Rolling with Difficulty
@rollwithdifficulty.bsky.social
Four idiots in the Beastlands!
Rolling with Difficulty is a D&D Planescape actual play adventure. The podcast is available now on all fine audio platforms and at youtube.com/@RollingwithDifficulty
Rolling with Difficulty is a D&D Planescape actual play adventure. The podcast is available now on all fine audio platforms and at youtube.com/@RollingwithDifficulty
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Hunting Party Season 2 Episode 5: "Monkey Business: Part 2" | Rolling with Difficulty | Episode 5
The lair of the Ape Lord looms and the only way to the root of this problem is through. Hoards of primates stand in their way, but that has never stopped the Hunting Party from reaching their quarry b...
share.transistor.fm
The lair of the Ape Lord looms, and with it an untold number of primate protectors. The quarry is set, the Hunting Party must put this monkey business to rest...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/868cb752
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/868cb752
The lair of the Ape Lord looms, and with it an untold number of primate protectors. The quarry is set, the Hunting Party must put this monkey business to rest...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/868cb752
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/868cb752
Hunting Party Season 2 Episode 5: "Monkey Business: Part 2" | Rolling with Difficulty | Episode 5
The lair of the Ape Lord looms and the only way to the root of this problem is through. Hoards of primates stand in their way, but that has never stopped the Hunting Party from reaching their quarry b...
share.transistor.fm
February 13, 2026 at 4:59 PM
The lair of the Ape Lord looms, and with it an untold number of primate protectors. The quarry is set, the Hunting Party must put this monkey business to rest...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/868cb752
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/868cb752
The troubles never stop in the Beastlands as the Hunting Party turns their attention to the center of the brewing war. What draws the Bears, Lizards, and Apes to the crater...?
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/2109a1d0
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/2109a1d0
Hunting Party Season 2 Episode 4: "Monkey Business: Part 1" | Rolling with Difficulty | Episode 4
Preparations made, it's time for the Hunting Party to investigate the cause of all this conflict in the Beastlands. They are not the only party interested in the central point of interest however, and...
share.transistor.fm
February 6, 2026 at 5:00 PM
The troubles never stop in the Beastlands as the Hunting Party turns their attention to the center of the brewing war. What draws the Bears, Lizards, and Apes to the crater...?
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/2109a1d0
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/2109a1d0
Reposted by Rolling with Difficulty
There’s less than a week until PUNDERWORLD launches on Kickstarter! Venture into a land of wit, wordplay, and a whole lot of Dad jokes, where the difference between “literally” and “figurately” can be the difference between life and death.
Pre-Save The Campaign: www.kickstarter.com/projects/twi...
Pre-Save The Campaign: www.kickstarter.com/projects/twi...
Coming soon: Punderworld: A Tabletop Wordplaying Game
A game of puns to inflict on your friends.
www.kickstarter.com
February 4, 2026 at 10:43 PM
There’s less than a week until PUNDERWORLD launches on Kickstarter! Venture into a land of wit, wordplay, and a whole lot of Dad jokes, where the difference between “literally” and “figurately” can be the difference between life and death.
Pre-Save The Campaign: www.kickstarter.com/projects/twi...
Pre-Save The Campaign: www.kickstarter.com/projects/twi...
Recovering from an encounter with the would-be Ant Lord, the party takes a moment to tie up some loose ends. Mysterious goals, personal bonds, all drawn further into the fold...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/38880321
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/38880321
Hunting Party Season 2 Episode 3: "Tales of the Beastlands" | Rolling with Difficulty | Episode 3
Fresh off their victory over the would-be Ant Lord, the Hunting Party ties up loose ends. Some traverse the land in pursuit of their own mysterious goals, others forge new bonds, but all find themselv...
share.transistor.fm
January 30, 2026 at 5:00 PM
Recovering from an encounter with the would-be Ant Lord, the party takes a moment to tie up some loose ends. Mysterious goals, personal bonds, all drawn further into the fold...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/38880321
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/38880321
Reposted by Rolling with Difficulty
Missed the recent Ancestries of the Timescape Game Jam deadline but @atthefunk.bsky.social and I would love to share our would be submission.
An upside to missing the deadline, is that we could push outside the rules of the jam. Full PDF is now available:
platinumstarsgames.itch.io/draw-steel-a...
An upside to missing the deadline, is that we could push outside the rules of the jam. Full PDF is now available:
platinumstarsgames.itch.io/draw-steel-a...
January 28, 2026 at 5:04 PM
Missed the recent Ancestries of the Timescape Game Jam deadline but @atthefunk.bsky.social and I would love to share our would be submission.
An upside to missing the deadline, is that we could push outside the rules of the jam. Full PDF is now available:
platinumstarsgames.itch.io/draw-steel-a...
An upside to missing the deadline, is that we could push outside the rules of the jam. Full PDF is now available:
platinumstarsgames.itch.io/draw-steel-a...
With the colony on their doorstep, their next prey is clear. The Hunting Party's greatest foe, ants!
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0c1818e1
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0c1818e1
Hunting Party Season 2 Episode 2: "Queen's Judgement" | Rolling with Difficulty | Episode 2
Content Warning: Entomophobia, Fungi and RotThe Beholder out of sight, the Hunting Party turns their attention to the vestiges of his work across the Beastlands. First up, the new colony knocking on t...
share.transistor.fm
January 23, 2026 at 4:04 PM
With the colony on their doorstep, their next prey is clear. The Hunting Party's greatest foe, ants!
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0c1818e1
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0c1818e1
Just in time for new problems in the Beastlands, the Hunting Party gets stronger! Check out all the new spells and stats in this level-up bonus.
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/b37fa7b1
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/b37fa7b1
We're Level Thirteen! | Rolling with Difficulty | Episode 13
Just in time for new trouble in the Beastlands, the Hunting Party levels up!---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---VR-LA and Vhas en...
share.transistor.fm
January 19, 2026 at 5:07 PM
Just in time for new problems in the Beastlands, the Hunting Party gets stronger! Check out all the new spells and stats in this level-up bonus.
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/b37fa7b1
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/b37fa7b1
After a brief respite, the Party is back on the trail of the meddlesome Beholder. But while they rested his eye stalks have not been idle, and new trouble brews in the Beastlands...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/329f70a5
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/329f70a5
Hunting Party Season 2 Episode 1: "The Brewing Storm" | Rolling with Difficulty | Episode 12
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 ...
share.transistor.fm
January 16, 2026 at 5:00 PM
After a brief respite, the Party is back on the trail of the meddlesome Beholder. But while they rested his eye stalks have not been idle, and new trouble brews in the Beastlands...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/329f70a5
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/329f70a5
Need some tunes to hunt Aberrations in? Never fear, the Beastlands crew is here! First up from our (banger) Hunting Party, Trystine:
January 5, 2026 at 4:52 PM
Need some tunes to hunt Aberrations in? Never fear, the Beastlands crew is here! First up from our (banger) Hunting Party, Trystine:
Return to the Beastlands January 16th with "Hunting Party" season 2! Our crew has been busy finding new fits to impress Beastlords and defeat Beholders in, and @wallydraws.bsky.social found time to draw those fine threads. Stay tuned in the lead-up to the new season for all the crew's new looks (🧵)
January 5, 2026 at 4:50 PM
Return to the Beastlands January 16th with "Hunting Party" season 2! Our crew has been busy finding new fits to impress Beastlords and defeat Beholders in, and @wallydraws.bsky.social found time to draw those fine threads. Stay tuned in the lead-up to the new season for all the crew's new looks (🧵)
Reposted by Rolling with Difficulty
IT'S HERE! The Dice Cabinet: Dice Signaling is out now wherever you get your podcasts!!🌶️🌶️🌶️
Max is joined in the cabinet by by @ameliasom.com, @thedainiac.bsky.social, and @sophiekay.bsky.social to take on their spiciest takes.
Max is joined in the cabinet by by @ameliasom.com, @thedainiac.bsky.social, and @sophiekay.bsky.social to take on their spiciest takes.
December 31, 2025 at 9:10 PM
IT'S HERE! The Dice Cabinet: Dice Signaling is out now wherever you get your podcasts!!🌶️🌶️🌶️
Max is joined in the cabinet by by @ameliasom.com, @thedainiac.bsky.social, and @sophiekay.bsky.social to take on their spiciest takes.
Max is joined in the cabinet by by @ameliasom.com, @thedainiac.bsky.social, and @sophiekay.bsky.social to take on their spiciest takes.
“And how did VR-LA feel? When you first met him?”
“…Lonely.”
Read the rest of the interview between Catriona and some old friends on our patreon now!
“…Lonely.”
Read the rest of the interview between Catriona and some old friends on our patreon now!
December 31, 2025 at 10:36 PM
“And how did VR-LA feel? When you first met him?”
“…Lonely.”
Read the rest of the interview between Catriona and some old friends on our patreon now!
“…Lonely.”
Read the rest of the interview between Catriona and some old friends on our patreon now!
Reposted by Rolling with Difficulty
🦕💀 NEW BEYOND THE WITCHING HOUR 💀🦕
This week's oneshot, "Esurient", GM'd by Adam Gonzales (@adam5gms.bsky.social) from follows a group of people who get trapped in a research facility after a power outage, forcing them to stand against an experiment born of mankind's hubris.
#ttrpg
This week's oneshot, "Esurient", GM'd by Adam Gonzales (@adam5gms.bsky.social) from follows a group of people who get trapped in a research facility after a power outage, forcing them to stand against an experiment born of mankind's hubris.
#ttrpg
December 18, 2025 at 6:57 PM
🦕💀 NEW BEYOND THE WITCHING HOUR 💀🦕
This week's oneshot, "Esurient", GM'd by Adam Gonzales (@adam5gms.bsky.social) from follows a group of people who get trapped in a research facility after a power outage, forcing them to stand against an experiment born of mankind's hubris.
#ttrpg
This week's oneshot, "Esurient", GM'd by Adam Gonzales (@adam5gms.bsky.social) from follows a group of people who get trapped in a research facility after a power outage, forcing them to stand against an experiment born of mankind's hubris.
#ttrpg
In Philly this weekend? Come check out Sophia in her natural environment, using TTRPGs to pitch the most festive flick of all time
THIS SATURDAY! @plusoneexp.bsky.social and I are throwing a special holiday zine swap and Cookie Party at Unity Java in Philly!
Come hang out, swap goodies, meet some Philly games friends, and then join us for a special @partyofonepodcast.bsky.social recording with @sophiekay.bsky.social at 7pm!
Come hang out, swap goodies, meet some Philly games friends, and then join us for a special @partyofonepodcast.bsky.social recording with @sophiekay.bsky.social at 7pm!
December 18, 2025 at 10:04 PM
In Philly this weekend? Come check out Sophia in her natural environment, using TTRPGs to pitch the most festive flick of all time
“Yeah, you followed the snake. Why? You’re not a messenger, and you’re the farthest thing from a town guard.” Alexandros put down the mug. “And it’s been a long time since we all played hero.”
“Longer for some of us,” said Hakon.
Read the rest on our patreon now, Oto’s Clients tier and up!
“Longer for some of us,” said Hakon.
Read the rest on our patreon now, Oto’s Clients tier and up!
November 30, 2025 at 8:06 PM
“Yeah, you followed the snake. Why? You’re not a messenger, and you’re the farthest thing from a town guard.” Alexandros put down the mug. “And it’s been a long time since we all played hero.”
“Longer for some of us,” said Hakon.
Read the rest on our patreon now, Oto’s Clients tier and up!
“Longer for some of us,” said Hakon.
Read the rest on our patreon now, Oto’s Clients tier and up!
Today we closed our Redbubble store, and moved all our merch over to Crowdmade! To celebrate our new home, we've launched a new Unicorn Knight Badge design by our very own @wallydraws.bsky.social , and put a 10% discount on everything in the store! Check it out!
crowdmade.com/collections/...
crowdmade.com/collections/...
Rolling with Difficulty Official Merchandise
Welcome to the official merchandise store for Rolling with Difficulty!
crowdmade.com
November 28, 2025 at 3:48 PM
Today we closed our Redbubble store, and moved all our merch over to Crowdmade! To celebrate our new home, we've launched a new Unicorn Knight Badge design by our very own @wallydraws.bsky.social , and put a 10% discount on everything in the store! Check it out!
crowdmade.com/collections/...
crowdmade.com/collections/...
Thank you so much to everyone who stopped by our table this #PAXUnplugged ! It was a pleasure to meet friends old and new in Philly, hopefully we’ll catch each other out on the Astral Sea! Or at least, at the next PAXU
November 24, 2025 at 4:55 PM
Thank you so much to everyone who stopped by our table this #PAXUnplugged ! It was a pleasure to meet friends old and new in Philly, hopefully we’ll catch each other out on the Astral Sea! Or at least, at the next PAXU
#PAXUnplugged day 2! We’re low on prints but high on spirits! Stop on by!
November 22, 2025 at 4:57 PM
#PAXUnplugged day 2! We’re low on prints but high on spirits! Stop on by!
Reposted by Rolling with Difficulty
Bought these fantastic prints from @rollwithdifficulty.bsky.social at #paxunplugged ! They signed them for me and everything! 😁
November 22, 2025 at 4:21 AM
Bought these fantastic prints from @rollwithdifficulty.bsky.social at #paxunplugged ! They signed them for me and everything! 😁
The Oob (and crew) have landed! Stop by Brandland at #PAXUnplugged to say hi and have your mysteries solved
November 21, 2025 at 2:21 PM
The Oob (and crew) have landed! Stop by Brandland at #PAXUnplugged to say hi and have your mysteries solved
Join Oob in the City of Tables as Rolling with Difficulty heads to Brandland at #PAXUnplugged ! In addition to a surprise cameo from one of our dauntless detectives, the cast will be hanging out at a table packed with goodies from across the Planescape. So stop by! And we'll catch you out at PAXU...
November 17, 2025 at 5:29 PM
Join Oob in the City of Tables as Rolling with Difficulty heads to Brandland at #PAXUnplugged ! In addition to a surprise cameo from one of our dauntless detectives, the cast will be hanging out at a table packed with goodies from across the Planescape. So stop by! And we'll catch you out at PAXU...
Congrats to @atthefunk.bsky.social for getting the entire Per Aspera crew in one place (and getting married!) We're so proud of our fearless forever DM, and wish him and his wonderful wife nothing but natural 20s for life!
November 17, 2025 at 5:17 PM
Congrats to @atthefunk.bsky.social for getting the entire Per Aspera crew in one place (and getting married!) We're so proud of our fearless forever DM, and wish him and his wonderful wife nothing but natural 20s for life!
Reposted by Rolling with Difficulty
What's RAD AS HELL and let's me have a PET SUGAR GLIDER?!?!?
Well come throw your quarter down on the "Human Violence 2" arcade cabinet, challenge Dez to a match, and find out in this tubular @rollwithdifficulty.bsky.social one shot.
Well come throw your quarter down on the "Human Violence 2" arcade cabinet, challenge Dez to a match, and find out in this tubular @rollwithdifficulty.bsky.social one shot.
Rolling with Difficulty Presents: "Jungle Jammed!"
YouTube video by Rolling with Difficulty
www.youtube.com
November 4, 2025 at 4:14 PM
What's RAD AS HELL and let's me have a PET SUGAR GLIDER?!?!?
Well come throw your quarter down on the "Human Violence 2" arcade cabinet, challenge Dez to a match, and find out in this tubular @rollwithdifficulty.bsky.social one shot.
Well come throw your quarter down on the "Human Violence 2" arcade cabinet, challenge Dez to a match, and find out in this tubular @rollwithdifficulty.bsky.social one shot.
Reposted by Rolling with Difficulty
Kept thinking about how similar Catriona from Rolling with Difficulty and Crass Carla from Fool's Gold: Sands are that I just had to draw them together
#rollingwithdifficulty #rollingwithdifficultyfanart #foolsgoldsands #dnd #art
#rollingwithdifficulty #rollingwithdifficultyfanart #foolsgoldsands #dnd #art
October 20, 2025 at 9:22 PM
Kept thinking about how similar Catriona from Rolling with Difficulty and Crass Carla from Fool's Gold: Sands are that I just had to draw them together
#rollingwithdifficulty #rollingwithdifficultyfanart #foolsgoldsands #dnd #art
#rollingwithdifficulty #rollingwithdifficultyfanart #foolsgoldsands #dnd #art
Happy Halloween tubular teens! kick-flip in to the rad dimension with our special Slugblaster one-shot, and find out if our crew of arcade lurkers can break the game!
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/47450aa9
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/47450aa9
Rolling with Difficulty Presents: "Jungle Jammed!" | Rolling with Difficulty | Episode
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...
share.transistor.fm
October 31, 2025 at 4:00 PM
Happy Halloween tubular teens! kick-flip in to the rad dimension with our special Slugblaster one-shot, and find out if our crew of arcade lurkers can break the game!
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/47450aa9
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/47450aa9