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Rolling with Difficulty

by Rolling with Difficulty Table
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Latest episodes

  • Hunting Party Q&A: Reel It In

    September 30, 2026 · 1 hr 9 min

    Reunited and off to Karasuthra, but first, a Q&A! ---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…

  • Hunting Party Season 3 Episode 10: "The Eighth Eldest"

    September 18, 2026 · 4 hr 42 min

    Content warning: thalassophobia, body modification In the darkest depths, in the Library of all Knowledge, the Aboleth awaits. Can our Hunting Party prevail? Or will they be swallowed by the deep? ---Our show contains fantasy violence…

  • Hunting Party Season 3 Episode 9: "Clams and Consequence"

    September 11, 2026 · 4 hr 25 min

    The final clams left to place, the Hunting Party enjoys a suspiciously calm series of deposits. This false security cannot last, and as the day ends, the reef looms. It's time to descend beneath the waves... ---Our show contains fantasy…

  • We're Level Fifteen!

    September 7, 2026 · 13 min

    Better belated than never! The party will need every advantage they can get to slay the Aboleth, so Austin graciously lent us a level-up. ---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13…

  • Hunting Party Season 3 Episode 8: "Black Swan"

    September 4, 2026 · 4 hr 36 min

    The clam jam continues as the Hunting Party moves on to more sources of water in Brux. Next up, the Wells and the Synod. Old grudges rear their heads in the latter, will the Swanmays prove friends or foes for our Unicorn Knights? ---Our…

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  • Hunting Party Season 3 Episode 7: "Storm's Edge"

    August 28, 2026 · 4 hr 27 min

    Clams in hand, the Hunting Party sets off to cleanse the waters and cut off their foe's means of escape. Brux is vast, but our heroes move quickly, and perhaps secure aid from some familiar faces along the way... ---Our show contains…

  • Hunting Party Season 3 Episode 6: "Twisted Fates"

    August 21, 2026 · 4 hr 9 min

    Content Warning: Character Conflict, Character Death The fractured party splits only further. As each Knight loses themselves in their own obsessions, will they remember to come together for the sake of the Beastlands? ---Our show contains…

  • Hunting Party Q&A: Gone Fishin'

    August 12, 2026 · 58 min

    The party is split but the cast is together! We answer your questions in our mid-season Q&A! ---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!--- VR-LA and Vhas enamel pins available…

  • Hunting Party Season 3 Episode 5: "Seer Astray"

    August 7, 2026 · 2 hr 52 min

    Alone again, Katya is drawn by the threads of destiny towards the Prowl. Who, or what, awaits the Seer Stray there? ---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!--- Thank you to…

  • Hunting Party Season 3 Episode 4: "Foul Tides"

    July 31, 2026 · 4 hr 22 min

    One wizard poorer, the remaining Unicorn Knights resolve to focus on their quest. The bivalves wait for no one, but they are not the only ones lurking in the Sessile Pools... ---Our show contains fantasy violence (and the occasional foul…

  • Hunting Party Season 3 Episode 3: "Reflections: Part 2"

    July 24, 2026 · 2 hr 39 min

    Garou is dead, but if the party has their way it won't be for long. His life is not simply in the hands of Kireek however, and as great forces tangle for his mortal soul it is Garou who must decide if he stays or goes. Regardless of the…

  • Hunting Party Season 3 Episode 2: "Reflections: Part 1"

    July 17, 2026 · 4 hr 34 min

    Content Warning: Character Death In search of a solution to the Aboleth's toxic waters, the Hunting Party makes for the refuge of the Gnamma. Across the desert's sands waits salvation, but will it be waiting for our heroes? Or will it test…

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About the show

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!