef to two celestial bisons guarding their front.
On the other hand, it's entirely possible that such a group wouldn't last long if they decided to rest in the forest and a group of said bandits jumped on them in their sleep... but this is d&d! If you didn't plan for people jumping at you in your sleep, you likely deserved it.
In an average dungeon where mobility is an issue and information can be hard to come by, this could easily be the group patiently crawling through each room and square.

In both scenarios, the key message and road to success/survival is for each group to play to their strengths and try to cover their bases as best as possible. In most cases, running into a fight simply because the DM put it in front of you can spell doom even for the most balanced party. Therefore, don't do it.

But enough with examples.
Considering the wide versatility of both Binders and Warlocks, they can serve many roles up to and including melee ones (via Eldritch Glaive, for example). However, they also have great utility: in particular, binding Malphas is an amazing way to increase the chances that you'll fight on your terms rather than the enemy's. Once again, this significantly increase your odds of survival. A pure 3rd-level Wizard won't like seeing melee, but that's something one should accept when playing a 3rd-level Wizard.

With the above in mind, this looks like a group that wants to play smart rather than overpower foes through sheer numbers: while this is a discussion that can be had directly at the table, mid-session or even during session 0 as you're gauging and building expectations while setting the tone for the adventure and/or campaign, it's also a muscle that can be trained, for example, by populating the area around the dungeon or adventure locale with patrols, or by seeding random encounters before having them pop into existence 30 ft. from the party (both with rumours at the inn, or sounds or tracks in the forest, to name a few).

2) Adapt to your players' playstyle and group size. Mostly.
Three players are less than four. Quick Maths. In fact, a group of three 3rd-level characters is much closer in power to four 2nd-level PCs than that of four 3rd-level ones: the d20 Encounter Calculator can come in handy in these cases. This does not mean that you can't throw CR 3 enemies at them, it just helps to set what should be the base expectations of your group's power.

So, how do you build encounters for them players?
First off, what kind of adventure have you been running? A lot can be done to cater to a specific audience before even starting to populate the stage with actors simply by setting the stage properly: you wouldn't feed a scenario rich in intrigue, plotting and scheming to an "Oops, all beef" party, for example.
What's been your players' playstyle thus far? Do they not scout as far or often as their squishiness would suggest? If so, give them something in the environment to derive information from (i.e. tracks, carcasses, etc.). Even better have them be scouted by the enemies and, at least for the first time, have said enemy fail spectacularly: nothing spells "they might be out watching for us" like an archer hidden on a tree slipping and falling ball first on a lower branch in front of the players, loudly proclaming "****!" before breaking into a run for the bandit camp.
If you haven't at all started playing and you're just doing your homeworks, check the backgrounds of your PCs: what vibes do you get from them? There are several thick lines between "naive kid", "shrew and cold-hearted calculator", and "scorching rays akimbo". These are useful signals of what your players can expect to come, or even desire.
Provide options, sometime beforehand: encounters which can only be addressed in one specific fashion (i.e. this 10th level Big Bad Evil Guy whom you're supposed to fight only later and will kill you if you don't flee immediately) are a bad idea. This category includes hirelings, mercenaries and other critters like riding dogs: remember that for the average adventurer money is as much of a resource as hit points. A 2nd-level fighter mercenary is 6 sp/day. Raise Dead is 5,000 gp plus taxes. You do the math.

3) Just do it.
There's only so much prep you can do as a DM to ensure at the best of your capabilities that the adventure will go smoothly and a certain encounter won't wipe your party clean. Heck, that'll probably happen eventually, but as long as there's no malice on your part your players and friends will definitely accept the mishap and move on with a laugh. If you're still unsure about this whole situation, you can always google up a 2nd-level pre-written adventure (or "module") and run your players through it. That should give you a more practical example of the kind of shenanigans you'll eventually pull on your own behind the DM screen.

You might also want to keep in mind that while you should think through and plan most encounters to be sure you're not overpowering your players and killing PCs left and right, it is alright to occasionally throw balance out of the window (within reason) and go ham as long as you've been feeding appropriate intel to your players up to this point and it doesn't come out of the blue: I'd suggest to avoid random combat encounters with Large CR 9 black dragons for now.

As an example of this, a few weeks ago I was DMing for a party of four players whom I've recently introduced to the game. Composition: Beguiler, Fighter, Sorcerer, Soulknife, all 2nd level with none of them being particularly optimized, as they're new to it and I didn't want to overload them. At this point, they have six or seven sessions under their belt and entered a kuo-toa lair with the goal of exterminating them as they've been causing trouble to a village close to the coast. However, as they clear a hastily barricated tunnel they find themselves right into the kuo-toas' main sleeping chamber, with two kuo-toas right in front of them and two more reasonably close by (each is CR 2).
Initiative is rolled and while three kuo-toas stick to the combat, after only a few rounds one of them turns tail and flees into the tunnels. Three rounds later, it's back with a kuo-toa harpooner (CR 4) that was painfully familiar to the players after a brief skirmish they had with it one session prior, while the party was still looking for the lair. In the end, despite almost dying more than once, the party managed to prevail and survive, except they're all out and have to retreat to come back fighting another day (and session). For reference, four CR 2s and one CR 4 are a 7th-level encounter.
Was any part of this fight fair? Hell no. Would the players have been upset if they had lost one (or more!) characters in the encounter? Probably no. At this point they had spent several days scouting the area and facing kuo-toa patrols and ambush parties of various sizes, not always managing to kill all of them before they could flee. With that in mind, they knew there were going to be at least several specimens inside the lair (including the harpooner) and looking at their faces I could see that the possibility of failure and going out in a blaze dawned on them very early in the fight.
Would I recommend a fellow DM to plan out something like this in another situation? Maybe. Pitting a 2nd-level party against a whole tribe of CR 2 monsters is a huge bet, but I trusted my players to find a way through it and while worked*, I'll definitely reel in and be more conservative with my players at least for a few sessions after this ordeal ends.

Spoiler: *

Show

For now at least: they had the bright idea of retreating out of the lair and rest, but they've left a murderous kuo-toa whip with Water Devotion inside!
(spoilered because they'll find out about this next Tuesday)

[Saintheart]

What hundred little cues demand that the PCs stand and fight to the death at the first opportunity, how do the rules not support running away?

(1) Even if you get XP for "overcoming" an encounter by not fighting things to death, do you get automatic gold out of nowhere for "overcoming" said encounter?
(2) Can fighters operate with no gold and therefore no way of purchasing magic items?
(3) If (2) = "Yes, by killing things and taking their stuff", then see (1) and (2) again.

[Trandir]

(1) Even if you get XP for "overcoming" an encounter by not fighting things to death, do you get automatic gold out of nowhere for "overcoming" said encounter?
(2) Can fighters operate with no gold and therefore no way of purchasing magic items?
(3) If (2) = "Yes, by killing things and taking their stuff", then see (1) and (2) again.

Intresting points and if I where to see my party defeat encounters without killing them the missing reward from the minster's spoils would be found somewhere else. E.I. they have to get a McGuffin from a vault in an ancient city, if they manage to stealth and lie their way in they'd get extra loot from the vault

First off: ... Snap...

Well lot to answer.

They are 2 "never played 3.5" and one seasoned player (we lost another one that knew the game along the way).

The campaign is just at the beginning and it appears that it will be a light hearted adventure one, they got the guild to get the quests, lots of merchants NPCs, and they themselves have created emm... interesting characters: the wizard that wants to collect every single spell known in his spellbook (the most grounded one), the warlock who hates his patron and was basically forced into the contract, the binder who decided to fail all bindings checks to get a new personality each day ( and the player is having loads of fun with it). Also to make some context after the first quest they purchased a wagon equipped with a ballista to travel with stile and carry their loot.

So far their scouting has been nonexistent but we are just 4 sessions in so maybe they never got a "good opportunity" to do that so to speak

[Zarrgon]

Even with a "tough" group, the whole Encounter system is....weird at best. And anything can happen once the dice start rolling.

You might do well keeping the game more "groups of mundane foes" then jumping to shadows. Have 8 1st level warrior goblins instead. Or 8 warrior skeletons. Or even just 8 dogs. Or seven monstrous centipedes. Or have fun with things like one large animated object.

And have fun with say: a Medium Flame-Spawned Fiendish Dire Rat or small elementals.

Also you really want to add in terrain. Don't have fights in flat areas. Even just rocks and tress to climb can really change a battle. Not to mention deep water, fires, pits, logs and so on. Urban places can also have lots too them.

[Uncle Pine]

You might do well keeping the game more "groups of mundane foes" then jumping to shadows. Have 8 1st level warrior goblins instead. Or 8 warrior skeletons. Or even just 8 dogs. Or seven monstrous centipedes. Or have fun with things like one large animated object.

When creating groups, both large and small ones, variety can hugely and positively influence the excitement of the players. A single small change can be enough: make it seven warrior goblins and one adept or maybe seven warrior skeletons and a small skeleton dog, and watch the powerful effect such a tiny effort can have.

[Psyren]

The "GM's Guide to Creating Challenging Encounters" in my sig is a great read to help you with this.

[Zaq]

You're also in low-level territory where combat is even swingier than it is later on. So that's just something you'll have to deal with. I don't have a specific way of dealing with it, but it's good to be aware of it.

Overall, I think you'll be best served by encouraging your players to adopt a "fight smarter, not harder" mindset and getting them to realize (hopefully not the very hard way) that they might not want to always charge in head-on. The twin side of that coin, though, is that you should basically try to say yes whenever your players come up with a way of cleverly changing the terms of the encounter.

[Fizban]

(1) Even if you get XP for "overcoming" an encounter by not fighting things to death, do you get automatic gold out of nowhere for "overcoming" said encounter?

You may or may not get gold via the same method by which you overcame the encounter, obviously. If your only goal is getting loot, then presumably you don't gain xp unless you gain the loot. Neither of these prevents you from coming back better prepared to kill things and take their loot. If the party is "forced" to give up a bunch of loot, then it remains the DM's job to make sure they get sufficient magic items to meet the challenges presented, as it says in the DMG.

The presumption seems to be that if the players don't kill something on the first try, they can't possibly kill it? Which is false in a game that uses randomized mechanics, even before counting the players' ability to learn from their mistakes, and the variable nature of core problem solving classes that are literally designed so that you can come back more prepared. The only thing stopping them is if the DM designs the encounter to trap/pursue and kill them (which warrants an xp increase/bop on the nose for bad DMing because killing the PCs is not the goal), or if a single failure causes them to lose all hope and fight to the death.

The latter is sadly quite common, as are misunderstandings that lead to the former. But ultimately both are problems with the people, not the system. Only a pre-made module being run in a status-quo only game played by defeatist attitude players should actually have this problem. Even the possibility that video games have conditioned people to defeatist attitudes immediately rings false when the standard of video games is restarting from a save or checkpoint. The only difference is that in DnD you have to make a conscious decision to disengage, which can be communicated by saying "hey you don't have checkpoints so maybe run if you're losing?" Unless you just decide to run the game with "checkpoints."

I'm honestly kinda surprised no one ever seems to suggest that, going to great lengths on how important investment in characters and story is and how you have to git gud and build builds, then effectively saying that the game must be run as the world's slowest Roguelike with zero chance to learn from critical mistakes. If your players don't know 3.5 and screw up and get TPK'd, just say "Wow that was a bad run, let's try again shall we?" and start the fight over. Actually getting to fail and then retry the same fight and learn something will get better results for figuring out how to get this party through fights than basically anything else.

But yeah. You said a hundred things and listed one. Does Yahzi have more detail? I was expecting at least some complaints about AoOs (which is why the Withdraw and Full Defense actions exist), or monster speed vs armored PC races (which demonstrates why many adventures and monster descriptions will call out that the monster does not pursue fleeing characters), or lack of examples (when many monster and NPC descriptions in published content have the bad guys flee at low health).

[Doctor Despair]

The latter is sadly quite common, as are misunderstandings that lead to the former. But ultimately both are problems with the people, not the system. Only a pre-made module being run in a status-quo only game played by defeatist attitude players should actually have this problem. Even the possibility that video games have conditioned people to defeatist attitudes immediately rings false when the standard of video games is restarting from a save or checkpoint. The only difference is that in DnD you have to make a conscious decision to disengage, which can be communicated by saying "hey you don't have checkpoints so maybe run if you're losing?" Unless you just decide to run the game with "checkpoints."

I'm honestly kinda surprised no one ever seems to suggest that, going to great lengths on how important investment in characters and story is and how you have to git gud and build builds, then effectively saying that the game must be run as the world's slowest Roguelike with zero chance to learn from critical mistakes. If your players don't know 3.5 and screw up and get TPK'd, just say "Wow that was a bad run, let's try again shall we?" and start the fight over. Actually getting to fail and then retry the same fight and learn something will get better results for figuring out how to get this party through fights than basically anything else.

If they wanted a RAW mechanic, I guess the DM could give them some sort of custom artifact, or a blessing from a deity of some sort, that confers the mechanics of Teleport Through Time using that checkpoint method. Completely busted mechanic from a TO standpoint, but I'm sure this party won't abuse it to any significant extent if they're relatively new to the game.

[Trandir]

If they wanted a RAW mechanic, I guess the DM could give them some sort of custom artifact, or a blessing from a deity of some sort, that confers the mechanics of Teleport Through Time using that checkpoint method. Completely busted mechanic from a TO standpoint, but I'm sure this party won't abuse it to any significant extent if they're relatively new to the game.

Or just resurrect them at no cost and no drawback and they have to get their gear back. Fun little sidequest or player's worst nightmare. Depending on who you ask

[Psyren]

You don't have to rewind either, if explaining that would be a pain point or ruin tension or break immersion. When they "die", you can simply cut to black and have them wake up in a dungeon or temple or hospital etc. You can do this even if they hit the "-Con" threshold. Then have whichever NPC(s) rescued them stroll into the room bearing a fresh bundle of plothooks.

[Nifft]

1 - In ye olde school games, overcoming an encounter MIGHT include murdering the enemy, or it might include distracting / tricking / scaring off the enemy and then running away with all the loot.

2 - If your players can spec for trickery or stealth, having a small lightly-armored group becomes an advantage: fewer Move Silently checks => fewer natural 1s. This gets even better when you can scout reliably, with a familiar or a Vestige ability.

3 - With a smaller group, you can spend more time on each player's actions. Illusions could be described in detail, and winning an encounter with one spell is proportionately less horrible when you're stealing spotlight from fewer players. (Don't let this happen too often, but once per session seems reasonable if the other two PCs get more spotlight time in other encounters.)

4 - Cross-country travel might be doable with them as the high-priced specialists, and a group of ~8 level 2 NPC Warriors as guards. The sponsor might pay them a bonus for each guard who survives the trip -- they're motivated to save the meatshield resource, but it's less important than their own lives.

[Bucky]

This sort of party lives or dies based on its battlefield control and positioning decisions. That means you should build your encounters with that in mind.

Give the party the space to move around; they shouldn't start a fight with an enemy in each player's face, nor should they start the fight cornered with nowhere to move to.

At the same time, give them actual terrain features to work with. Free-standing obstacles, patches of difficult terrain, cover. A complex battlefield gives them more opportunities to cleverly position themselves, and their spells.