Rolling with Difficulty Table
149 episodes listed below
Actual play, aftertalk, and tactical table chatter.
Rolling with Difficulty follows a D&D table through campaign aftermath, character progression, and audience questions around its Planescape stories. Recent episodes lean into Hunting Party Q&As, level-ups, tactical choices, party dynamics, and side conversations about systems like Draw Steel.
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Rolling with Difficulty sits at the intersection of actual-play fandom, campaign debrief, and tabletop craft talk. It is rooted in D&D and Planescape, but the recent material is less about polished narration than about hearing a table process what happened and what comes next. Hunting Party is the main focus. The campaign's Q&A episodes field audience questions about character choices, emotional fault lines, party splitting, dragons, NPCs, and fantasy travel. The conversations move quickly. A joke about chat can turn into a practical point about tension in combat, and a character aside can become a clearer read on how the party actually functions. The level-up episodes are especially mechanical. They walk through hit points, feats, spells, psionic powers, invocations, portent dice, and the immediate excitement of a character becoming more dangerous or more survivable. That crunch is part of the charm. The table sounds invested in both the math and the meaning, so a new power is treated as a tactical option and a character beat at the same time. Recent Q&As also pull back the curtain on recording pace, campaign structure, and how much the players know before listeners do. It feels live and lightly chaotic. The Draw Steel talkback adds a useful comparison point, as the players discuss cinematic combat, writer's-room coordination, action economy, and the difference between tactical planning and in-character roleplay. Rolling with Difficulty suits listeners who like actual play communities where the table itself is part of the entertainment. It rewards people who enjoy hearing campaign consequences discussed in plain terms. The show can be rules-heavy, but rarely cold. Its energy comes from players teasing each other, correcting themselves, and turning specific play moments into usable tabletop insight.
Made for: For D&D actual-play listeners who enjoy campaign Q&As, character mechanics, party dynamics, and table talk. It especially suits fans who like rules discussion alongside jokes and emotional character fallout.
What sets it apart: The show treats companion episodes as part of the experience, not filler. Level-ups, Q&As, and system talk become a way to understand how the campaign works at the table.
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...
Shrimp theology gives way to action economy, and somehow you're invested in both.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A focused Draw Steel talkback on writer's-room combat and the near-TPK that put it under pressure.
Draw Steel comes through as a useful test case for the space between a tactical turn and the story it leaves behind. Rolling With Difficulty brings in players Red and Noir to talk through MCDM's RPG, with the conversation returning to a productive tension: combat rewards…
A breezy season-two finale Q and A that turns table talk into a relaxed campaign wrap-up.
Hunting Party closes season two with a light Q and A that keeps the mood easy while the cast fields listener questions, takes a short pause, and then heads back to the beast lands.
A loose, funny Q&A that turns avoidance, secrets, and Kareek into real character insight.
Rolling with Difficulty uses its Q&A as a pressure release, and that gives the conversation a loose, lived in feel. The cast is open about avoidance, close calls with tragic backstories, and why Kareek lands as the season's heart.
A loose, lively season wrap that gets more specific, and funnier, the longer it goes.
A post-season Q&A turns Campaign 3's first full season into a loose, funny debrief built from chat questions, email questions, and plenty of Katya being Katya.
Lore-heavy campaigns, live-table chaos.
Table chaos, sharp play, bad plans.
Dry banter, bad odds, real dice.
Grim fantasy, bad plans, live-table chaos.
Rolling with Difficulty's mid-season Q&A for season four addresses Katya's unknown origins, including the claim that she never killed anyone as a werecat and instead misread her beast side as evil.
["Rolling with Difficulty's \"Draw Steel Talkback: Draw Steel\" treats MCDM's unreleased RPG as a patron reward and a direct comparison point for D&D.", "Red and Noir describe Draw Steel as a \"fantasy, heroic, tactical, cinematic\" game where level-one characters already act like established heroes.", "Noir focuses on the \"no whiff\" roll tiers, while Red explains tactician-triggered movement, shadow teleporting, and the corruption damage weakness on his build.", "The back half covers stamina, recoveries, zero-stamina play, squads, villain actions, negotiation scenes with interest and patience, and montage tasks that give noncombat scenes real structure."]
Rolling with Difficulty's "Hunting Party Q&A: Fresh Prey" is a season two finale Q&A that opens with the cast taking live questions from email and chat before a few months-long break from the Beast Lands.
This episode discusses the level 14 advancement of a Dungeons & Dragons party, focusing on character upgrades like hit point increases and new subclass features such as Psionic Evolution.
["Rolling with Difficulty's \"Hunting Party Q&A: On the Scent\" opens with Sophia saying the crew is \"farther ahead than we usually are\" and teasing \"an awful lot of secrets.\"", "Sophia, Austin, Red, Wally, and Noir answer questions about BeastLords, the ant queen, Garou and Katya's tension, and how the Beastlands campaign keeps branching after season one.", "Austin says the ant queen fight would have been smaller before her BeastLord transition, with fewer ants, fewer lieutenants, and no Abyssal lair yet.", "The episode also covers combat tuning, including why Austin avoids stun, incapacitated, and paralyzed, and how the table uses lines, veils, and post-session talks to keep the roleplay separate from the players."]
The hosts discuss their characters reaching level 13 in a Dungeons & Dragons campaign, covering hit point increases, proficiency bonuses, new spells, and ability score improvements.
Hunting Party Q&A: Picking Up the Trail opens with a spoiler warning for the entire previous season and a post-season check-in on Campaign 3.
This episode is a live Q&A session for the 'Hunting Party' podcast's third campaign, where hosts take questions from email and YouTube chat about the new campaign and other topics.
The hosts discuss leveling up their D&D characters to level 12, focusing on hit points, ability score improvements, and feat choices for their Sorcerer and Wizard characters.
This episode is a live Q&A session wrapping up a season, where the hosts and a guest answer fan questions from email and chat about the show's campaign and character lore.
The hosts discuss their characters reaching level 7 in a Dungeons & Dragons campaign, focusing on new spells like Polymorph and character stats.
The hosts announce that the current season of their detective podcast 'Open and Shut' will be the final one, with plans to conclude the story and launch a new Planescape campaign this summer.
A D&D actual play podcast where the characters level up and the DM discusses new abilities.
A D&D actual play podcast set in the Planescape, following adventurers on the Astral Sea and in Sigil.
The players level up their characters to level five mid-adventure, discussing class choices and ability score improvements.