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Improved cover is twice the bonus from regular cover, but does not prevent attack the way total cover does. The filament is not under any cover, though I should warn you that Ollo will take fall damage if it's broken.

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Ai focuses her mental energies sharply on the opening, trying her best to crush whatever will is inside and dull its senses, making it powerless against her next spell (if needed).
Casting Lullaby, targeting the entrance to the opening. DC 16 Will or -5 on Perception/-2 on Will vs. Sleep effects. Don't have eyes on the target,so there will be no Staring.

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Am I considered grappled? Or constricted? That would make a difference on what I do. Also, if I do fall, will you permit an acro check to mitigate some of the damage? Thirdly, Can I see anything of the creature above me?

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Neither, you're being pulled up by an adhesive filament. Acrobatics is fine. From your height you can see a brown claw and some antenna.

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"Aint gonna be no beasties snack today!" Ollo yells at the thing above him in rage. He pulls out his dagger, and slices at the filament dragging him upwards.
Damage: 1d4 + 2 ⇒ (3) + 2 = 5
Acro: 1d20 - 1 ⇒ (6) - 1 = 5
ooooo.... that's gonna leave a mark...

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Narika fires a magical bolt of energy and hits the filament which shudders but does not break. Ai casts a spell but there doesn't seem to be any noticeable effect. Ollo attempts to strike the filament but proves unsuccessful. Talon delays. ??? attempts to pull Ollo further up to it's cave but his flailing makes it difficult and he doesn't move any higher.
1d20 + 9 ⇒ (3) + 9 = 12
Round 1
Aarion
Talon
Round 2
Narika
Ollo
Ai
???
Aarion
Talon
For the sake of not wasting any actions, the next hit on the filament (AC14) will break it and drop Ollo causing 1d6 ⇒ 6 damage and knocking him prone.

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Aarion glances over his shoulder and acknowledges the dwarfs situation. Quickly the inquisitor moves up the rope in an attempt to beat the dangling dwarf to the top. Move or double move?
Climb (Taking -5 to move quickly): 1d20 - 5 + 5 ⇒ (4) - 5 + 5 = 4
Aarion's move is 20. Do to the shaded area, I'm not sure how much movement it will take to complete the climb. If Aarion doesn't require a double move, to finish the climb, he will cast shield of faith on himself. If it takes a double move to finish the climb, then disregard the spell.

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One movement should complete the climb. When you reach the tunnel you see a hole similar to the one Ollo is being pulled into.

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Eh, didn't think I would need an attack roll for cutting the filament since it was attached to me..
Attack: 1d20 + 3 ⇒ (7) + 3 = 10
Ollo continues to try and free himself, but ends up just swinging in circles. Suddenly getting an idea, and starts kicking his legs, trying to swing over to the rope Aarion just climbed up.
So I have no clue how the mechanics for that would work.. but my goal is to reach the rope and climb up of my own cognizance.

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At work now but I'll consider what kind of mechanics might work.
The filament itself is tough and you're dangling from it which would make an attack difficult to hit, imagine swinging your weapon at your shoulder or above your head.
Also I missed a bit of info, a hit is not a guaranteed break sorry about that guys. I'll keep an eye on this thread while I work to make sure I can let you know if/when it's broken.

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Ai frowns and unslings her crossbow, staring up at the hole and waiting...waiting...
Readied Crossbow: 1d20 + 5 ⇒ (14) + 5 = 19
Damage?: 1d8 ⇒ 8
Trigger is if the thing shows its ugly face.

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At half speed you make it almost up the wall but not quite to the landing, it will take one more move action to reach the top.
Ollo I did a little looking the the closest thing I could find to mechanics for swinging on a rope is from Skull and Shackles. We'll call it a DC 10 acrobatics check to make it to the rope along the wall, you will still be attached to the filament but if you make it I'll give you a +2 bonus to your CMD to avoid being pulled by it.
Still to go this round: Narika.

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Aarion makes it to the top of the wall and casts a protective spell on himself. Ollo attempts again to break free but does not succeed. Ai prepares to fire if the foe reveals itself. Talon starts to join Aarion at the top of the wall. Narika continues her assault on whatever it is pulling Ollo. ??? fails once against to lift Ollo any higher, in its frustration it moves directly over the hole, revealing it's soft brown underbelly, Ai fires and buries a bolt into the creature.
1d20 + 9 ⇒ (2) + 9 = 11
Round 2
Aarion
Talon
Round 3
Narika
Ollo
Ai
??? -15 Damage
??? is now only under regular cover (-4 to hit at range)

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Talon completes his climb, struggling to determine how best to help the hanging dwarf.
I'm hoping a single climb check (auto-succeed) gets Talon onto the ledge. That leaves him with a standard action, correct? Also, how much vertical distance between Talon and Ollo at that point?

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Not sure if you're looking at the map, but you can't complete your turn at the edge because that is where Aarion currently is. From the top of the ledge to Ollo is about 30ft down and he's hanging five feet to the left of the wall.

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Shield of Faith 1/20 rds.
AC 23 / T 16 / FF 18 / CMD 19
Aarion moves over to the available hole, and attempts to climb up.
Thats assuming the hole is large enough to fit through, and Aarion can get to it. If not, let me know and i'll change my action.
Climb: 1d20 + 5 ⇒ (14) + 5 = 19

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Aarion climbs into the hole (it's wide enough and low enough that a climb check isn't needed) and discovers two giant insects eagerly awaiting the meal their attempting to real in.

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Talon hustles after Aarion, clearing the lip of the climb and rushing to the secondary hole through which he sees Aarion disappear. (If he has enough movement to get up into the hole/cave where the spiders are), he draws his greatsword as Scorp prepares for any reprisals.
Climb to follow Aarion.
Climb: 1d20 + 4 ⇒ (2) + 4 = 6; sigh
.
Scorp readying an AA against whichever spider they see first.
Scorp, AA: 1d20 + 5 ⇒ (11) + 5 = 16; +2 to AC

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Ai takes another shot, shouting up to the advance party. "Hey, what's up there?!"
Readied Crossbow: 1d20 + 5 ⇒ (3) + 5 = 8
Damage?: 1d8 ⇒ 6

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Acro: 1d20 - 1 ⇒ (9) - 1 = 8
Ollo continues to try and catch the rope, only to be frustrated by dangling at the end of the line like a fish on a hook. Struggling, he tries to cut the filament again, taking a chunk out of it.
Attack: 1d20 + 3 ⇒ (13) + 3 = 16
Damage: 1d4 + 2 ⇒ (4) + 2 = 6

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Aarion and Talon discover the culprits attempting the reel Ollo in. Narika continues her missile launcher routine. Ai unfortunately does not make her mark but Ollo succeeds in making a dent in the filament though not as much as he expected. Purple attempts to pull Ollo up and once again fails. Purple skitters toward Aarion, hoping for a faster lunch but it's claws don't even come close to the Pathfinder.
1d20 + 9 ⇒ (4) + 9 = 13
1d20 + 5 ⇒ (1) + 5 = 6
Wow I have had some seriously poor rolls this combat, not a single roll over 4, which has drawn this out longer then intended.
Round 3
Aarion
Talon
Round 4
Narika
Ollo
Ai
Red - 19 Damage
Purple

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"PUT! HIM! DOWN!" Talon roars as he steps up to support Aarion, his massive blade crashing down onto the thing's carapace.
5' step into melee. Then attack. If this kills it, Talon's turn is finished. If it still lives, he'll use a swift action to get a Gore attack and use it on the same target.
Greatsword: 1d20 + 6 ⇒ (17) + 6 = 23
damage: 2d6 + 6 ⇒ (4, 4) + 6 = 14
.
Gore (if useful): 1d20 + 5 - 5 ⇒ (19) + 5 - 5 = 19
damage: 1d6 + 2 ⇒ (5) + 2 = 7
.
Scorp will focus on Red if it's still alive after Talon's attacks, or Blue of Red is down.
Scorp, AA: 1d20 + 6 ⇒ (2) + 6 = 8; nope

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Round 3
Shield of Faith 2/20 rds.
AC 23 / T 16 / FF 18 / CMD 19
Aarion moves slightly southeast, pulls his bow, and fires a shot at purple.
Not sure which Knowledge will ID the creatures, so Ill provided these two in hopes that one of them works.
Knowledge Nature: 1d20 + 5 ⇒ (1) + 5 = 6 (Attempting to I.D.)
Knowledge Dungeon: 1d20 + 5 ⇒ (5) + 5 = 10 (Attempting to I.D.)
(Free move action) Five foot step southeast, (Move action) Draw Composite bow from Aarions back, (Standard action) Take a shot at purple.
(Attack) MW Composite Longbow: 1d20 + 5 + 1 ⇒ (14) + 5 + 1 = 20
(Damage) MW Composite Longbow: 1d8 + 3 + 1 ⇒ (8) + 3 + 1 = 12

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Ai sends another bolt toward her target, this time aiming well and hitting something, but not very hard.
Crossbow: 1d20 + 5 ⇒ (20) + 5 = 25
Damage?: 1d8 ⇒ 1
Crit?: 1d20 + 5 ⇒ (18) + 5 = 23
Damage?: 1d8 ⇒ 3

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Acro: 1d20 - 1 ⇒ (15) - 1 = 14
Ollo finally manages to get a hold of the rope, and now that he has something to steady himself, he turns and tries to cur the filament again. "Bah.. ye'll be thinkin twice afor fishing fer dwarf again, I promise ye that, ya bugger!!!" he growls up at the cave.
Attack: 1d20 + 3 ⇒ (18) + 3 = 21
Damage: 1d4 + 2 ⇒ (2) + 2 = 4

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Talon relentlessly assaults the creature in front of him, causing it severe damage, but amazingly the creature still stands! Aarion, Ai, and Narika fire on the creature that has ensnared Ollo and see it fall limp. It's filament detaches and falls slack even as Ollo swings and grabs onto the rope along the wall, saving himself from fall damage! Red attempts to retaliate but the GM's poor rolling streak continues and Talon deftly dodges the giant claw.
1d20 + 5 ⇒ (2) + 5 = 7
Apologies, I had the damage attached to the wrong creature on the last wrap up.
Round 4
Aarion
Talon
Round 5
Narika
Ollo
Ai
Red - 21 Damage
Purple - Dead

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Talon sidesteps the creature's attack, but loses his balance. His response is way off-mark.
"Ollo!" he yells frantically when he sees the other creature fall, "you alright?!"
Attack it (no Battleshape this time)
Greatsword: 1d20 + 6 ⇒ (1) + 6 = 7
damage: 2d6 + 6 ⇒ (3, 5) + 6 = 14
.
Scorp focuses on Red
Scorp, AA: 1d20 + 6 ⇒ (11) + 6 = 17; +2 to AC against Red

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You were only barely able to see the enemy over the hole. The remaining one can only be seen by Talon and Aarion.

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Round 4
Shield of Faith 3/20 rds.
AC 23 / T 16 / FF 18 / CMD 19
Aarion takes a moment to observe the red creatures movement then makes moves slightly forward. Without delay the inquisitor draws his longbow back and fires on the red creature.
(Free move) Take a five foot adjustment south, (Move action) Study target on the red creature, (Standard action) Attack the red creature.
(Attack) MW Composite Longbow: 1d20 + 5 + 1 + 1 - 4 ⇒ (15) + 5 + 1 + 1 - 4 = 18 (Added a -4 for firing into melee combat.)
(Damage) MW Composite Longbow: 1d8 + 3 + 1 + 1 ⇒ (2) + 3 + 1 + 1 = 7

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Ollo calls back up the rope to where Tolon peers over the edge fearfully. "Aye! I'm good, lad. Be savin a few smacks fer me, though.. I've a conversation ta have with ta damn things!" Quickly, Ollo climbs up to the top of the rope.

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Ai lowers her crossbow, looking worriedly at the rope Ollo just finished climbing, and then pauses to glance at Narika. "I don't think there's much more we can do for them, do you?"
Out of viable actions short of two+ rounds climbing. It'll be over by then, right?

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At work now so I can't do a full update but combat is over. Aarion scored the final blow!

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As Ollo climbs through the hole and into the cave where the fight took place, he quickly surveys the scene. "Well, I'd 'ave rathered git a few licks in meself, but thanks fer tha help, boys. Damn things had me good.." he quickly searches the room before heading back down.
Perception: 1d20 + 3 ⇒ (7) + 3 = 10

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Talon is obviously relieved when Ollo appears. He goes about finishing off the creatures as he nods to the dwarf. ”You’re apparently a tough dwarf to kill.” He smiles, ”or is that redundant?”
Cleaning his blade, he goes about helping Ollo search the caves for anything useful.
Perception: 1d20 + 0 ⇒ (20) + 0 = 20
”Do we think there might be more of these things?” he wonders aloud, ”Because we might want to hurry on our way.”

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Once the threat of the insect looking creatures is over. Aarion climbs back down to where the rope is grappled, and stands guard while the rest of the group make the climb.
Once everyone has made it up safely, the inquisitor gathers his rope and grapple and then stows it in his pack.

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Talon discovers a number of humanoid bodies in the cave, among them are a number of useful items: a cloak of resistance +1, a potion of cure light wounds, a scroll of endure elements, a scroll of spider climb
The area does seem safe for now, and there's no reason not to continue as the party received no damage.
Following the tunnel at the top of the wall leads you to a narrow path leading up the mountain, hugging a sheer cliff face to one side, while dropping off to the other into what appears to be the remains of a rock slide. Several alcoves have been carved into the cliff face, each containing a small stone shrine—some little more than simple standing stones, others ornately carved lanterns or small houses. The path is well defined, promising easier progress, and is a welcome break from the rough terrain leading up to this point.
Map updated, because the mountain path is so narrow you must travel in single file, adjust the marching order if you need to. Everyone let me know when you're ready to move on.