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
Pinned
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...
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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
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
This Friday enter the rad dimension as Rolling with Difficulty kick-flips into Slugblaster! With @sophiekay.bsky.social at the wheel we've got a gaggle of tubular teens for you to meet, so tune in Friday for all the arcade antics!
Check the thread to meet our ABSOLUTELY STACKED cast! Cowabunga! (🧵)
Check the thread to meet our ABSOLUTELY STACKED cast! Cowabunga! (🧵)
October 27, 2025 at 4:19 PM
This Friday enter the rad dimension as Rolling with Difficulty kick-flips into Slugblaster! With @sophiekay.bsky.social at the wheel we've got a gaggle of tubular teens for you to meet, so tune in Friday for all the arcade antics!
Check the thread to meet our ABSOLUTELY STACKED cast! Cowabunga! (🧵)
Check the thread to meet our ABSOLUTELY STACKED cast! Cowabunga! (🧵)
We have the coolest fans
Drawings of the hunting party of @rollwithdifficulty.bsky.social that I never posted
#myart #rollingwithdifficulty
1/3
#myart #rollingwithdifficulty
1/3
October 12, 2025 at 11:00 PM
We have the coolest fans
Reposted by Rolling with Difficulty
It is finally time to start sharing my @rollwithdifficulty.bsky.social tarot deck. Over two years of work but Major Arcana is down to one card to finish and started planning Minor Arcana. Will probably post a card every Saturday.
#rollingwithdifficulty
#rwd
#fanart
#peraspera
#customtarot
#rollingwithdifficulty
#rwd
#fanart
#peraspera
#customtarot
October 11, 2025 at 9:33 PM
It is finally time to start sharing my @rollwithdifficulty.bsky.social tarot deck. Over two years of work but Major Arcana is down to one card to finish and started planning Minor Arcana. Will probably post a card every Saturday.
#rollingwithdifficulty
#rwd
#fanart
#peraspera
#customtarot
#rollingwithdifficulty
#rwd
#fanart
#peraspera
#customtarot
We're live! Come join the (Hunting) Party for our post-season Q&A: www.youtube.com/live/dIlVAyP...
Hunting Party Q&A: Picking Up the Trail
YouTube video by Rolling with Difficulty
www.youtube.com
September 18, 2025 at 11:01 PM
We're live! Come join the (Hunting) Party for our post-season Q&A: www.youtube.com/live/dIlVAyP...
Tonight on our YouTube channel, the Hunting Party post-season Q&A! The cast will be live at 7pm EST and taking your questions from chat all about the new campaign. Can't join live? Email in your Qs ahead of time and catch us in the VOD.
September 18, 2025 at 2:02 PM
Tonight on our YouTube channel, the Hunting Party post-season Q&A! The cast will be live at 7pm EST and taking your questions from chat all about the new campaign. Can't join live? Email in your Qs ahead of time and catch us in the VOD.
So close! If you saw this cool project and thought “oh, nice, I’ll back it later…” Guess what? It’s later! Help get this Kickstarter across the finish line for our friends at 5 GMs!
‼️ WE ARE 85% FUNDED AND HAVE LESS THAN 48 HOURS TO GO ON OUR KICKSTARTER ‼️
We are SO freaking close to our goal. Kickstarter is all or nothing, so if we reach our goal, we fund! If not, then we don’t. Help us reach it before 9am on Thursday!!
🔗 www.kickstarter.com/projects/5gm...
We are SO freaking close to our goal. Kickstarter is all or nothing, so if we reach our goal, we fund! If not, then we don’t. Help us reach it before 9am on Thursday!!
🔗 www.kickstarter.com/projects/5gm...
September 16, 2025 at 5:15 PM
So close! If you saw this cool project and thought “oh, nice, I’ll back it later…” Guess what? It’s later! Help get this Kickstarter across the finish line for our friends at 5 GMs!
The Hunting Party is hot on the trail of Trystine's wayward cousin, but they are not the only force with an interest in silver in the Beastlands...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/eaa856c9
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/eaa856c9
Hunting Party Season 1 Episode 10: "Eyes Open" | Rolling with Difficulty | Episode 10
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 ...
share.transistor.fm
September 12, 2025 at 4:00 PM
The Hunting Party is hot on the trail of Trystine's wayward cousin, but they are not the only force with an interest in silver in the Beastlands...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/eaa856c9
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/eaa856c9
Our heroes (and also Garou) are looking great!
September 10, 2025 at 3:44 PM
Our heroes (and also Garou) are looking great!
Get in on this while there’s still time! Help our friends make some dope shit (and also then we get to play more games with them!)
11 DAYS LEFT!! BACK OUR KICKSTARTER TODAY!!!
⛺️🌲⛺️ OUR KICKSTARTER FOR SEASON 5 IS LIVE NOW! 🌲⛺️🌲
From Inside the Tent is our 5th podcast season and will be our most ambitious yet. Join three friends as they roadtrip across the U.S. in 1987, encountering strange happenings along the way.
🔗 www.kickstarter.com/projects/5gm...
From Inside the Tent is our 5th podcast season and will be our most ambitious yet. Join three friends as they roadtrip across the U.S. in 1987, encountering strange happenings along the way.
🔗 www.kickstarter.com/projects/5gm...
September 7, 2025 at 2:08 AM
Get in on this while there’s still time! Help our friends make some dope shit (and also then we get to play more games with them!)
Reposted by Rolling with Difficulty
Don’t they make a nice lineup? VR-LA and Vhas are still available if you’re looking to expand your party!
September 6, 2025 at 10:06 PM
Don’t they make a nice lineup? VR-LA and Vhas are still available if you’re looking to expand your party!
Only one section of the map remains to investigate, but our hunting Party are not the only ones taking an interest in the Beastlands...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/93bb09fc
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/93bb09fc
Hunting Party Season 1 Episode 9: "Incubation" | Rolling with Difficulty | Episode 9
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 awa...
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September 5, 2025 at 4:01 PM
Only one section of the map remains to investigate, but our hunting Party are not the only ones taking an interest in the Beastlands...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/93bb09fc
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/93bb09fc
Now those are some shiny boys!
Got my boys from @rollwithdifficulty.bsky.social they are so cuuuute!
If i may..... request..... a re-release of Kyana and Finbar at some point? I wasn't able to get them with their run. 🥺
Can't wait to see the captain!!!
If i may..... request..... a re-release of Kyana and Finbar at some point? I wasn't able to get them with their run. 🥺
Can't wait to see the captain!!!
September 5, 2025 at 3:31 PM
Now those are some shiny boys!
Returning the rescued Warden to safety, the Hunting Party sets their sights on an encroaching domain, and the usurpers leading the charge...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/70717b1a
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/70717b1a
Hunting Party Season 1 Episode 8: "Passing the Tusk" | Rolling with Difficulty | Episode 8
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 c...
share.transistor.fm
August 29, 2025 at 4:00 PM
Returning the rescued Warden to safety, the Hunting Party sets their sights on an encroaching domain, and the usurpers leading the charge...
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/70717b1a
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/70717b1a
After a brief respite at the Grove of the Unicorn, the Hunting Party heads on the trail of a wayward Warden. What woe could have befallen this Beastlands native?
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0a3516b4
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0a3516b4
Hunting Party Season 1 Episode 7: "Life and Limb" | Rolling with Difficulty | Episode 7
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 ...
share.transistor.fm
August 22, 2025 at 4:00 PM
After a brief respite at the Grove of the Unicorn, the Hunting Party heads on the trail of a wayward Warden. What woe could have befallen this Beastlands native?
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0a3516b4
The pod is available on all major platforms, YouTube, or direct from our RSS feed at: share.transistor.fm/s/0a3516b4
Reposted by Rolling with Difficulty
My boys arrived! The VR-LA and Vhas pins! The quest to assemble the whole Per Aspera crew continues
You can get your own pins from the @rollwithdifficulty.bsky.social Crowdmade store. Only available while supplies last: crowdmade.com/collections/...
You can get your own pins from the @rollwithdifficulty.bsky.social Crowdmade store. Only available while supplies last: crowdmade.com/collections/...
August 21, 2025 at 8:42 PM
My boys arrived! The VR-LA and Vhas pins! The quest to assemble the whole Per Aspera crew continues
You can get your own pins from the @rollwithdifficulty.bsky.social Crowdmade store. Only available while supplies last: crowdmade.com/collections/...
You can get your own pins from the @rollwithdifficulty.bsky.social Crowdmade store. Only available while supplies last: crowdmade.com/collections/...
Check out our friends at 5 GMs and what they’re working on! It’s going to be awesome (and also we at RWD get to be a part of it?)!
⛺️🌲⛺️ OUR KICKSTARTER FOR SEASON 5 IS LIVE NOW! 🌲⛺️🌲
From Inside the Tent is our 5th podcast season and will be our most ambitious yet. Join three friends as they roadtrip across the U.S. in 1987, encountering strange happenings along the way.
🔗 www.kickstarter.com/projects/5gm...
From Inside the Tent is our 5th podcast season and will be our most ambitious yet. Join three friends as they roadtrip across the U.S. in 1987, encountering strange happenings along the way.
🔗 www.kickstarter.com/projects/5gm...
August 20, 2025 at 11:08 PM
Check out our friends at 5 GMs and what they’re working on! It’s going to be awesome (and also we at RWD get to be a part of it?)!