Rolling with Difficulty

Rolling with Difficulty

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!

Episodes

June 13, 2025 280 mins

Content Warning: Emotional Distress, Parental Death, Parental Neglect, Drug Addiction/Use, Divorce, Catharsis (We Promise!)

When six old friends find themselves pulled into the world of their high school TTRPG game, they'll face foes fantastical and familiar. Old wounds reopen as they find every obstacle pulled from their real lives, pushing on the trials they've faced since graduating. Will they process their emotions and ...

After helping the B-Team turns up a lead on Kyana's past, the crew journey's through the layers of Arboria to search for Oloranwë. But what awaits at the end of their journey? And what does it mean for their resident monk?

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficu...

Mark as Played
April 1, 2025 110 mins

Another campaign closed, the cast assembles to answer your questions and bring the secrets of Open and Shut to light!

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

Redbubble: https://www.redbubble.com/peopl...

Mark as Played

Their ducks in a row, the detectives of Open and Shut have one final case to solve. The rescue of Evrard begins now. The Loop will be broken.

Thank you for listening to the Open and Shut campaign from Rolling with Difficulty! It has been our honor and our joy to have you out on the streets of Sigil with us. The pod will be back this summer for campaign 3, but until then, be sure to follow us on socials and Discord, and stay...

Mark as Played

In order to clear their names in the eyes of Sigil's more powerful factions, the detectives of Open and Shut must steal from the Dead themselves. Information is gathered, every boon is called in, and the Mortuary looms as the Chronosphere beckons. They cannot fail, but do they have the brains to succeed?

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Kyana and Finb...

Mark as Played

Content Warning: Fungi, Disease, Medical Malpractice, Austin is Gross (Again)

The detectives of Open and Shut may be reeling from retaliation from the Fortune's Wheel, but they are professionals, and they have a case. They open investigation into the new mysterious disease on the streets of Sigil, and quickly find the source may be more deeper and more sinister then some rogue flies...

Producer Note: We had to re-record the ...

Mark as Played
March 6, 2025 6 mins

Delayed in posting as Sophia battles the turbo-cold (and loses on the front of "forgetting the level up existed,") enjoy this little bonus teaser of abilities to come!

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Kyana and Finbar Pin Pack Available Now! Preorder for yourself at:
https://crowdmade.com/collections/rolling-with-difficulty

Special Thank You to Our ...

Mark as Played

Business as usual has resumed and our detectives are back on their regular cases. As they investigate another mysterious illness, they find old enemies are finally making moves, and their "usual" might be anything but...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Kyana and Finbar Pin Pack Available Now! Preorder for yourself at:
https://crowdmade.com/collect...

Mark as Played

After a near-miss with a Death Tyrant and seeing Nix and Nil reunited, the doors of Open and Shut swing open once more to welcome a newcomer to the city. Fally, cleric of Helm, seeks out our dedicated detectives, and brings with them the stern eye of Mt. Celestia....

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Kyana and Finbar Pin Pack Available Now! Preorder fo...

Mark as Played
February 14, 2025 59 mins

We're halfway through the second season, ask us your questions!

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:
Redbubble: https://www.redbubble.com/people/RWDPodcast/shop?asc=u

Contact the Pod:
rollwithdifficulty@gmail.co...

Mark as Played

Content Warning: Austin is Gross (Again)

Facing down the Death Tyrant at the heart of the Mortuary, Oobtaglor and Nix are alone, separated from the rest of Open and Shut. Can they maneuver this situation to their advantage? Will they retrieve the body of Nil? Or will the Dead gain two new companions...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Special Thank You...

Content Warning: Body Horror, Animal Endangerment

After dealing with one complicated sibling relationship, the detectives of Open and Shut turn their attention to the next and begin the search for Nil. Their missing persons will take them to familiar haunts, familiar foes, and yet, uncover brand new threats. Will they find the wayward changeling? Or will this case add four new missing people to the Cage...

---Our show contai...

Mark as Played
January 27, 2025 11 mins

New detective in tow, Open and Shut levels up! Tune into a brief little bonus to find out just what boons they'll gain.

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

Redbubble: https://www.redbubble.com/peo...

Mark as Played

After aiding their escape from the Fortune's Wheel, Oobtaglor Skopun calls in their owed favor of their sibling and the rest of Open and Shut. In order to get this sibling rivalry off-plane, they'll need to call in all manner of devilish favors to find Oobtaglor the younger's missing payload...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Special Thank You to Our...

Mark as Played

Content Warning: Arachnophobia

When the employees of the Rat Cafe go mysteriously missing, only the detectives at Open and Shut can find them! After all, they were the only ones asked to investigate. Along with their newest hire, Nix, they'll delve the sewers of Sigil and beyond to find the city's most beloved residents.

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!-...

Mark as Played

Following their bittersweet victory over the Grixit, the detectives of Open and Shut are back to their usual duties (and researching some personal projects as they do). Striking a deal with the Planar Trade Consortium brings with it a new mystery on familiar ground, familiar faces, and a new investigator to shake up Open and Shut's status quo...

Producer Note: Hi guys! Thanks for listening. We had to roll with some technica...

Content Warning: Insects

In the name of TTRPG antics, we'll punish you! In this special one-shot adventure we try out the system Girl By Moonlight and dive into the town of Magnolia. Here the Heartwood Coven, our cast of witchy magical girls, defend the denizens from the goonish forces who threaten to steal their very essence. Can they thwart the villains once more? Can they look cute AND fight crime?

---Our show contains f...

Mark as Played
September 23, 2024 109 mins

This episode originally aired as a YouTube Livestream!

Season One of "Open and Shut" done, the cast gathers to answer your questions! 

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

Redbubble: https://www.red...

Mark as Played
September 13, 2024 233 mins

Content Warning: Character Death

Hot on the trail of the Grixitt, Evrard and the rest of Open and Shut find themselves descending deep below the city. Away from the watchful eyes of the Dabu and the safety of their cozy office, a final showdown begins. Will they bring an end to this portal-closing undead's reign of terror? What will is cost to balance the scales?

---Our show contains fantasy violence (and the occasional foul...

Mark as Played
September 9, 2024 13 mins

In the midst of our lates adventure, the crew takes a break to level up! Hope these new powers will get to wait a season to see some use...
 
---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/6uAycwAhy6

Merch:

Redbubble: ...

Mark as Played

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