Octopi are supposed to be pretty smart, but usually when they attack people in the water in fantasy or pirate media they just latch on and try to drag them down or whatever. What else could they be doing? Let's typecast them a bit like the goblins of the sea: a large group of small, semi-intelligent feral creatures attacking whoever they see, relying on cleverness instead of brute strength.
Roll d10 if it's a terrestrial attack (or on the deck of a ship)
Roll d10+10 if it's an attack in a flooded cave or sewer with knee-high water
Roll d20 for an attack where the players aren't swimming about
Roll d20+20 for an attack in the open ocean
Roll d10+30 for a magical octopi attack.
Roll d10+40 for a giant octopus attack.
Roll d50 for a totally random Octopi attack
[1] Octopus jumps on your head, classic facehugger tech.
[2] Octopi swing on vines, ropes, or tentacles of an even bigger octopus; curl up around the end of the cord and use their bodies like little wrecking balls.
[3] Two Octopi wrap their tentacles together and pull, making a tight tentacle rope right under your feet so you fall face first.
[4] Octopus curls up around a rock or cannonball, another octopus grabs its tentacles as a bit of rope and swings it around its head. Then, the curled octopus lets go, like a living sling.
[5] Octopus grabs a bunch of knives, forks, shrapnel; spins in a circle madly as a deadly beyblade.
[6] Ink sprayed on the floor acts as oil slick, leading right into a pit or the side of the ship.
[7] Giant spiders crawl on the ground to reach you, two legs up to strike. Actually Octopi painting themselves black or using camouflage skin, intimidation tactic.
[8] Octopi hang on to the heads of stampeding cows, pigs, horses, etc. Covering their eyes with their tentacles as blinders, trying to guide them to run you over.
[9] Octopi hang from the rigging, jungle vines, or stalactites and climb around like monkeys, holding small sharp knives in their tentacles and slicing downwards with acrobatic swings.
[10] Octopi holding onto old ropes and chains swing around your legs in circles to entangle you, give you the Star Wars AT-AT special.
[11] Carefully floating on the surface, spread out and mimicking pond scum or water lilies; the octopi wait to get close and then leap on to you all at once.
[12] Octopi release a cloud of acid around you in a circle, then throw stones over the water's surface to pelt you to death. You can move out of the area and attack them directly, but you take damage.
[13] Octopi lay out flat along the bottom of the water, face-up, arms stretched, ready to wrap around and bite any foot or hand who touches them; living beartraps.
[14] Octopi hold open a small sluice gate or drain-latch in the area to create suction, trying to get you washed away or control the water level for a better encounter.
[15] Octopi wrap around legs and arms, holding on to each other like a chain to pull you down under the water and drown you.
[16] Octopi carefully hold together to stretch over a pit or recession in the water; wait for you to step on them thinking it's the floor until they give way and now you're swimming neck deep while they attack.
[17] Crocodiles bump into your feet, look like something is growing around their face. Octopi keep their mouths shut, before releasing right as you get close. They've been starving them to make them extra aggressive as they swim away to leave you to fight the bigger beasts.
[18] Octopi keep along the side of the passage tightly under the water, holding long spears or axes leaned upright. When you pass by, they drop them all at once, letting gravity do the work.
[19] Hide in the water underneath stones, within rusted suits of armor, attack with long skewers and splints of wood like little pillbox bunkers. Only come out to dart to a new hiding place in hit & run guerilla warfare.
[20] Octopi crawl together and form a human sized megazord! Picks up weapons and fights as a Fighting-Man with high skill and speed; its "limbs" detaching and bending around at angles a human never could to make up for its lack of armor and bones.
[21] Octopus holds eight flying fish in its tentacles, strategically positions beneath swimming person, releases them like upwards swimming missiles.
[22] Seal swims up with something in its mouth. Surprise! Octopus jumps out.
[23] Octopi ride manta-rays, bits of seaweed as reigns, jousting at you with long stingers. You could also do this one in a sewer or waist-high depth of water, just assume it's a poopray or swampray or fantasy cliff racer or whatever.
[24] Octopi wrap around a solid bit of stone or sinking object and the other end around your foot to drown you, or drag you down with it.
[25] One Octopus wraps around your weapon increasing its drag and making it slow and unwieldy, while the others try to bite and grapple you with normal attacks. Above water this doesn't work very well since the octopus would just get splattered, but underwater it can increase drag by a lot.
[26] Octopi hold small crustaceans and fish in their tentacles, wriggling but alive. They break them apart and rip them up turning the water red; attract frenzied sharks.
[27] Two Octopodes grab the ends of a long sword blade or rusted saw fallen in the water, attempted decapitation.
[28] Using all eight of its arms, Octopus holds on to the end of an eel which it uses like a whip weapon.
[29] Bunch of Octopi with their tentacles all tied together in knots; like a rat king but less effective.
[30] Octopus carefully holds sea urchins with the tips of its tentacles; tries to swim into your trunks or gaps of armor and pull them in tightly.
[31] Octopi spit out strangely shiny ink in a long path towards something burning or an underground vent; special flammable ink creates a trail leading right to you underwater.
[32] Hypnotic Octopus eyes surround you from each direction; trying to look away and they just keep staring as they surround you. Why can't you just close your eyes? Well uhh...
[33] Octopi swim together and link tentacles, forming a giant magical "Rune of Boil Water".
[34] While you're distracted, a small poisonous octopus squeezes off a cork on one of your potions, squeezes inside, camouflages itself as the liquid, and waits to strike.
[35] Three octopi curl around a magic wizard staff that fell overboard. Difficult to coordinate, but when they do, fires out concussive blasts.
[36] Ties a bit of warpstone/radioactive rock/necrotic infused artifact to the end of a long cord, swims very close to you and past to try and hit you with it; leaves a trail of dangerous water just behind in its wake.
[37] Undead skeletons act like mech suits; octopi hide in the ribcages and poke out with long sticks or fish bones. If you break the skeleton apart with a strong hit, they'll swim and scatter for cover.
[38] Octopus stretches out all its legs and rotates in place, making a spherical zone of air that it launches as a bubble that traps you inside it. Not actually dangerous at all if you can breathe air, but prevents you from swimming away until you pop it and get back in the water.
[39] Octopi mimic and shape themselves as other aquatic animals, changing their skin coloration to match. They're so good at it that they actually appear as those creatures; must roll to disbelieve or panic at fighting sea monsters that aren't even there.
[40] Octopi release swarm of tiny eggs which fly at you and attack, touching you to explode and deal minor magical damage. Wouldn't be a big deal but there are so many they can give you death by a thousand cuts.
[41] Giant sheet metal or slab or rock is held by this kraken in all its tentacles, hovers above you casting a shadow. Releases it to let it drop and fall: pinning you beneath its weight and to the depths you go.
[42] Giant Octopus uses it water jet air cannon valve thing right at you; water jet slipstream that can slam you back into walls and discombobulate you or makes you drop your weapon so it can grab and squeeze you to death. Maybe it shoots ink instead?
[43] Octopus grabs the mast of a sunken ship, giant whale bone, or something similar and stabs it as a giant spear. Each tentacles helps push and pull to make it fast and accurate.
[44] Giant Octopi pushes a parasitic egg into you with the tip of its tentacle whip attack. It grows inside your flesh by draining your hit points and after enough combat rounds it hatches and creates a smaller regular octopus that immediately attacks you. You can attack the egg early to kill it before it hatches, but distracts you from fighting the big one.
[45] Stretches out all its tentacles and starts to spin around really fast. Creates a vortex that sucks you in or blows you away, spinning everything smaller then the kraken with its powerful pull.
[46] Giant Kraken grabs two large shields or metal objects and bangs them together hard, creates a shockwave that deafens and stuns nearby targets, maybe grab eight objects for a maximum of four powerful concussive claps every round.
[47] Retains the camoflague abilities of a normal Octopus even at giant size. Big enough to have entire fake creatures, escapes out of the underwater cave, loot chests, or even your own allies projected onto its skin; all illusions to draw you in or confuse you as to where the location of its body actually is.
[48] Spews out so much ink that the nearby water becomes more ink then water; swimming through it becomes difficult, snuffs light sources, water-breathers can't breath in it any more, and so on. Maybe after a few rounds it congeals, becoming like a thick rubbery prison for anyone still within the black cloud.
[49] Wraps your arms in one tentacle, legs in another, then tries to pull you apart. I know this isn't very creative or weird like the others on this list but how often do you see giant squids actually try stuff like this instead of just slapping people with their tentacles and constricting them??? It's great!
[50] Wraps all its tentacles around you, jets up, and bodyslams your ass onto the nearest solid object out of water like the shore or the deck of a ship using its big squishy cephalopod weight.
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