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Jarlaxle casts Detect Magic.
No ranks in Spellcraft, though.
Perception (Vs. the potion): 1d20 + 7 ⇒ (14) + 7 = 21.
I still say we clad him in his equipment, wind him up, and let him go, with at least a couple of us (preferably Perceptive/Survivalist types) scouting, say, 100' ahead of him, to try and scope-out any dangers.

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I still say we clad him in his equipment, wind him up, and let him go, with at least a couple of us (preferably Perceptive/Survivalist types) scouting, say, 100' ahead of him, to try and scope-out any dangers.
Agreed. And a rope might be nice too--fer cliffs and rocs and such.

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Jarlaxle notices with detect magic, that the blue liquid, as well as whatever is inside the gourd, and flask radiate, plus the sword as magic. With a taste of the blue water, the elf realizes that it is an elixir of swimming. After a few minutes of talking, everyone decides to dress up Kalkamedes into his adventuring gear before cutting him loose, letting the man walk to where he wants. Sheila Heidmarch looks at the party and asks, "While those may have been stashed away, shouldn't you take those items along, as they may help out somehow?"

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We might want to hold on to some of that stuff. It wouldn't do for the only healing potion to be in the possession of someone who might not recognize its worth, for instance.

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Ray, scouring over all the items, realizes what the items or other contents in the items are. The newly identified items are bracers of armor +1, a mud spattered cloak of resistance +1, the gourd has enough cure light wounds for one drink, and the sharp mithral flask contains enough hide from undead for one drink. The sword, he also notices, even though broken, is a +1 mithral longsword.

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"Some good stuff here."
Ray will pocket the mithral flask. "These bracers and cloak would certainly be useful to me, but I expect they would be more useful to some of you who like to get into the fight, if ever there be one. And this potion I can hold onto for now, in case we ever need to revive Jarlaxle. Of course, I'm not expecting much of a fight tonight, unless we run into a badger nest or something..."

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Creat's good on packing silver, but if the cloak looks stylish he'll nab that. Once Kalkamedes is equipped and tied to about 50 ft. of rope let's go.

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Sorry about the delay, and off we go! So, who's holding the rope?
After equipping Kalkamedes as best they could, and taking his items in case they're needed, the group ties the man on a leash, and cuts his bindings. Sitting up with a big snore, the sleeping man starts to make his way out the cabin and into the woods. The nearly cloudless night shines bright with moonlight, enough so that torches aren't needed to see the path.
Is anyone keeping a close eye on the man, and able to help him if he falls?

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I am going to go with: Half-Orc on the other end of the rope; Jarlaxle and Creat scouting ahead; Ray (our squishy caster) keeping a close eye on Kalkamedes for any problems, alerting the others as necessary?
Let's get this show on the road :-)

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Sometimes, only a pebble is needed to create a wave, haha. Also, did anyone take the sword, or did you all strap it to Kalkamedes?
The group heads out into the clear night, bats and birds chirping alongside the croaks of frogs and the occasional snore from the mighty Kalkamedes. For a while, the escort mission seems to be going along smoothly, even with the man falling every so often, Umaga catches the sleepwalker without issue.
About an hour an a half pass from their leaving of the cabin when Jarlaxle and Creat spot a large copse of thorny shrubbery, measuring about forty feet wide at a quick glance.
Yay, beat the first hurdle as you mentioned that an eye would be kept on the man. Now, how are we going to guide the man through this obstacle?

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Leave it with him. It is magical, but it is also broken, so I don't think any of us would prefer to wield it.
Knowledge(Nature): 1d20 + 2 ⇒ (6) + 2 = 8.
Jarlaxle eyes the copse of thorny brambles warily, before rushing back to Umaga and Kalkamedes.
"Okay, we need to drag him about 40' off to one side; I would rather he didn't get cut to ribbons as a result of wandering through a briar patch!"
Strength(Assist) to drag Kalkamedes: 1d20 + 4 ⇒ (6) + 4 = 10.

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.... did anyone take the sword, or did you all strap it to Kalkamedes?
I would take it, but I have a silver weapon.
About an hour an a half pass from their leaving of the cabin when Jarlaxle and Creat spot a large copse of thorny shrubbery, measuring about forty feet wide at a quick glance.
Alas it seems we should have brought a herring.
The best I can manage on the unskilled roll is 10. So....
"Joy. Which one of you guys is the cleric?"
How big's the patch. Could we navigate around it quickly or does it reach the horizon.

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It looks to be about 40' wide from where you're standing, but goes past your vision in the low light condition. I'd like to say more, but it's an easy obstacle to pass, if Kalkamedes doesn't "rush" into the briar patch.

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Agreed.
"Right then. I guess I'll scout for an edge."
Stealth (sneaking ahead): 1d20 + 7 ⇒ (10) + 7 = 17
Perception (looking around): 1d20 + 3 ⇒ (6) + 3 = 9

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Well, Umaga is about to find something out.
As Umaga attempts to grab the man, Kalkamees swings his arm at the half orc! Ducking under the wild swing, Umaga grapples the man and starts to walk with the human around the shrubbery.
attack: 1d20 + 6 ⇒ (5) + 6 = 11

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Well, Umaga is about to find something out.
As Umaga attempts to grab the man, Kalkamees swings his arm at the half orc! Ducking under the wild swing, Umaga grapples the man and starts to walk with the human around the shrubbery.
If only we had a herring to clear the path with.

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Kalkamedes Punch!: 1d20 + 6 - 2 ⇒ (9) + 6 - 2 = 13
With assistance from Jarlaxle, the group manages to get past the razor bramble and Kalkamedes' swings towards Umaga. After being set down, Kalkamedes keeps on heading along his path for about another hour, and stops for a moment. After the slight pause, he turns left and begins walking once more. The air becoming more humid, and the sounds of flying insects growing, the group notices that the ground starts to get softer and softer before Creat and Jarlaxle step solidly into ankle deep mud.
Looking ahead, the elf notices that their party has come upon a bog, and in this light loogs to be about 40 feet to the other side, and stretches about 100 feet across.

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"Come on everyone! Let's drag him round - I doubt he wants to drown in mud..."
He, once again, attempts to drag the man around the obstacle.
Grapple: 1d20 + 5 ⇒ (15) + 5 = 20.
One question: If the man is sleepwalking, and therefore cannot see what is happening around him, how can he take AoOs? We have total concealment...?

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It's actually written that he fights pretty much only those who grapple him or blocks him from moving, and leaves everything else alone. Other than that, there is a 50% chance to hit, which I forgot to put in, so that's my bad! A good suggestion, at least from the other table being run, is more to guide/drag him rather than grapple. He'll fight back somewhat, but it's better than getting hit by a sleepwalking man, haha.
Percentile: High Good: 1d100 ⇒ 80
Punch: 1d20 + 6 ⇒ (15) + 6 = 21
Damage: 1d3 + 2 ⇒ (1) + 2 = 3
Jarlaxle, attempting to grab Kalkamedes, gets punched in the arm before grappling the sleepwalking man, keeping him from moving further into the bog.
It's easy to grapple him, he does have a good to hit though....

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Fair enough. I would have thought he would resist *once* grappled, not in the process of being grappled, but if that is the way the module is written, I won't argue ;-)
"Okay people, let's keep moving!"
Jarlaxle continues to drag the man around the bog.
CMB: 1d20 + 5 + 5 ⇒ (15) + 5 + 5 = 25.

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Can I use the rope tied to me as the "trailer", to drag him or something like that away from the bog?
That was part of the idea behind the rope.

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Sorry about the delay!
With Umaga's help, Jarlaxle manages to guide the sleepwalking man around the big towards the other side to safety, as they use the rope similarly to a leash. The trail goes on and starts to slope up. After about an hour, Creat and Ray who are scouting come to a clearing. Fifty feet away from them, looks to be a drop from the path that they were traveling on. When looked down, it appears that the cliff is about 100 feet high.
The scouting party just gave extra time to decide as what to do to the sleepwalking Kalkamedes, who currently has 80 feet before the drop.

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assuming it isn't possible to drag him around the ravine, I guess we need to lower him down, then haul him up the other side...?
Jarlaxle throws another loop of rope around Kalkamedes, and then tosses the end to Creat.
"Quick! Get down the ravine, and then up the other side! We'll lower him down, and then we can haul him up the other side!"