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Dretches and Lemures.
Can you imagine the misery?
It's those sort of things, the lost and the irredeemably damned which give me shudders. Allips and Banshees and Ghouls too.
All the things which were people with minds, hopes, dreams, love... now all gone. No salvation for them. And there but for the grace of [Iomedae] go I...

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Second edition slimes really unnerve me. They'll drip down into someone's neck without anyone noticing really, numbing the skin and infiltrating the body. A couple of hours later one of your party members has turned into a slime creature and he's creeping up on you.
I have a "soft spot" (as in, am easily scared by) monsters that somehow "infiltrate" - like skin-burrowing parasites, or bugs that'll crawl in your nose and ears.

lemeres |
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Pugwampis. F%~#ing pugwampis.
No, use the proper term for them:
"45' across circles of no save, automatic, AoE misfortune hex".
Giving those things class levels so they don't die in 1 hit seems like the scariest thing you could throw into an encounter. Imagine if they ever teamed up with kobolds?
They are why the 'trap' option of the First Worlder archetype summoner could cause the GM to pull their hair out just as much as a beasted out eidolon or a Master Summoner horde. If you can work the rest of the party around the one escape clause of 'luck bonuses cancel it out', at least. But even without that, the party wizard could do some devastating Save or Die spells.
But Shadows and Shadow demons are close in there for me, since they are incorporeal and have nasty abilities (heck, the shadow demon is partially balanced due to a weakness to sunlight, which the GM can completely deprive you of with 'it was a dark and story night')

Aeander |
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Witchfires.
High AC, incorporeal, invisibility at will, flight, very strong touch attacks, faerie fire and fire vulnerability when hitting or hit. These things are ridiculous at their CR.
If a character of mine saw one of these emerald infernos they'd either unsling their ghost touch longbow or assume the fetal position and hope for a quick immolation.

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I don't know about in Pathfinder.
Back in the good old days, it used to be hands-down the rust monster. Never did you see more armor-wearing titans of death piss their iron shorts, scream like little girls, break into a cold sweat, run for their lives and hide behind the (figurative) skirts of the party wizard and thief than when one of those innocuous little beasties approached.
This
For most parties, rust monsters inspired sheer terror unlike anything else in the game.

Dreaming Psion |
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The Tooth Fairy. It scared me as a kid and still scares me as an adult.
Are you talking about the ones in Bestiary IV? ;)
From an encounter, the other day, groups of cairn wights. NASTY, NASTY, NASTY level drains. Give 'em bows and they're even MORE nasty!

Ciaran Barnes |

The only time I've seen a group of grown men's player characters turn tail and run at the mere sight of a monster was when an underdark beholder floated 'round a corner while we were mopping up his minions. We didn't know they were minions at the time, and every single one of us was off the combat matt in one round. There was no discussion or tactical withdrawal, just full-round withdraw actions. This is of course due to each of us growing up reading about legendary monsters like this one, and never actually having to face one until then.
In Pathfinder though, I can't say I've experienced anything quite as dramatic as this. In Kingmaker, which my former group played from 1st to 10th level, there were a couple of fights we ran away from, and a couple of others I wish we had.

Dreaming Psion |
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Although I've never really used them, my players mistaking some villager descriptions of aberrations in a nearby dungeon made the players nearly crap a collective brink. And then a sigh of collective relief when they found out the aberrations in question were not rust monsters.
I guess even sight unseen some monsters can build up such a reputation that they can make even hardened characters quiver in their boots like timid schoolchildren.

ParagonDireRaccoon |
The monster I've gotten the most mileage out of over the years for scaring players is the mimic. I used to include at least one mimic in every adventure, and completing the adventure became a secondary objective to killing the mimics (I would advance their HD as needed). I once had seven mimics disguised as chests, each smaller than the last, inside a regular chest. The PCs did every check they could think of on the outer chest, then removed each chest after that without checking.
The monster that scared a group the most was a pixie cleric. Early in 3E I ran for a group that was mostly rogues. I gave them an NPC pixie cleric named Blixina (think Tinkerbell as a healing/support cleric). One day they returned home with Blixina only to find their Blixina bound and in a cage- they were twins, and I had decided pixies give twins the same name. The players realized they now had no cleric, and had to fight a cleric with minions (also waiting at their place).

aceDiamond |
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Ladies and gentlemen, I present the Drakainia. If you don't take real life SAN damage after reading "Invert Birth", I don't know what will phase you. Plus, the artwork in the Bestiary 4 is horrifying.

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Ladies and gentlemen, I present the Drakainia. If you don't take real life SAN damage after reading "Invert Birth", I don't know what will phase you. Plus, the artwork in the Bestiary 4 is horrifying.
Pretty sure Darakania is the most difficult monster in all of the Bestiaries that isn't a Great Old One, right? And even Great Old Ones don't have Mythic Ranks. (shudder)
For low level, though? Stirges. Just . . . freaking Stirges, man.

Shasf |
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The scariest monsters are the ones you cannot see.
Though my players seem to have a great dislike of kobolds and glue pots/tanglefoot bags. They made a song about it.
Though now I think I shall introduce them to pugwampi's and glue pots/tanglefoot bags... adding in class levels too. Maybe a pugwampi with a grease spell.
Though the scariest monster that I've run was a human child ghost, wielding a ghost touched dagger, it sang a lot as it chased the party through a sewer with tight spaces for medium creatures.
Good times.

Third Mind |
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For me it's almost anything that turns you into one of them. Vargouilles for instance (spelt that wrong I know it) are terrifying in how they turn people.
Also those hood things that drop from ceilings and envelope you head. Executioner's hoods I think they're called. I just imagine all that stuff and it'd be terrifying to me.
That said, it makes me wonder how many players would roleplay their PCs as freaked out of these things. Mostly I tend to see characters (including some of mine) sort of not react in fright almost ever. I guess they are the heroes though. Can't be looking like a scaredy cat.
Edit: Also, at low levels, wisps. My wizard refuses to go to an area he knows is infested with them.

Caimbuel |

A Mystic Theurge wiz/cleric at 20 with 19 caster in wiz, 11 in cleric. Then you can cast all those divination's to be batman with I win buttons on the party. Hugely unfair in some cases, chump change in others, but sure said wizard has a lot of summons and bindings when the party shows up. And if it is evil you could have some dominated meat shields. Play the supper smart BBEG as bad as ya want, depending on players they can probaly answer, but they sure will remember.

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For my 3.5 favored soul? Skeleton archers, all five time I EVER played one, my dm would have us eventually encounter skeletons. Rolling the dice in front of me, rolled triple natural 20s for an instant kill (house rules we used at the time, and still do when it comes up)
For my 3.5 samurai? Tables, no joke, got the same instant kill result from an animated table.
Really turned the tables on you hunh?

Tacticslion |
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Giant Spiders. Nope nope nope nope. I mean seriously. A spider larger than you pinning you to the ground under it.
Scavion! I've got a present for you! It's not even exploding runes!
(You are guaranteed not to like this present.)
((I.e., "Yo dog, I heard you like spiders, so I put some spiders in your spiders."))

Dreaming Psion |
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For me it's almost anything that turns you into one of them. Vargouilles for instance (spelt that wrong I know it) are terrifying in how they turn people.
Vargouilles can be particularly harrowing because if they pucker up and kiss you, you're living on borrowed time if you don't have a cleric with remove disease prepared (or light spells etc. to delay it). 24 hours is almost enough for you to go through the 5 stages of grieving several times over.
This happened once to a beloved (by the player, not so much the other PCs...) halfling bard who was paralyzed by the horrid things screech and then got that horrid smooch. He was getting far enough into it that his hair fell out, his ears turned into batwings, and he grew chin-tentacles. (Of those, the loss of his hair was the worst because he spent so much time and effort grooming it- he even slicked it back with gel).
Sadly, the full transformation did not make it through- they had to ally with the kobold healer who cured the affliction.

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My vote for scariest goes to Derro. They have "shadow communities" underneath just about every major city, they sneak into your house and steal you out of your bed at night when there's nothing you can do about it, and they "experiment" on you for unknown reasons. Usually these experiments erase your memory of the abduction and then they bring you back, but on some level the mental scars are still there, along with the results of the "experiment". And then sometimes they DON'T erase your memory. And sometimes you DON'T make it back.
Mechanically, they're everything that's frightening about gnome or halfling sorcerers, plus they use their Charisma for Will saves instead of their Wisdom. Also any group of them is bound to have a guy whose weapon can trip you from 20 feet away.

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My vote for scariest goes to Derro. They have "shadow communities" underneath just about every major city, they sneak into your house and steal you out of your bed at night when there's nothing you can do about it, and they "experiment" on you for unknown reasons. Usually these experiments erase your memory of the abduction and then they bring you back, but on some level the mental scars are still there, along with the results of the "experiment". And then sometimes they DON'T erase your memory. And sometimes you DON'T make it back.
Mechanically, they're everything that's frightening about gnome or halfling sorcerers, plus they use their Charisma for Will saves instead of their Wisdom. Also any group of them is bound to have a guy whose weapon can trip you from 20 feet away.
Have you been watching Dark City again?

Kayerloth |
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It's rare, but a good GM is the scariest thing.
and similar posts above
Combined with something you've never encountered (neither in nor out of character)
Nothing is quite as scary to my mind as the unknown. Imagination runs wild especially with a GM who you know likes to create stuff.
edit: Reminds me of my players reaction when "the creature" chased them out the postern gate, which they slammed shut, only to watch as the door first smoldered, then charred, the burst into flame as the creature came through the door at their badly injured party ... nothing says fear like an entire group of players rapidly and desperately searching character sheets looking for something, anything to try and slow down much less defeat the unknown apparently invincible foe coming at them.

Daenar |

Heh. A bad DM who thinks he's a good DM. Cannibalizing previous editions , radically house ruling on the fly to suit his/whims and all in the name of adjusting for character power. In no way meant to be gm vs player, overpower encounters or other wise give high stat arrays to PC's only to have them feel gimped anyway because all the monsters are tweaked out on DM roids. Yeeaa , love that homebrew.
All of the above is sarcasm for readers only perceiving literal wording.

Emmanuel Nouvellon-Pugh |

^Daenar is my soul brother
For me it's the Medusa.
GM sends 6 at us with flaming seeking longbows in a long trapped narrow hallway.
As soon as we enter 30' there's only a matter of time until someone rolls a 1, and then one swings out an adamantine mace.
The worst part was that they were "clones" in that they had no different stats, player levels, and the GM BS'd that a player cannot avoid a trap they see triggered even though that is the entire function of a 10' pole.
An encounter in AD&D in the caves of chaos had a room where if you ran in you were turned to stone without a save. This was fine since the medusa was tied up and other players were forewarned by this petrification. A successful negotiation also grabbed you 6 droughts of stone salve.

Proley |

Wights.
1 wight and two zombies against a 4 man party overtime became a 2 man party v. 1 wight and two zombies, and a a wight spawn (our battle cleric), then we killed the wight, making the spawn a full wight, and a wight spawn, and 2 zombies, then we killed the wight and zombies as the third wight spawn (our Barbarian) rose.
Wights for a level 2 party... just say no.

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Ladies and gentlemen, I present the Drakainia. If you don't take real life SAN damage after reading "Invert Birth", I don't know what will phase you. Plus, the artwork in the Bestiary 4 is horrifying.
To be entirely honest, this is a pretty cool monster. I think I'm going to use it as the end boss for my campaign.