The climb is straightforward; no rolls are needed.
Ben peers through the open window. Old, empty birdhouses are nailed to the walls of the cramped room within, and a dozen birdcages hang from the ceiling. The cages are filled with tiny clockwork sparrows. As the birds’ gears turn, the air thrums with rhythmic ticking. Paper and quills are heaped on a small writing desk under the cages. Carved into the wall above Ben's window is the word “Hither,” and above the second window next to it is the word “Yon.” There are no other occupants. A closed interior door leads northeast.
=========
Meanwhile: Titaani: Make a contesting DC12 Athletics or Acrobatics check to resist the grapple.
Just about to open the “Yon” window, Ben hear’s Titaani’s voice and looks that direction. Seeing only her tiny friend, he tries to make the connection quickly in his head…
Intelligence: 6
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Gerrard Feldren - Human Noble in Ghosts of Saltmarsh
Kerric Brightblade - Elven Warrior in "Apocalypse"
Pud creeps into the room behind Ben. His ears perk up when he sees the clockwork bird, which reminds him of his own clockwork companion. He knows the mischief that his own bird can get into so he sends Rizzo up to distract the bird.
Rizzo flutters up to buzzes around the target attempting to block their vision.
Pud, not being incredibly familiar with Tiny, is perplexed at what just happened with Tiny.
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Pronouns: he/him/his
Pud - lvl 7 Human Artificer - Alchemist (The Wild Beyond the Witchlight).
Quinn - lvl 4 Human Ranger - Hunter (Phandelver and Below: The Shattered Obelisk)
The mechanical birds whir and tick as they move about in their cages.
Ben opens the door to a bedroom. Almost everything about this bedroom is orderly, from the bed with the patchwork quilt to the ornamental pigs arranged in a neat row on the dresser. Such tidiness is at odds, however, with the decaying dollhouse sitting on the bedside table. This three-foot-tall edifice has seen better days and is now besmirched by peeling paint, mold, and rot. Behind the dollhouse, by a window, moths flutter inside a large bell jar. Another pair of doors leads out. Next to that door is a wooden rocking cradle with a neatly folded blanket in it. Pud has never been in here, but he knows exactly where this is: Granny's bedroom.
Meanwhile, Matilda catches a glance of Titaani being lifted into the sky by Cradefall, maybe fifty feet away on the other side of the log. She is now some 30 feet above the ground. (Titaani may act - to try to break the grapple or try something else. Everyone else may act, too!)
Pud waves his hands frantically trying to shush the party. He points at the decrepit dollhouse and does his best with hand gestures and ugly faces to indicate that Granny might be in there sleeping.
DM: how large is this room? Would there be enough room to cast flaming sphere and use a bonus action to ram it into the dollhouse?
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Pronouns: he/him/his
Pud - lvl 7 Human Artificer - Alchemist (The Wild Beyond the Witchlight).
Quinn - lvl 4 Human Ranger - Hunter (Phandelver and Below: The Shattered Obelisk)
Realization dawning on his face, Ben mouths, “To the oven in the kitchen?” and spreads his arms wide, indicating he would be willing to carry the dollhouse.
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Gerrard Feldren - Human Noble in Ghosts of Saltmarsh
Kerric Brightblade - Elven Warrior in "Apocalypse"
This post has potentially manipulated dice roll results.
"What are you doing?" Titaani yells, panicked, at Cradlefall. "Putme down at once! Or...or else...I'll...I'll curse you! And make your life miserable!"
Intimidation: 23
Rollback Post to RevisionRollBack
Pronouns: She/her/her's
Currently playing as Titaani Leelathae in The Wild beyond the Witchlight
Pud nods in agreement with Ben. He points at Horatio and Ben motions towards the kitchen. He then pokes himself in the chest and points to the window. He imitates an archer firing a bow and arrow and then flaps his arms like a dragon taking flight.
Pud creeps over to the window. He draws his magical multi tool spell focus and with a flourish and uttering of some magical incantation a magical arrow dripping with acid arcs across the sky towards Cradlefall.
Action: Cast spell acid arrow at Cradlefall. 18 to hit for 13 acid damage.
Rollback Post to RevisionRollBack
Pronouns: he/him/his
Pud - lvl 7 Human Artificer - Alchemist (The Wild Beyond the Witchlight).
Quinn - lvl 4 Human Ranger - Hunter (Phandelver and Below: The Shattered Obelisk)
This post has potentially manipulated dice roll results.
Climbing fully into the bedroom, Matilda grabs the glass jar of moths off the southern windowsill and throws it out the "Yon" window, hoping for a lucky strike on the fleeing dragon. (Alas, it is a very long shot. Disadvantaged attack roll: 10)
"I'll put you down soon enough," reassures Cradlefall, icily.
Pud steps in behind Matilda and releases a shimmering green arrow from his bowless hands. It hits its target. Cradefall shrieks in rage and pain but continues to rise into the air with Titaani.
(The bedroom is large - it is a circle 40 feet in diameter. Plenty of room for a 5' ball of fire.)
Horatio holds the bottom of the line to keep it steady, offering help to everybody else before going up himself.
( Athletics to climb after everyone else does - 23 )
The climb is straightforward; no rolls are needed.
Ben peers through the open window. Old, empty birdhouses are nailed to the walls of the cramped room within, and a dozen birdcages hang from the ceiling. The cages are filled with tiny clockwork sparrows. As the birds’ gears turn, the air thrums with rhythmic ticking. Paper and quills are heaped on a small writing desk under the cages. Carved into the wall above Ben's window is the word “Hither,” and above the second window next to it is the word “Yon.” There are no other occupants. A closed interior door leads northeast.
=========

Meanwhile: Titaani: Make a contesting DC12 Athletics or Acrobatics check to resist the grapple.
The party hears a gasp of delight which turns into a shriek of surprise come from Tiny's mouth. The voice is recognisable as Titaani's.
Acrobatics: 13
Pronouns: She/her/her's
Currently playing as Titaani Leelathae in The Wild beyond the Witchlight
Ben:
Just about to open the “Yon” window, Ben hear’s Titaani’s voice and looks that direction. Seeing only her tiny friend, he tries to make the connection quickly in his head…
Intelligence: 6
Gerrard Feldren - Human Noble in Ghosts of Saltmarsh
Kerric Brightblade - Elven Warrior in "Apocalypse"
Pud creeps into the room behind Ben. His ears perk up when he sees the clockwork bird, which reminds him of his own clockwork companion. He knows the mischief that his own bird can get into so he sends Rizzo up to distract the bird.
Rizzo flutters up to buzzes around the target attempting to block their vision.
Pud, not being incredibly familiar with Tiny, is perplexed at what just happened with Tiny.
Pronouns: he/him/his
Pud - lvl 7 Human Artificer - Alchemist (The Wild Beyond the Witchlight).
Quinn - lvl 4 Human Ranger - Hunter (Phandelver and Below: The Shattered Obelisk)
Matilda climbed up with a confused expression, " Why are we doing this? This seems....like we're all gonna get captured....again..."
Her head whipped around at Tinys gasp, " Titaani? Where are you?" You need help?"
Horatio looks to Matilda, "You're right, this would be a lot better if we knew exactly where to go. Where was Titaani supposed to go in your plan?"
" The kitchen. Thats all she said that I remember."
Ben:
Moving into the room, Ben goes and opens the door, listening for Titaani’s voice.
Perception: 16
Gerrard Feldren - Human Noble in Ghosts of Saltmarsh
Kerric Brightblade - Elven Warrior in "Apocalypse"
The mechanical birds whir and tick as they move about in their cages.
Ben opens the door to a bedroom. Almost everything about this bedroom is orderly, from the bed with the patchwork quilt to the ornamental pigs arranged in a neat row on the dresser. Such tidiness is at odds, however, with the decaying dollhouse sitting on the bedside table. This three-foot-tall edifice has seen better days and is now besmirched by peeling paint, mold, and rot. Behind the dollhouse, by a window, moths flutter inside a large bell jar. Another pair of doors leads out. Next to that door is a wooden rocking cradle with a neatly folded blanket in it. Pud has never been in here, but he knows exactly where this is: Granny's bedroom.
Meanwhile, Matilda catches a glance of Titaani being lifted into the sky by Cradefall, maybe fifty feet away on the other side of the log. She is now some 30 feet above the ground. (Titaani may act - to try to break the grapple or try something else. Everyone else may act, too!)
Matilda picks up the jar of moths then hefts it at the tiny dragon.
Attack: 17 Damage: 1
Horatio sees Matilda throwing the jat of Moths and asks, "Were they evil or something?"
Pud waves his hands frantically trying to shush the party. He points at the decrepit dollhouse and does his best with hand gestures and ugly faces to indicate that Granny might be in there sleeping.
DM: how large is this room? Would there be enough room to cast flaming sphere and use a bonus action to ram it into the dollhouse?
Pronouns: he/him/his
Pud - lvl 7 Human Artificer - Alchemist (The Wild Beyond the Witchlight).
Quinn - lvl 4 Human Ranger - Hunter (Phandelver and Below: The Shattered Obelisk)
Ben:
Insight to follow what Pud is trying to communicate: 14
Gerrard Feldren - Human Noble in Ghosts of Saltmarsh
Kerric Brightblade - Elven Warrior in "Apocalypse"
Ben:
Realization dawning on his face, Ben mouths, “To the oven in the kitchen?” and spreads his arms wide, indicating he would be willing to carry the dollhouse.
Gerrard Feldren - Human Noble in Ghosts of Saltmarsh
Kerric Brightblade - Elven Warrior in "Apocalypse"
"What are you doing?" Titaani yells, panicked, at Cradlefall. "Put me down at once! Or...or else...I'll...I'll curse you! And make your life miserable!"
Intimidation: 23
Pronouns: She/her/her's
Currently playing as Titaani Leelathae in The Wild beyond the Witchlight
Pud nods in agreement with Ben. He points at Horatio and Ben motions towards the kitchen. He then pokes himself in the chest and points to the window. He imitates an archer firing a bow and arrow and then flaps his arms like a dragon taking flight.
Pud creeps over to the window. He draws his magical multi tool spell focus and with a flourish and uttering of some magical incantation a magical arrow dripping with acid arcs across the sky towards Cradlefall.
Action: Cast spell acid arrow at Cradlefall. 18 to hit for 13 acid damage.
Pronouns: he/him/his
Pud - lvl 7 Human Artificer - Alchemist (The Wild Beyond the Witchlight).
Quinn - lvl 4 Human Ranger - Hunter (Phandelver and Below: The Shattered Obelisk)
Climbing fully into the bedroom, Matilda grabs the glass jar of moths off the southern windowsill and throws it out the "Yon" window, hoping for a lucky strike on the fleeing dragon.
(Alas, it is a very long shot. Disadvantaged attack roll: 10)
"I'll put you down soon enough," reassures Cradlefall, icily.
Pud steps in behind Matilda and releases a shimmering green arrow from his bowless hands. It hits its target. Cradefall shrieks in rage and pain but continues to rise into the air with Titaani.
(The bedroom is large - it is a circle 40 feet in diameter. Plenty of room for a 5' ball of fire.)
The jar of moths hits a branch and smashes onto the ground on the far side of the log. A cloud of tiny moths is released into the twilit air.
(( If the plan is to carry the dollhouse to the kitchen then Horatio will Help. ))