Rolling with Difficulty

Rolling with Difficulty

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 tale from the beginning, or jump in along the way, however you listen it's sure to be a wild ride!

Episodes

January 16, 2026 197 mins

Only a day after their encounter with the Beholder at the center of the schemes in the Beastlands, the Hunting Party barely stop to breathe before returning to the cave lair. Will this showdown bring an end to the turbulence in the Happy Hunting Grounds? Or are surprises in store for the newest Unicorn Knights?

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Thank y...

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Content Warning: Cartoon Violence

Enter 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-1...

September 24, 2025 60 mins

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/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:
https://crowdmade.com/collections/rolling-with-difficulty

Contact...

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September 12, 2025 192 mins

Content Warning: Party Conflict, Body Modification

Secrets 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/twiceroll...

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Content Warning: Entomophobia, Creature Body Modification

After 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.com
Episode One "Kill ...

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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-difficu...

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Content Warning: Cannibalism, Arachnophobia

Finally 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:...

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Content Warning: Entomophobia, Austin is Gross, Decay, These bugs wanna put eggs in things

Newly 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 an...

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August 6, 2025 61 mins

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/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

...

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August 4, 2025 12 mins

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/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

https://cro...

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Content Warning: Graphic Violence, Entomophobia, Austin is Gross, PC Conflict

One 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 lan...

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...

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Content Warning: Austin and Wally are Gross, NPC Murder, Arachnophobia

For 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 Her...

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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 He...

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Content Warning: Surgery/Body Modification

Freshly 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 Co...

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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 ...

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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/rollingwithdifficulty

Rolling with Difficu...

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April 1, 2025 110 mins

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/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

https://crowdmade.com/collections/rolling-...

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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...

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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 Finb...

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