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PODCAST

Rolling with Difficulty

Rolling with Difficulty Table

Throughout the Planescape there are countless wars between good and evil, lawful and chaotic. Forces of great power shift the very nature of reality. These are not their stories... Join Rolling with Difficulty as we explore the Planescape, following adventurers out on the Astral Sea, on the streets of the City of Doors, and beyond! Every episode of this D&D 5e actual play podcast follows a different entry in our adventures, and are intended to be watched in any order your heart desires. Follow the

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All Episodes

149:30

Rolling with Difficulty Presents: "Jungle Jammed!"

Rolling with Difficulty ·

2025/10/31

Content Warning: Cartoon ViolenceEnter the rad dimension! In this Slugblaster adventure our tubular team of teens find themselves a heck of a lot closer to their favorite games than expected. Can they combo their way back to the real world? And just how many nachos can one teen consume? Find out all this and more in Jungle Jammed!---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Burnt Cook Book Party! Check

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60:22

Hunting Party Q&A: Picking Up the Trail

Rolling with Difficulty ·

2025/09/24

After a successful season of Beastland antics, the crew gets together to answer your hardest-hitting questions!---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Rolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/6uAycwAhy6Merch:Redbubble: https://www.redbubble.com/people/RWDPodcast/shop?asc=uContact the Pod:rollwithdifficulty@gmail.comTwitter: @rollwdifficultyInstagram:

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192:47

Hunting Party Season 1 Episode 10: "Eyes Open"

Rolling with Difficulty ·

2025/09/12

Content Warning: Party Conflict, Body ModificationSecrets revealed, the Hunting Party resumes their chase of Trystine's cousin. But they are not the only seekers in the Beastlands, and it's time some eyes were opened... ---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Twice Rolled Tales! Check them out here:https://linktr.ee/twicerolledtaleshttps://www.twicerolledtales.com/YouTube:

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254:18

Hunting Party Season 1 Episode 9: "Incubation"

Rolling with Difficulty ·

2025/09/05

Content Warning: Entomophobia, Creature Body ModificationAfter a brief respite, the Hunting Party is forced face-to-face with the final note on their map. Beyond the trees stripped bare, a reunion awaits...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Burnt Cook Book Party! Check them out here:www.BCBParty.comEpisode One "Kill Santa":

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224:26

Hunting Party Season 1 Episode 8: "Passing the Tusk"

Rolling with Difficulty ·

2025/08/29

The hunt continues, and after a brief detour to drop of the Warden somewhere safe, the Party enters the Domain of the Boar Lord. Her domain encroaches, but just who is leading the charge?---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---VR-LA and Vhas enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty

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255:53

Hunting Party Season 1 Episode 7: "Life and Limb"

Rolling with Difficulty ·

2025/08/22

Content Warning: Cannibalism, ArachnophobiaFinally taking a moment's respite, the Hunting Party regroups at the Grove of the Unicorn before heading back out into the Beastlands. Their prey? A missing Warden, hopefully to be found in one piece...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---VR-LA and Vhas enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyThank you to

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281:51

Hunting Party Season 1 Episode 6: "Belly of the Beast"

Rolling with Difficulty ·

2025/08/15

Content Warning: Entomophobia, Austin is Gross, Decay, These bugs wanna put eggs in thingsNewly assembled, the Hunting Party follows the stench on the wind in pursuit of their first prey. Can this rag-tag group find common ground? Or will the belly of the beast prove too much for the Beastland's newest heroes?---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---VR-LA and Vhas enamel pins available now! Order yours while supplies

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61:05

Hunting Party Q&A: Into the Wild

Rolling with Difficulty ·

2025/08/06

We're halfway through the first season of Hunting Party! The cast gets together and answers the hardest hitting questions about our new crew of hapless heroes.---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Rolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/6uAycwAhy6Merch:Redbubble: https://www.redbubble.com/people/RWDPodcast/shop?asc=uContact the

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12:18

We're Level Twelve!

Rolling with Difficulty ·

2025/08/04

The Hunting Party is assembled and ready to level up! Let's see what these creatures of habit pick in this quick bonus before the adventures resume.---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Rolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/6uAycwAhy6Merch:Redbubble: https://www.redbubble.com/people/RWDPodcast/shop?asc=uContact the

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272:44

Hunting Party Season 1 Episode 5: "Paths Converge"

Rolling with Difficulty ·

2025/08/01

Content Warning: Graphic Violence, Entomophobia, Austin is Gross, PC ConflictOne by one our heroes gather, all on the trail of a shared foe. As their respective hunts draw to a close, Katya, Kireek, Garou, and Trystine may soon find they were not the only ones searching in the Beastland. Can they find a way to work together? Will they form the Hunting Party?---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at

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156:30

Hunting Party Season 1 Episode 4: "Fury of the Frost"

Rolling with Difficulty ·

2025/07/25

Content Warning: Frostbite Trystine has always lived in the safety of her Grandmother's looming shadow, but when a massive creature steals the most precious treasure of her home she risks it all to give chase. Just how far will this hunt take the Fury of the Frost...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Rolls Untold! Check them out here:YouTube: https://www.youtube.com/@RollsUntoldTwitch:

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162:49

Hunting Party Season 1 Episode 3: "Bloodied Mask of...

Rolling with Difficulty ·

2025/07/18

Content Warning: Austin and Wally are Gross, NPC Murder, ArachnophobiaFor the Bloodied Mask of Malar, no creature can escape his hunt. As one falls, a new prey takes it's place, and Garou finds himself on the trail of something aberrant in the Beastlands...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Join the Party! Check them out Here:https://www.jointhepartypod.com/Multitude Podcasts:

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175:35

Hunting Party Season 1 Episode 2: "Seer Stray"

Rolling with Difficulty ·

2025/07/11

Katya has never had a home in the Planescape. When every other place ran her out, she found herself in the Beastlands. The Seer Stray planned to peddle her fortunes as usual, but when a fellow diviner asks her aid, she must answer the call of the wild...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Tabletop Hot Takes! Check them out Here:RSS: https://feeds.captivate.fm/tabletop-hot-takes/Patreon:

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147:01

Hunting Party Season 1 Episode 1: "Scythe and Subjugate"

Rolling with Difficulty ·

2025/07/04

Content Warning: Surgery/Body ModificationFreshly escaped from mindflayer captivity, Kireek the Scythe and Subjugate finds himself in the company of a Unicorn Knight. Their joint goal, purge an aberration from the Beastlands. If they survive the encounter, that will be a victory indeed...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends at Comic Aurora! Preorder your copy

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280:06

Rolling with Difficulty Presents: "Do Or Die"

Rolling with Difficulty ·

2025/06/13

Content Warning: Emotional Distress, Parental Death, Parental Neglect, Drug Addiction/Use, Divorce, Catharsis (We Promise!)When six old friends find themselves pulled into the world of their high school TTRPG game, they'll face foes fantastical and familiar. Old wounds reopen as they find every obstacle pulled from their real lives, pushing on the trials they've faced since graduating. Will they process their emotions and unite to escape? Or have the ravages of time pushed them too far

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338:27

Rolling with Difficulty Presents: "Search for Oloranwë"

Rolling with Difficulty ·

2025/05/16

After helping the B-Team turns up a lead on Kyana's past, the crew journey's through the layers of Arboria to search for Oloranwë. But what awaits at the end of their journey? And what does it mean for their resident monk?---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Rolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/6uAycwAhy6Merch:Redbubble:

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110:45

Open and Shut Q&A: Case Closed

Rolling with Difficulty ·

2025/04/01

Another campaign closed, the cast assembles to answer your questions and bring the secrets of Open and Shut to light!---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Rolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/6uAycwAhy6Merch:Redbubble: https://www.redbubble.com/people/RWDPodcast/shop?asc=uContact the Pod:rollwithdifficulty@gmail.comTwitter:

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291:38

Open and Shut Season 2 Episode 10: "Closed Loop"

Rolling with Difficulty ·

2025/03/21

Their ducks in a row, the detectives of Open and Shut have one final case to solve. The rescue of Evrard begins now. The Loop will be broken.Thank you for listening to the Open and Shut campaign from Rolling with Difficulty! It has been our honor and our joy to have you out on the streets of Sigil with us. The pod will be back this summer for campaign 3, but until then, be sure to follow us on socials and Discord, and stay tuned for one shots and more info about our upcoming third campaign

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302:10

Open and Shut Season 2 Episode 9: "Immortal Peril"

Rolling with Difficulty ·

2025/03/14

In order to clear their names in the eyes of Sigil's more powerful factions, the detectives of Open and Shut must steal from the Dead themselves. Information is gathered, every boon is called in, and the Mortuary looms as the Chronosphere beckons. They cannot fail, but do they have the brains to succeed?---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Kyana and Finbar Pin Pack Available Now! Presale has been extended for one week,

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255:11

Open and Shut Season 2 Episode 8: "Rotten to the Core"

Rolling with Difficulty ·

2025/03/07

Content Warning: Fungi, Disease, Medical Malpractice, Austin is Gross (Again)The detectives of Open and Shut may be reeling from retaliation from the Fortune's Wheel, but they are professionals, and they have a case. They open investigation into the new mysterious disease on the streets of Sigil, and quickly find the source may be more deeper and more sinister then some rogue flies...Producer Note: We had to re-record the second half of this episode due to major technical difficulties (the

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