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Rolling with Difficulty

Rolling with Difficulty

By: Rolling with Difficulty Table
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Summary
 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!© 2026 Rolling with Difficulty Table
Episodes
  • Rolling with Difficulty Presents: "Journey of the Pennypack"

    Rolling with Difficulty Presents: "Journey of the Pennypack"
    Nov 6 2026
    Go little to go big as Rolling with Difficulty tries out Humblewood! With special guests Olivia and JoCat, Red and Austin enter Sophia's tiniest adventure as they set off to find a new home for the Pennypack. Will they be successful? After all, the world is full of many dangers for creatures so small...---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---Dani enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:rollwithdifficulty@gmail.comRSS Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Game Master - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckSer Gareth - JoCatYouTube: https://www.youtube.com/c/JoCatTwitch: https://www.twitch.tv/jocatBluesky: @jocat.netTheodore - OliviaInstagram: @o.k.rosArt Instagram: @oliviarosartsRolls Untold: @rollsuntoldElwen the Shepherd - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setLakha - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by SophiaBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusicFeatured Tracks:Hunt Downtime ThemeHunt Battle Theme ★ Support this podcast on Patreon ★
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    2 hrs and 2 mins
  • Hunting Party Q&A: Reel It In

    Hunting Party Q&A: Reel It In
    Sep 30 2026

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

    Rolling with Difficulty Patreon:
    patreon.com/rollingwithdifficulty

    Rolling with Difficulty Discord:
    https://discord.gg/8c9e4xhUKy

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

    Contact the Pod:
    rollwithdifficulty@gmail.com
    RSS Feed: https://rollingwithdifficultypod.transistor.fm/
    Youtube: https://www.youtube.com/c/RollingwithDifficulty
    Instagram: @rollwithdifficulty
    BlueSky: @rollwithdifficulty.bsky.social
    Tik Tok: @rollwithdifficulty

    Cast:
    Dungeon Master - Austin Funk
    BlueSky: @atthefunk.bsky.social
    The Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+set

    Katya - Sophia Ricciardi
    BlueSky: @sophiekay.bsky.social
    Instagram: @_sophie_kay
    Moviestruck: https://moviestruck.transistor.fm/
    Patreon: https://www.patreon.com/moviestruck

    Trystine - OSP Red
    BlueSky: @overlysarcastic.bsky.social
    Instagram: @overly.sarcastic.productions
    Overly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/

    Kireek - Noir
    BlueSky: @noirgalaxies.bsky.social
    Instagram: @noirgalaxies

    Garou - Wally
    BlueSky: @wallydraws.bsky.social
    Instagram: @stuckinspace
    Portfolio: https://ghost_astronaut.artstation.com/

    Want to send us snail mail? Use this Address:
    Austin Funk
    1314 5th Ave
    PO Box # 1163
    Bay Shore NY 11706

    Character Art by @stuckinspace
    Background Art by @tanukimi.s

    Music by: Dominic Ricciardi
    https://soundcloud.com/dominicricciardimusic

    ★ Support this podcast on Patreon ★
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    1 hr and 9 mins
  • Hunting Party Season 3 Episode 10: "The Eighth Eldest"

    Hunting Party Season 3 Episode 10: "The Eighth Eldest"
    Sep 18 2026
    Content warning: thalassophobia, body modificationIn 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 (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends over at Twice Rolled Tales! Check them out:https://www.twicerolled.com/Patreon: patreon.com/twicerolledtalesDani enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:rollwithdifficulty@gmail.comRSS Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Dungeon Master - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setKatya - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckTrystine - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Kireek - NoirBlueSky: @noirgalaxies.bsky.socialInstagram: @noirgalaxiesGarou - WallyBlueSky: @wallydraws.bsky.socialInstagram: @stuckinspacePortfolio: https://ghost_astronaut.artstation.com/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by @stuckinspaceBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusicFeatured Tracks:Hunting Party ThemeBig BattleWhen Will the Beast Land?The Beast Has LandedFinal Battle ★ Support this podcast on Patreon ★
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    4 hrs and 42 mins
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I love these guys so much. They make it fun to listen to and it's always super enjoyable. Austin is a great GM and the players are excellent.

love them

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As ridiculous as you'd expect. Very worth the listen. Hope to see more one shots in the future.

The feels! Love it looking forward to more.

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