Encounter/CR Rules An Artform

There seems to be some 4e partisanship going on in your response that makes a ton of assumptions.
Well, sure, go right there whydontchya? ;P

I'm very much a D&D partisan*, but credit where it's due - and where goals & objectives are met.

5e's goals did not include "improve the dependability of CR guidelines." I mean, they may have been down there on the priority list somewhere, but, you can't blame a design for doing something only moderately well that it wasn't much trying to do, at all...

For example, with respect to Theater of the Mind, most of the 1e/2e play that I did used TotM as well
I hear that now and then. I suppose that might've caught on sometime in 2e, when that ed was aping storyteller, but 1e & 3e, generally tended to use minis, one way or another, IMX. We all just have had different experiences, especially "back in the day."

I mean seriously, you wouldn't expect a 1e table accustomed to assume TotM play to nonetheless assume combat continued to function as normal if a Paladin in platemail fell into the salty sea while battling a squid.
I would not expect a 1e table to be accustomed to TotM play, period. Like I said, different experiences.
1e did have some quite detailed, perhaps a tad merciless, rules on underwater combat, though, that's a rather extreme example of 'terrain.'

There would be certainly assumptions made about the ability of the Paladin to move in this new environment - to say nothing of breathing in it
Nod. OTOH, he's been grabbed by a giant squid, he won't be doing a lot of moving, anyway. (Ironically, the deadliest thing the squid might do is let the paladin go - some 1e DMs just loved drowning characters in heavy armor.)

TotM tends to shake out like that, the things it doesn't handle get ignored. 5e CR guidelines double-down on that, a bit, because TotM works most easily with few enemies or reasons to move around, and 5e CR works best for few (or one) enemy, too. The path of least resistance in the default mode is simple encounters with lone monsters.

As for the assignment of CR, 3e, Pathfinder, and 4e all had monsters which were notorious for being harder than their CR suggested
At the risk of sounding "4e partisan," again, the notorious 4e monsters in question were in KotSf and the MMI, and the latter were errata'update'd. ;) I'm unaware of any issues with CR in PF.

And as far as I can tell as an outsider, 5e has continued this with several monsters being much harder than their CR would suggest - ropers, magmin, intellect devourers, shadows, zombies, etc. So when I say that the CR is wrong, I mean 'wrong' in a very literal sense that the wrong number was probably assigned to the CR.
I can't say I've seen a lot of that. I've certainly seen combat go much harder than intended, but it's not typically just the one monster CR that's at fault. It's numbers telling heavily due to BA, or the party not having the right composition...
...and it's prettymuch limited to the lowest levels. After that 5e seems to break too easy a lot more than too hard.

* But there was no partisan, nor spetum, in 4e, or 3e for that matter - Ransuer was the closest equivalent, IIRC. You gotta go back to AD&D for the cool polearms.
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@Zardnaar The titanoboa played great – definitely on the more dangerous end of the CR 12 spectrum, so good for experienced players. I've been contemplating using a Possessed Pillar vs. Clay Golem in an encounter. The possessed pillar is great for foreshadowing magnet-based traps or hazards in a dungeon, so for my purposes with Tomb of Annihilation (where there's one or two significant magnet-based traps), it's a great fit. Overall, I've found Tome of Beasts to be a great resource, though as @Celebrim points out in his excellent analysis, like the Monster Manual you do need to approach CR ratings with a grain of salt as there's substantial difference between monsters of the same CR.

@robus What is playing at 19th level like for your group in 5e? You said you throw out all the encounter/adventuring day guidelines and just follow your gut / whatever makes sense in the narrative? I've never played or DMed that high-level. My groups always seem to cap out before 13th level. So extreme high-level play is a mystery to me!
Oh, even more generally: running 3e or 4e may have had elements of science - rocket surgery even - to them, but running D&D in general, the classic game & 5e, always more Art.


Lowcountry Low Roller
@robus What is playing at 19th level like for your group in 5e? You said you throw out all the encounter/adventuring day guidelines and just follow your gut / whatever makes sense in the narrative? I've never played or DMed that high-level. My groups always seem to cap out before 13th level. So extreme high-level play is a mystery to me!
It’s been interesting. Fortunately my group likes the exploration side of the game a lot, so just throwing a new location at them makes everything feel fresh. They find political intrigue very boring so all the talk about high level players needing to build kingdoms etc doesn’t fly.

I did have to blow up my high-level remix of OotA as there just wasn’t enough variety for their exploration needs to be met. Probably my inexperience as a DM was a factor there, but it just all seemed quite samey.

The game has gotten a bit gonzo as I now throw whatever I like at them but that’s made it fun for me and they have no idea what’s around the next corner.

Of course I had a lovely bit of mystery/exploration set up for them in the last session, but they managed to get a very useful clue right from the get go that kind of led them through things but they enjoyed it all the same and felt pretty clever in the process :) Next they’re going to go on a epic level 20 quest to a totally new plane (ancient greek aesthetic) where they will be searching for the lost Temple of Platanos and the Sphere of Tranquility that lies within. Various mythical beast encounters and strange peoples will of course lie along the path to make it interesting.

I would like to get them to use the alternate resting rules for the journey, but as they have various portable shelters it seems hard. I would like to say that they gain the benefit of a long rest whenever they visit a temple, but not sure how to pull it off. I may just ask them if they’ll go along with it... they’ll probably say yes as it will encourage exploration :)

So, I’m sure it really depends on the group and what is fun for them but now that I’ve taken off the training wheels (i.e. running 100% custom content and throwing caution to the wind) I’m having fun and the group is too.

I just realized that we’re about to come up on our 4 year anniversary of the start of this campaign! Seems like a good time to be bringing it to a close.