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I say we keep pulling. We're halfway there already.

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Quick heal check to make sure we don't kill him.
heal: 1d20 + 1 ⇒ (18) + 1 = 19
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GM Harker |

Although slightly banged up, Kalkamedes appears mostly healthy when Melufiuos' gives him a quick check.
It takes almost another full minute, with the sleepwalking man resisting the entire time, but the group finally drags him around the bog. He does look a little worse for wear, however, as this time he receives a bleeding gash on the head.
The rough treatment doesn't appear to phase him, as Kalkamedes continues to pull on the rope in a direction away from the bog.
Attempt 1
Quiella's Primary Strength roll: 1d20 + 2 ⇒ (4) + 2 = 6
Cutter's Aid: 1d20 + 1 ⇒ (15) + 1 = 16
Halkale's Aid: 1d20 + 2 ⇒ (3) + 2 = 5
Nightrunner's Aid: 1d20 + 1 ⇒ (12) + 1 = 13
Melufiuos' Aid: 1d20 + 1 ⇒ (15) + 1 = 16
Ophelia's Aid: 1d20 + 2 ⇒ (3) + 2 = 5
T'kk'tck's Aid: 1d20 + 1 ⇒ (7) + 1 = 8
Kalkamedes' Strength roll: 1d20 + 2 ⇒ (13) + 2 = 15
Attempt 2
Quiella's Primary Strength roll: 1d20 + 2 ⇒ (5) + 2 = 7
Cutter's Aid: 1d20 + 1 ⇒ (13) + 1 = 14
Halkale's Aid: 1d20 + 2 ⇒ (20) + 2 = 22
Nightrunner's Aid: 1d20 + 1 ⇒ (11) + 1 = 12
Melufiuos' Aid: 1d20 + 1 ⇒ (13) + 1 = 14
Ophelia's Aid: 1d20 + 2 ⇒ (7) + 2 = 9
T'kk'tck's Aid: 1d20 + 1 ⇒ (11) + 1 = 12
Kalkamedes' Strength roll: 1d20 + 2 ⇒ (6) + 2 = 8
Attempt 3
Quiella's Primary Strength roll: 1d20 + 2 ⇒ (7) + 2 = 9
Cutter's Aid: 1d20 + 1 ⇒ (18) + 1 = 19
Halkale's Aid: 1d20 + 2 ⇒ (4) + 2 = 6
Nightrunner's Aid: 1d20 + 1 ⇒ (17) + 1 = 18
Melufiuos' Aid: 1d20 + 1 ⇒ (4) + 1 = 5
Ophelia's Aid: 1d20 + 2 ⇒ (10) + 2 = 12
T'kk'tck's Aid: 1d20 + 1 ⇒ (13) + 1 = 14
Kalkamedes' Strength roll: 1d20 + 2 ⇒ (7) + 2 = 9
Attempt 4
Quiella's Primary Strength roll: 1d20 + 2 ⇒ (1) + 2 = 3
Cutter's Aid: 1d20 + 1 ⇒ (2) + 1 = 3
Halkale's Aid: 1d20 + 2 ⇒ (2) + 2 = 4
Nightrunner's Aid: 1d20 + 1 ⇒ (8) + 1 = 9
Melufiuos' Aid: 1d20 + 1 ⇒ (18) + 1 = 19
Ophelia's Aid: 1d20 + 2 ⇒ (2) + 2 = 4
T'kk'tck's Aid: 1d20 + 1 ⇒ (13) + 1 = 14
Kalkamedes' Strength roll: 1d20 + 2 ⇒ (7) + 2 = 9
Attempt 5
Quiella's Primary Strength roll: 1d20 + 2 ⇒ (12) + 2 = 14
Cutter's Aid: 1d20 + 1 ⇒ (3) + 1 = 4
Halkale's Aid: 1d20 + 2 ⇒ (18) + 2 = 20
Nightrunner's Aid: 1d20 + 1 ⇒ (14) + 1 = 15
Melufiuos' Aid: 1d20 + 1 ⇒ (8) + 1 = 9
Ophelia's Aid: 1d20 + 2 ⇒ (18) + 2 = 20
T'kk'tck's Aid: 1d20 + 1 ⇒ (7) + 1 = 8
Kalkamedes' Strength roll: 1d20 + 2 ⇒ (9) + 2 = 11
3d2 ⇒ (2, 2, 1) = 5

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Quiella lets go of the rope and dings Kalkamedes with her wand before following him.
Wand, Cure Light Wounds: 1d8 + 1 ⇒ (3) + 1 = 4

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Quiella dings him a second time.
Wand, Cure Light Wounds: 1d8 + 1 ⇒ (8) + 1 = 9

GM Harker |

The second charge of healing seems to successfully cure all of Kalkamedes' wounds.
After the ordeal at the bog, Kalkamedes’s path winds westward into a steep mountain pass that climbs several hundred feet. The surface levels out only to terminate fifty feet ahead with a precipitous drop into a thirty-foot wide canyon. Unlike the two previous obstructions, there does not appear to be a way around without taking the sleepwalker far off course.

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Anybody have a grappling hook
I'm not really sure about how we should approach this.

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Mel hold rope until others tackle and tie him up
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Breathing heavily from the ordeal, Ophelia feels her heart sink when she sees the canyon. Putting aside her fatigue, she attempts to greab Kalkamedes before he can head off the cliff.
Grapple: 1d20 + 3 ⇒ (5) + 3 = 8
And nearly trips over.

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Mel cringes and holds tighter to the rope.
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"We may have to employ more drastic measures to protect him!" Cutter warns, leaping from the saddle as a flying tackle at Kalkamedes.
Grapple: 1d20 + 2 ⇒ (13) + 2 = 15

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Seeing her companions let go of the rope, Quiella tries to grab Kalkamedes legs to make Cutter's attempt easier.
Aid Another, Grapple: 1d20 + 2 ⇒ (9) + 2 = 11
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GM Harker |

Although both Ophelia and T'kk'tck have difficulties restraining Kalkamedes, Cutter and Quiella work together despite their smaller sizes to grapple the man.
Kalkamedes reacts violently to be restrained once more, socking Cutter extremely hard between the plates of his armor. 5 bludgeoning damage to Cutter.
Punch-grappled: 1d20 + 4 ⇒ (16) + 4 = 20
Damage: 1d3 + 2 ⇒ (3) + 2 = 5

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Cutter maintain his grip on the man, and tries to pin him! "Pile on my pack!" the halfing shouts! "Tie him up with the rope already attached!"
Grapple (maintain): 1d20 + 2 + 5 ⇒ (11) + 2 + 5 = 18

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Mel looks for something to tie his end of the rope to. Tree, rock, stump, sleeping dragon
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GM Harker |

With the help of Halkale and T'kk'tck, Cutter manages to pin Kalkamedes to the ground. The sleepwalker resists and almost wiggles out, but the halfling is able to keep him restrained.
Melufiuos sees some large rocks nearby, but no sleeping dragons.
If you have rope and haven't acted yet in this round, you can tie Kalkamedes up now. Otherwise, Cutter will have to make another check to keep him pinned. Once tied up, the difficulty for him to break out will be the CMB of the person tying him up + 20. If it's sufficiently high, he won't be able to untie himself even on a natural 20.
Escape Grapple: 1d20 + 6 ⇒ (8) + 6 = 14

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I used my action to look for rocks? If not, I want to tie the rope to it. If so, I'll wait until next turn. I'm sure everyone else has things under control.
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Oh, didn't realize I needed to post a new action. Still helping Cutter keep Kalkamedes from climbing over the edge.

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Ophelia draws her own rope from her pack and attempts to tie up the unconscious scholar.

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"Let's toss him over Nightrunner's back and get him to safety. We can lash him to the saddle." Cutter suggests.

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Quiella looks at the ravine. "How do we cross this thing? Cutter and Halkale, can you find a way around?"
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Feeling Halkale has it well in hand, Cutter offers his opinion on the terrain.
Survival: 1d20 + 7 ⇒ (7) + 7 = 14

GM Harker |

Unfortunately, both Halkale and Cutter can see that there does not appear to be an easier way to deal with the crevice than to try to cross it. Attempting to go around will mostly like take Kalkamedes far off course from his destination since the group currently finds itself in a mountain pass.
The sleepwalker struggles against his bonds, but is unable to escape.
1d20 + 6 ⇒ (1) + 6 = 7

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Life is playing hardball right now. I'll have a post either late tonight or early in the morning. Right now on a brief glance over I'm unsure what T'kk'tck should do. Can we see the bottom of the ravine. Does it look like we could lower ourselves and him to the bottom and continue from there?

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Yeah, I'm thinking we just need to lower him down there. The only confusing part is who goes down first to protect him (I'm sure there are nasties just waiting for us) and who will be left up here alone to come down last?
I have climb 3
One of the ropes is partially tied around the dude. It is 70' down. How many other ropes do y'all have?

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I've used my rope to tie him up. Also, I vote the cleric doesn't go down first, because if there are nasties, I'll be the one who has to heal you all.

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Cutter is a terrible Pathfinder. He only has a crowbar, no rope. :D

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Halkale has 50 foot of silk rope, which is hopefully not what we tied him up with, since it's stronger and more expensive

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the ravine is only 30' across. I thought we would throw a grappling hook over and cross directly.
-Posted with Wayfinder

GM Harker |

Doing a quick check of the group's character sheets, it doesn't look like anyone has a grappling hook. If you want to use rope to climb up and down the full 70 ft., you'll need two ropes. The climb will be easier if the ropes are knotted.
I believe currently Kalkamedes is restrained by Ophelia's rope, while Halkale's rope has been acting as his leash, which is also still tied to Kalkamedes as well as a nearby rock.

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No grappling hooks? I/we fail as Pathfinders. Up and down it shall be, except... how are we getting back up the other side without... a grappling hook?
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Hmm. Gnomes are small. "Ant Haul" makes them light. Throw in "Throw anything" and add a vial of "make me stronger". Nothing would go wrong, I'm sure of it. What's the worst that could happen? And I've got 50' of rope you could carry with you.

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Perhaps you should make this suggestion IC. Partly just 'cause, partly because I need you to state exactly what you have in mind a little more clearly.

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T'kk'tck picks himself up and holds up a claw.
"A thought occurres! Our small friends here aren't that heavy without all the stuff they are carrying."
He gestures at the halfling and the gnome.
"I have a few bottles here,-" while talking he pats his robes searching for the items in question. "Aha. Yes. This one enables me to carry more than I can normally. And this one, enhances, yes that's the word. Enhances my strength. If I took both of them and then grabbed one of you while you held onto a rope I could throw you across the way over there and you could pull us all across."
The longer he talks the more excited he gets about the plan and the mania starts to edge into his voice.
"This is a great plan. We can totally do it. You! Start taking off the heavy stuff yes? Tell me when you are ready and I launch you."
As he looks for an adequate spot he mumbles in another language to himself.
"It should work. Of course it would work. I hope... And if it doesn't I'm sure everything will be fine."