The dev behind the Obsidian TTRPG plugins // Jeremy Valentine

Obsidian plug-in developer Jeremy Valentine has built a suite of tools that turn tabletop role-playing sessions into something that can be planned, run, and managed entirely inside Obsidian—without bouncing between spreadsheets, websites, and separate apps. His most-used work centers on Dungeons & Dragons workflows: generating 5e-style stat blocks, rolling dice directly from those blocks, tracking initiative for multi-monster encounters, and organizing fantasy calendars and content schedules. The payoff is practical—faster prep, fewer context switches at the table, and a single “source of truth” vault for monsters, notes, and session logistics.

Valentine’s flagship plug-in for D&D-style monsters is a stat block generator that supports both SRD content and custom monsters, with flexible layouts that can be exported and shared. A key evolution is dice integration: stat blocks aren’t just formatted text anymore, they can trigger dice rolls from within the block itself, making combat math and checks feel native to the note-taking workflow. He also emphasizes that the layouts are designed to be forgiving—fields can be optional, and users can override or extend what renders based on what’s available in their bestiary.

For running encounters, Valentine highlights an initiative tracker that goes beyond basic turn order. It can handle groups of combatants, roll multiple monsters per group, and incorporate damage, healing, and statuses. He also added support for custom entries—useful for table-specific mechanics like “booming blade”—so the tracker can reflect the exact rules and homebrew needs of a campaign rather than forcing players into a generic template.

On the organization side, Fantasy Calendar is presented as both a game tool and a general planning system. While it’s built to model fantasy worlds (with constraints that make syncing to real-world calendars tricky), Valentine uses it to manage real content calendars too—dragging between compact and expanded views and tracking ongoing work in a single interface. He also uses Dice Roller in creative ways beyond combat: rolling on item tables by rarity, nesting rolls to automate multi-step generation, and using it to produce writing prompts that help break out of narrative ruts.

Several “non-TTRPG” plug-ins show how Valentine thinks about productivity inside Obsidian. Leaflet adds zoomable, clickable maps—useful for both game locations and real-world planning like researching a move to Portugal. Second Window (formerly Image Window) creates a separate Obsidian window for images or read-only note rendering, addressing the common multi-monitor problem in Electron-based apps. Markdown Attributes enables more targeted CSS theming by attaching HTML attributes to specific elements, and Obsidian Setting Search adds a quick search box that can jump directly to settings and even search across plug-ins.

The conversation also sheds light on how plug-ins become “official” in Obsidian’s community catalog: developers submit pull requests to the community plugins repository, then Obsidian’s maintainer and reviewers audit code for stability and security risks before approval. Valentine’s broader message is that the ecosystem is approachable—Obsidian’s TypeScript-based API is structured enough that many people build their first plug-in—and that support often happens through Discord and GitHub issues rather than paid work. His tools matter because they compress the gap between note-taking and running a game, letting campaigns live where the knowledge already is: in the vault.