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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 the crew of the Per Aspera as they make a living in the expanse of the scape. No job is too odd, no region too remote for this motley crew of adventurers. From the fiery City of Brass to the winding woods of the Feywild, they'll go wherever the day takes them aboard their trusty Spelljammer.

Rolling With Difficulty is a D&D 5e Actual Play podcast which follows the adventures of the crew of the spelljammer Per Aspera, set in a homebrewed mish-mash of the Planescape and Spelljammer settings. There are currently five seasons of the main campaign, and a small handful of one-shots, as well.


Rolling with Difficulty includes examples of:

    General 
  • Alien Geometries: It's mentioned that trying to fly higher in the Astral Sea doesn't really work as the "surface" can only ever be so far away from you.
  • Breather Episode: Joked about in that every time an episode starts like this it so far always ends with a difficult combat.
  • City of Adventure
    • Sigil, the City of Doors, located at the exact center of the multiverse and containing portals to every plane, serves as a Hub City for the crew.
    • Also applies to the City of Brass in the Elemental Plane of Fire, home to the Efreeti and ruled over by the Grand Sultan. Home to massive markets and located at the shore of the Sea of Fire.
    • This also fits Tu'narath, the city of the Githyanki, built on the corpse of a fallen god.
  • Crossover Cosmology: The setting is a mashup of Planescape and Spelljammer, the two crossover cosmologies of D&D. In the first episode, the party finds the corpse of Amaunator, a Faerûnian sun god.
  • Naïve Newcomer: Kyana starts off as this. Also, a bit of Enforced Method Acting, as this is Red's first time playing 5th Edition.
  • People Farms: This is discussed in story to be the origins of the githzerai and the githyanki at the hands of the mind flayers who created them to be psychic slaves. This is also what the mind flayers were doing at the Priory where Kyana was raised.
  • Timey-Wimey Ball: The Astral Sea is stated to have an inconsistent flow of time compared to the various planes. Presumably this is to help handwave travel times somewhat.
  • Unaffected by Spice: It's stated that many fire-resistant creatures don't feel the sting of spices nearly as strongly as everyone else, which makes food on the Elemental Plane of Fire near-intolerably spicy for many visitors.

    Season 1 
Season One began on January 7, 2022, and ended on March 18, 2022.
  • Beard of Evil: The berbalang in Episode 1 has a goatee, causing Red to note that that's how they know they're evil.
  • Firebreathing Diner: When eating at a restaurant in Episode 1, Dani and Kyana have their meals with hot sauce made from a chili that grows in Avernus, the First Hell. Predictably, Kyana is not a fan. She later weaponizes it during the bar fight, taking one of the spicy platters and shoving it in the face of a gnoll.
  • God Is Dead: The party's mission in Episode 1 is to find the decayed corpse of a long-dead minor deity and recover its heart on behalf of Hira, a CollectorOfTheStrange.
  • The Nothing After Death: While cruising across the Astral Sea, Kyana spots a group of Petitioners, souls of the dead who have no god to claim them. They float around without direction, hoping some higher being will take pity on them. Kyana gets a brief existential crisis upon realizing that's how she will end up after death.
  • Shout-Out: While with the Feywilds in Episode 4, Dani & VR-LA, attempt to teach the fey to build traps to better defend their village. During which they directly reference Home Alone and The Lion King 1 ½, which apparently in this world were stage productions.
  • Train Job: The premise of Episode 2 is that the party is sent on a mission to steal coins with mortal souls bound to them — which are the fuel for infernal motorbikes with Soul Powered Engines — from a train that runs through Avernus, the first layer of the nine Hells.
  • You All Meet in an Inn: Lampshaded by the DM. Despite playing across the endlessly vast and wonderful Great Wheel, they still managed to start the game in a tavern.

    Season 2 
Season Two began on July 1, 2022, and ended on September 2, 2022.
  • Birthday Buddies: Excluding Finbar, none of the crew actually know when their birthdays are. Therefore, Finbar shares his birthday with them.
  • Birthday Episode: Episode 4. It's Finbar's (and everybody else's) birthday!
  • Shout-Out: During a combat in Episode 5, the players refer to a duo of Yugoloths as a number of different iconic duos (such as Jesse and James).

    Season 3 
Season Three began on January 6, 2023, and ended on March 17, 2023.
  • The Alcatraz: The Prison of Three Sorrows, a Githyanki prison located in Tu'narath, the Heart of the One in the Void.
  • Arc Words: If they are lost, I shall find them; If they are imprisoned, I shall free them; If they are dead... I shall bury them.
  • The Determinator: VR-LA. He latches on to even the smallest hints about his missing crew and their locations, and once he gets his hands on a Wish Ring? There's no stopping him.

    Season 4 
Season Four began on July 7, 2023, and ended on September 15, 2023.
  • Cacophony Cover Up: During their great escape after the death of Endellion, the sound of VR-LA's Knock spell is covered up by the general pandemonium in... well, Pandemonium.
  • Empty Chair Memorial: At Finbar's wedding, when VR-LA sits with his former crew, they pour an extra drink. For MR-SN.
  • Enemies List: Joked about in Episode 5. VR-LA starts making a list of so-called loose ends that could interrupt the wedding, but has to stop, "because the enemy list ends up exceeding the guest list."
  • Retirony: Joked about with Finbar, who has many close calls with death right before getting married and leaving the crew.
  • Wham Episode: Episode 8 is entirely roleplay-focused, with excellent acting skills from all the players culminating in an hour-long, emotional conversation between the crew. Also, the ship finally gains a captain.

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