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
Kireek is ready to replicate any of these tunes for you, Mindflayer impression not included:
January 12, 2026 at 3:02 PM
Kireek is ready to replicate any of these tunes for you, Mindflayer impression not included:
Next up, @noirgalaxies.bsky.social Kireek, now with lore-accurate carpet technology:
January 12, 2026 at 2:59 PM
Next up, @noirgalaxies.bsky.social Kireek, now with lore-accurate carpet technology:
Garou has some songs for when you need to drown out the voice of an evil god in your head, or when it rains!
January 7, 2026 at 5:24 PM
Garou has some songs for when you need to drown out the voice of an evil god in your head, or when it rains!
Next up, @wallydraws.bsky.social brings a lil bad to the crew with the stinkiest Bugbear of all, Garou:
January 7, 2026 at 5:22 PM
Next up, @wallydraws.bsky.social brings a lil bad to the crew with the stinkiest Bugbear of all, Garou:
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:
First up, @overlysarcastic.bsky.social Red as Trystine, who continues to embrace the truth of shorts:
January 5, 2026 at 4:50 PM
First up, @overlysarcastic.bsky.social Red as Trystine, who continues to embrace the truth of shorts:
#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!
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!
Entering the rad dimension for the first time, it's special guests @thejenna.bsky.social and @matthewkrol.nebula.tv as Sleater and Dez!
October 27, 2025 at 4:22 PM
Entering the rad dimension for the first time, it's special guests @thejenna.bsky.social and @matthewkrol.nebula.tv as Sleater and Dez!
Series regulars @overlysarcastic.bsky.social Red, @noirgalaxies.bsky.social , and @wallydraws.bsky.social ollie-in as Ross, Hot Rod, and DLC!
October 27, 2025 at 4:21 PM
Series regulars @overlysarcastic.bsky.social Red, @noirgalaxies.bsky.social , and @wallydraws.bsky.social ollie-in as Ross, Hot Rod, and DLC!
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! (🧵)
Pins are back baby! You can now add enamel versions of Mystra's specialest boy and America's favorite Githyanki to your walls, bags, and more. Head on over to Crowdmade to snag pins of your very own. Supplies are limited, get them before they plane-hop away!
crowdmade.com/collections/...
crowdmade.com/collections/...
August 15, 2025 at 11:42 PM
Pins are back baby! You can now add enamel versions of Mystra's specialest boy and America's favorite Githyanki to your walls, bags, and more. Head on over to Crowdmade to snag pins of your very own. Supplies are limited, get them before they plane-hop away!
crowdmade.com/collections/...
crowdmade.com/collections/...
What does the granddaughter of a dragon listen to? @overlysarcastic.bsky.social Red's playlist has the answers!
Trystine joins the Hunting Party July 4th on Rolling with Difficulty!
Trystine joins the Hunting Party July 4th on Rolling with Difficulty!
July 2, 2025 at 2:13 PM
What does the granddaughter of a dragon listen to? @overlysarcastic.bsky.social Red's playlist has the answers!
Trystine joins the Hunting Party July 4th on Rolling with Difficulty!
Trystine joins the Hunting Party July 4th on Rolling with Difficulty!
On July 4th, @overlysarcastic.bsky.social Red
as Trystine joins the Hunting Party! The legacy of Fury of the Frost emerges in Rolling with Difficulty Campaign 3.
as Trystine joins the Hunting Party! The legacy of Fury of the Frost emerges in Rolling with Difficulty Campaign 3.
June 30, 2025 at 1:50 PM
On July 4th, @overlysarcastic.bsky.social Red
as Trystine joins the Hunting Party! The legacy of Fury of the Frost emerges in Rolling with Difficulty Campaign 3.
as Trystine joins the Hunting Party! The legacy of Fury of the Frost emerges in Rolling with Difficulty Campaign 3.
“Ophelia-
I’ve been keeping an eye out like you asked. Lots of rumors of strange things here in Krigala… I’m going to investigate, but it’s a lot of ground to cover all by ourselves.
We may have our work cut out for us.
-Rhaal”
Rolling with Difficulty: Hunting Party begins this Friday!
I’ve been keeping an eye out like you asked. Lots of rumors of strange things here in Krigala… I’m going to investigate, but it’s a lot of ground to cover all by ourselves.
We may have our work cut out for us.
-Rhaal”
Rolling with Difficulty: Hunting Party begins this Friday!
June 29, 2025 at 1:27 PM
“Ophelia-
I’ve been keeping an eye out like you asked. Lots of rumors of strange things here in Krigala… I’m going to investigate, but it’s a lot of ground to cover all by ourselves.
We may have our work cut out for us.
-Rhaal”
Rolling with Difficulty: Hunting Party begins this Friday!
I’ve been keeping an eye out like you asked. Lots of rumors of strange things here in Krigala… I’m going to investigate, but it’s a lot of ground to cover all by ourselves.
We may have our work cut out for us.
-Rhaal”
Rolling with Difficulty: Hunting Party begins this Friday!
Heed well the words of Malar and listen to Garou's character playlist!
Garou joins the Hunting Party July 4th on Rolling with Difficulty!
Garou joins the Hunting Party July 4th on Rolling with Difficulty!
June 25, 2025 at 2:33 PM
Heed well the words of Malar and listen to Garou's character playlist!
Garou joins the Hunting Party July 4th on Rolling with Difficulty!
Garou joins the Hunting Party July 4th on Rolling with Difficulty!
On July 4th, @wallydraws.bsky.social as Garou joins the Hunting Party! Beware the Bloodied Mask of Malar in Rolling with Difficulty Campaign 3.
June 23, 2025 at 2:15 PM
On July 4th, @wallydraws.bsky.social as Garou joins the Hunting Party! Beware the Bloodied Mask of Malar in Rolling with Difficulty Campaign 3.
Need a soundtrack for your next spell casting session? Check out Katya's character playlist!
Katya joins the Hunting Party July 4th on Rolling with Difficulty!
Katya joins the Hunting Party July 4th on Rolling with Difficulty!
June 18, 2025 at 2:06 PM
Need a soundtrack for your next spell casting session? Check out Katya's character playlist!
Katya joins the Hunting Party July 4th on Rolling with Difficulty!
Katya joins the Hunting Party July 4th on Rolling with Difficulty!
On July 4th, @sophiekay.bsky.social as Katya joins the Hunting Party! The mysterious Seer Stray's last and only choice is to defend the Beastlands in Rolling with Difficulty Campaign 3.
June 16, 2025 at 3:08 PM
On July 4th, @sophiekay.bsky.social as Katya joins the Hunting Party! The mysterious Seer Stray's last and only choice is to defend the Beastlands in Rolling with Difficulty Campaign 3.
A big thank you to @e-johnsen.bsky.social who made us the cutest little guys! It’s always good to see the crew of the Per Aspera again, especially in such adorable form
June 16, 2025 at 1:58 AM
A big thank you to @e-johnsen.bsky.social who made us the cutest little guys! It’s always good to see the crew of the Per Aspera again, especially in such adorable form
Plus, returning to the pod, @sophiekay.bsky.social @wallydraws.bsky.social @overlysarcastic.bsky.social and our fearless GM for Die RPG, @noirgalaxies.bsky.social
June 13, 2025 at 4:23 PM
Plus, returning to the pod, @sophiekay.bsky.social @wallydraws.bsky.social @overlysarcastic.bsky.social and our fearless GM for Die RPG, @noirgalaxies.bsky.social
Meet the cast of our latest one-shot, "Do or Die" a Die RPG adventure! First up are our wonderful guests from @magehandhighfive.bsky.social , Max and Robin!
June 13, 2025 at 4:23 PM
Meet the cast of our latest one-shot, "Do or Die" a Die RPG adventure! First up are our wonderful guests from @magehandhighfive.bsky.social , Max and Robin!
Want to get the vibe of our newest aberration? Check out Kireek's character playlist!
Kireek joins the Hunting Party July 4th on Rolling with Difficulty!
Kireek joins the Hunting Party July 4th on Rolling with Difficulty!
June 11, 2025 at 3:08 PM
Want to get the vibe of our newest aberration? Check out Kireek's character playlist!
Kireek joins the Hunting Party July 4th on Rolling with Difficulty!
Kireek joins the Hunting Party July 4th on Rolling with Difficulty!