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The trail leads through the hilly terrain, and gets rough at many areas as if someone was utilizing explosives or druidic magic to prevent being followed. Eventually it leads to a very steep slope that would prove difficult for most to climb up.
Acrobatics to jump from rock to rock DC21
Climb to make the best effort possible in reaching the top DC21
Knowledge Nature to seek areas that may be easier to utilize DC21
Perception to look for a safer route DC21
Give me a creative solution and a skill check DC21
There appears to be a signs of a large reptilian creature that has passed through this area within the last hour.

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Climb: 10 + 16 = 26
Perception: 1d20 + 2 ⇒ (9) + 2 = 11
Captain Chlorophyll stretches their vines out and grasps with the tendrils into the rock face. They climb the cliff without problem, lowering a rope so others can follow.

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Acrobatics jump: 1d20 + 9 - 4 ⇒ (4) + 9 - 4 = 9
Perception: 1d20 + 6 ⇒ (8) + 6 = 14
Ralph tries to jump from rock to rock but...
"Curse this steep path!
I'm not built to face nature's wrath!
I'm just a simple lil city halfling,
Who sings in taverns for a bit 'o bling bling!"

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With the rope that Captain Clorophyll dropped to the rest of the party, the Climb DC is now 5 with the slope to brace behind it.
Botting Dr. Splash
Climb Check DC 5: 10 + 2 = 12
"This is not so bad."
Perception Check DC 15: 1d20 + 8 ⇒ (2) + 8 = 10
To continue onwards, I assume everyone can beat a DC 5 climb on take 10. You can still take perception checks.

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(Climb +9)
Perception DC15: 1d20 + 7 ⇒ (13) + 7 = 20
The Foreigner grasps the rope dropped by Captain Chlorophyll and scales the steep incline. Reaching the top, he looks around. He points at some lizard scat and other sign, "Large reptilian creature. Passed through this area within the last hour."

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Wertlos is grateful when Captain Chlorophyll drops the rope (take-10 beats 5...but not by much). "Thank you. I'm afraid I'm ill suited to this sort of thing."
Perception: 1d20 + 2 ⇒ (5) + 2 = 7

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Zahnlos jumps from rock to rock, pausing to sniff on the way up.
Acrobatics to jump: 1d20 + 14 ⇒ (11) + 14 = 25

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Captain Chlorophyll watches (obviously impressed) as Zahnlos leaps up the steep incline.
Pointing to the wolf, they say “Although you might have some difficulty, it looks like Zahnlos could have pulled you up!”

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"Hm. I suppose that's true. I have not tried riding on him, I don't know how he would react."

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“I don’t know either.” they admit. “I’ve heard that it takes training on the part of both the mount and the rider, but that may just be in bardic tales.”

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Another mischievous grin flashes across Ralph's face as he says to Wertlos:
"You and Zahnlos have a bond like no other!
Your connection is like brother to brother!
Nevermind those bardic tales from colleagues of mine...
I'm sure if you ride now, it'll all be just fine...."

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Botting Dr. Splash and Zephy
Take 10 Climb Checks.
Zephy Take 10 Climb: 10 + 2 = 12
Dr. Splash Take 10 Climb: 10 + 2 = 12
The trail continues to a large boulder. Searching around it reveals a tunnel that leads deeper inside the cave. It is a dark, stone cave that appears natural. The ceiling appears to be twice the height of the Foreigner or Dr. Splash.
Light or Darkvision will be needed to explore the caves.
Since I know the party has it I will just proceed.
The passage turns south, and the chamber spirals downward. A stone table lies at the bottom 10ft below, and bones litter the ground.
Proceed to next map, because it will be initiative time.

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Initiative Wertlos Kurz: 1d20 - 3 ⇒ (3) - 3 = 0
Initiative Mishka Krieger: 1d20 + 3 ⇒ (15) + 3 = 18
Initiative Captain Chlorophyll: 1d20 + 2 ⇒ (7) + 2 = 9
Initiative Rhymin' Ralph: 1d20 + 2 ⇒ (8) + 2 = 10
Initiative Zephirine Drouhin Tanglefruit: 1d20 + 2 ⇒ (15) + 2 = 17
Initiative Dr. Splash: 1d20 + 2 ⇒ (1) + 2 = 3
Initiative Tatzlewyrm: 1d20 + 2 ⇒ (2) + 2 = 4
Round 1
Initiative Order | Current Conditions
18. Foreigner | None
17. Zephirine | None
10. Rhymin' Ralph | None
9. Captain Clorophyll | None
4. Tatzlewyrm | None
3. Dr Splash | None
0. Wertlos | None
As you enter the cave, you see the tail end of some serpent like creature moving behind the rocks and letting out a low hiss as the light flares into the room.
The creature before you is a Tatzlwyrm. They are very aggressive territorial dragons that are particularily rare. They speak in Draconic.
Special Attacks: Poison Gasp, Pounce, Rake

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Pointing out the creature, Zephy readies her bow. "Stop there! We've come for information. Either discuss with us civil, or find yourself in pain!"
Intimidate?: 1d20 - 2 ⇒ (13) - 2 = 11

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Ralph will have the light cantrip going as needed.
Ralph activates archaeologist's luck, then tries to identify the serpent.
Arcana: 1d20 + 4 + 2 ⇒ (11) + 4 + 2 = 17
Arcana: 1d20 + 4 + 2 ⇒ (13) + 4 + 2 = 19
"The serpent is called a Tatzlwyrm!
They're territorial dragons that scare me till I squirm.
Can anyone speak draconic?
And convince it that our intentions here are totally plutonic?"
Ralph will then draw his crossbow and ready an attack should the serpent act in a hostile manner.
Piercing Damage: 1d6 + 2 ⇒ (5) + 2 = 7

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Captain Chlorophyll moves up and readies an attack for if the creature enters his reach.
Improved Unarmed Strike: 1d20 + 4 ⇒ (3) + 4 = 7
Blunt damage: 1d4 + 2 ⇒ (4) + 2 = 6

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As the party enters the dark cave, The Foreigner activates his wayfinder, illuminating the area around him like a torch.
Spying the creature lurking in the cave and hearing the bard identify it as a form of dragon called a tatzlwyrm, The Foreigner charges the beast, drawing his greatsword, foregoing any battlecry that might warn cave's guardian of its imminent death.
Greatsword, Power Attack, Charge; Damage: 1d20 + 8 ⇒ (18) + 8 = 262d6 + 7 ⇒ (4, 1) + 7 = 12
(Vigilante Talent: Shield of Blades - AC 14, T 9, FF 13 while using Power Attack)

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Round 1
Initiative Order | Current Conditions
18. Foreigner | None
17. Zephirine | None
10. Rhymin' Ralph | None
9. Captain Clorophyll | None
4. Tatzlwyrm | None Damaged: 12
3. Dr Splash | None
0. Wertlos | None
The Tatzlwyrm makes a vicious counter attack against the Foreigner, biting with a ferocious hatred for the intruder. It seeks to grab and latch on the Foreigner...
Bite Attack: 1d20 + 5 ⇒ (9) + 5 = 14
Bite Grab: 1d20 + 9 ⇒ (17) + 9 = 26
MISFORTUNE CHANCE!
Bite Attack Misfortune: 1d20 + 5 ⇒ (15) + 5 = 20
Bite Damage: 1d8 + 3 ⇒ (1) + 3 = 4
The Foreigner's deadly attack left him too open! In spite of fate twisting in favor of the party, the Tatzlwyrm still lands its attack!
The Foreigner takes 4 Bite Damage.
The Foreigner is grappled!

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Round 1&2
Initiative Order | Current Conditions | Damage
18. Foreigner | Grappled | Damaged: 4
17. Zephirine | None |
10. Rhymin' Ralph | None |
9. Captain Clorophyll | None |
4. Tatzlwyrm | Grappling | Damaged: 12+7
3. Dr Splash | None |
0. Wertlos | None |
Rhymin Ralph's readied action goes off! It hits the Tatzlwyrm with a satisfying blow. It is still alive and incredibly angry at The Foreigner.

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Just checking. With my readied having gone off, do I still have a turn this round?

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Caught in the tatzlwyrm's grip and with blood flowing from his wounds, The Foreigner curses under his breath, drops his greatsword, draws his cold iron dagger, and thunders, "Release me, wyrm, or I will slit your throat!"
[dice=Intimidate to Demoralize the Tatzlwyrm]d20+9[/dice]
(DC = 10 + the target's Hit Dice + the target's Wisdom modifier. If successful, the target is shaken for 1 round. This duration increases by 1 round for every 5 by which you beat the DC.)

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Captain Chlorophyll runs up and tries to kick the wyrm!
Kick: 1d20 + 4 ⇒ (8) + 4 = 12
Blunt damage: 1d4 + 2 ⇒ (3) + 2 = 5

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Ralph reloads his crossbow and fires it off at the dragon!
Archaeologist's luck, lingering performance: round 1
Crossbow vs AC: 1d20 + 4 + 2 ⇒ (19) + 4 + 2 = 25
Piercing Damage: 1d6 + 2 ⇒ (3) + 2 = 5

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"Zahnlos, រឿងដែលមានជនបរទេស! វាយប្រហារ!"
Wertlos shouts a command to Zahnlos, then steps forward a few feet as he draws a wand and activates it, suffusing the area with a ripple of positive feeling. 5ft step forward, draw and activate a wand of bless.

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Grrrrrrrrrr!
Zahnlos springs into action, bounding forward to attack the beast that has ahold of his comrade.
bite, bless: 1d20 + 2 + 1 ⇒ (17) + 2 + 1 = 20
damage: 1d6 + 1 ⇒ (2) + 1 = 3
trip, bless: 1d20 + 2 + 1 ⇒ (20) + 2 + 1 = 23

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"We could have been friends...but nooooo gotta do it the hard way." grumbles Zephirine as she lines up her shot.
Peering down the shaft of the arrow, she steadies her breath. Letting out a long slow breath, she releases the projectile, watching it soaring through the air, past her companions....and over the dragon thing. *clank* rings out softly as it deflects off the rocks beyond.
Using Precise Strike
Longbow, Precise Strike: 1d20 + 3 ⇒ (1) + 3 = 4
Longbow, Precise Strike: 1d20 + 3 ⇒ (3) + 3 = 6 <--Think I'll use this one to miss...
Damage?: 1d6 ⇒ 5
Waste of a precise strike! Oh well.

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Round 1&2
Initiative Order | Current Conditions | Damage
Foreigner (Grappled, -4)
Zephirine
Rhymin' Ralph
Captain Clorophyll
Tatzlwyrm (Intimidated,Grappling,-12,-7,-5,-3)
Dr Splash
Wertlos
The attacks from Rhymin' Ralph and Zahlnos are enough to make the tatzlwyrm finally crumple off of The Foreigner.

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Ralph reloads his crossbow and fires off another shot!
Archaeologist's luck, lingering performance: round 2
Crossbow vs AC: 1d20 + 4 + 2 ⇒ (12) + 4 + 2 = 18
Piercing Damage: 1d6 + 2 ⇒ (3) + 2 = 5

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The Tatzlwyrm lies unconscious, now bleeding out profusely. It is a shame that such a rare creature be unwilling to allow intruders into its cavern, but so is the life of a dragonkin.
In the pit down below the table has a mace laying upon it, and appears to have some compartments with a few random treasures. With magical detection there is the presence of a few items noticed, such as a wand and a scroll.
The mace, upon closer inspection, appears to be made of Cold Iron, and has a pentagram inscribed upon the head. A tarnished silver wire is loosely wrapped around the hilt, which reveals an inscription in Infernal along the handle.

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Moving towards the fallen creature, Zephy kneels beside it. Closely inspecting the wound a moment, she mumbles "The sap looks strange...maybe if I rub some mud on the wound..."
Alas, it continues to bleed. "Anyone able to help this thing? Sadly...my usual tricks don't seem to work on you fleshies..."
Heal Check to Stabilize: 1d20 + 4 ⇒ (1) + 4 = 5

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“They call it blood, and it is much thinner than sap.”
With a shrug, Captain Chlorophyll comes up and tries to treat the Draconic creature’s wounds. Washing the mud out, they then apply pressure to the wound and place some clean leaves over it as a bandage.
Untrained Heal: 1d20 + 2 ⇒ (17) + 2 = 19

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The Tatzlwyrm seems to have stopped bleeding, but it remains unconscious. Ralph's knowledge of the creature can discern that if you leave the lair it should not be seeking revenge, as they are primarily territory based creatures.

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Spellcraft: 1d20 + 7 ⇒ (13) + 7 = 20
"The wand casts pass without a trace.
We can now cover our tracks like an ace!
And I can read the scroll's magic.
It can create a fog cloud nice and thick!"

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Under the scroll and wand is also an old journal. It details the strategies and victories of someone by the name of Malgrin. It describes in detail his use of the foothills to lose pursuit, and how he utilized druids to cover his trails.
The journal has some interesting historical significance of Malgrin's tactical knowledge. It appears that this would be highly beneficial to the Pathfinder Society. It has good insight into the opposition during the Goblinblood Wars, detailing battles and war directions from Malgrin.
It also shows his concerns over new forces entering the field, and tactics on how to counter new arrivals.

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Kn: Local: 1d20 + 4 ⇒ (20) + 4 = 24
Paging through the journal, Captain Chlorophyll looks up for a moment to say "Wow! This information is better than any of the things we found in that library!"
Holding open the journal to a map with annotations, they add "Look at the tactical analysis they did! I bet Master of Swords Marcus Farabellus would want this."

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Dr. Splash looks over the journal as well.
Knowledge Local: 1d20 + 6 ⇒ (19) + 6 = 25
“Yes, it is a find! What a trove of scholarly information.” Then Splash turns to Captain Chlorophyll with a depth of seriousness. “Thank you for saving the Tatzlwyrm. I did not want to be responsible for a death of a dragon.”

The Amazing Urchin |

The Amazing Urchin turns to Foreigner and writes furiously. Did you hear THAT? The good doctor thinks they’re responsible for the death of a dragon when you guys did all the real work. Just blame it on the Hermean educational system. It’s not that great for developing critical thinking, if you know what I mean!

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Looking at the fallen creature, Captain Chlorophyll says “I hope it doesn’t cause any problems.”
Then looking at Dr. Splash, they ask “Is it really a dragon? I thought dragon’s had wings.”

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“It’s not as glorious as a real Dragon, but it is a draconic cousin... And as such, would hate to destroy it!”

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The mace carries the infernal writing, and it appears to be another part of the puzzle for this strange devil's name.
The party makes its way back to the capital to return to the Short Sorcerer Tavern, and find that Venture Captain Brackett has actually there for once. He is sitting at a now empty meeting room table, staring grimly into a piece of paper, and looks up to realize you all are in front of him.
"Ah, Pathfinders. It is good that you have returned in one piece. For a bit I feared the worst." He sets the paper down before him. "Unfortunately, it appears our job has a narrower time frame now."
He stands up. "It appears there is a surviving member of the Irrica family chasing the devil's name also, for her own purposes. Needless to say, we cannot allow it to fall into her hands." Then he lets out a smile. "The good news is we have another clue to this puzzle. A hellknight by the name of Dremlut Irrica was posted to an outpost in the Chitterwood."
He then hands you the letter he was reading.
Dremlut,
I pray this letter finds you safe. I know your duty to the Hellknights will put you in the path of danger, but yours is an honorable path, and I do not begrudge it. What concerns me is your faith in your own family. We are a jealous lot, and I fear my sister’s ambition does not rest easy alongside your rapid promotion. I worry that her peace will be bought with nothing less than your life. You do not believe me, but I know my sister better than you know your aunt. I pray you take care and to keep close the signet ring—should my sister try to command the Wrathful Angel against you, it will keep you and your companions safe. Remember to always wear it on your left hand; it was dearly crafted to shield you, my only child.
"According to the letter Dremlut has an enchanted ring that can possibly offer protection against the Irrica Family Devil. I believe you know what to do."
The venture captain then grabs a map and the letter and hands them both to you. "This map should help you to avoid all the known goblin ambush sites. If you encounter the Irrica with the devil, hopefully the ring will offer you some protection." The Venture Captain then loads up the last of his paperwork into a satchel. This meeting room now looks surprisingly bare compared to when you last came back.
"I will have to make my way back to Almas. I wish you the best of luck, Pathfinders."

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Several days of travel on trails that are not well tended, and several nights of restless sleep in the Chitterwood, the party eventually comes across a mostly collapsed encampment. Double checking with the map confirms it; this is the Hellknight Outpost, or at least it was.
The interior courtyard has been reclaimed by the local fauna and growth, and the Outpost shows all the signs of having been breached long ago. The only remaining structure is a single building in the southeastern section of the camp; its entryway boarded up with crude pieces of timber.
Proceed to the Last Map
On the remaining walls there are large spider webs in the shadows. Scattered amongst them are the bones of humanoid creatures, along with broken gear and equipment.

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Perception: 1d20 + 2 ⇒ (16) + 2 = 18
Pointing towards the shadows of one of the walls, Captain Chlorophyll says “We best be careful. It seems the spiders around here are big!”

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Perception: 1d20 + 8 ⇒ (12) + 8 = 20
“Agreed. Best be wary.” Dr. Splash clears some of the spider webs out of the way with their ranseur. “Are we ready to proceed?”

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In the Tatzlwyrm's Lair
Knowledge (local) DC15: 1d20 + 5 ⇒ (1) + 5 = 6
Hearing Dr. Splash describe the journal's contents, The Foreigner flips through its pages, fascinated with its potential. "The journal has some interesting historical significance of Malgrin's tactical knowledge. This would be highly beneficial to the Pathfinder Society. It has good insight into the opposition during the Goblinblood Wars, detailing battles and war directions from Malgrin. It also shows his concerns over new forces entering the field, and tactics on how to counter new arrivals."
He coughs at the mention of the Society's Master of Arms.
"Too many big words and not enough pictures for Master Farabellus, methinks. I'd like to show this to the esteemed military historian Yargos Gill at the Wounded Wisp. He's been know to work with the Society from time to time."
The Foreigner cleans his wounds and ties a linen bandage around his arm. "The wound will heal. The scars will remind me of the lesson I learned about charging a creature whose reach is greater than my own."
At the Chitterwood Hellknight Outpost
Perception DC14: 1d20 + 7 ⇒ (3) + 7 = 10
At the warning from Captain Chlorphyll and Dr. Splash, The Foreigner peers into the shadow, but still has difficulty spotting the creatures. Voice as soft and melodious as a death rattle, he whispers, "Do either of you recognize these spiders and know their strengths and weaknesses?"

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“Well, judging from the skeletons they will attack people —even people as big as Dr. Splash I would guess. Oh, and it is obvious they have webs.”
Looking around, they add “The problem is I see the webs and skeletons, but not the spiders.”

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Perception: 1d20 + 2 ⇒ (13) + 2 = 15
"Zahnlos, ተከላካይ." Wertlos stays close to his companion as he spots the webs hanging from the wall. "I do not like this place."

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As you creep ever forward through the web infested ruins towards the only standing building, the feeling of being watched is prevalent to everyone.
There is something making chittering noises inside the building.