Exclusive interview with Readwise on the new Readwise to Obsidian plugin | LYT House Episode 4

Readwise’s new “Readwise to Obsidian” plugin is built to keep highlight notes continuously up to date inside Obsidian without destroying what users already wrote. The core promise is “append only” syncing: when new highlights arrive, the plugin adds them at the bottom of the relevant note rather than overwriting earlier content—an approach designed to protect the most valuable part of a knowledge workflow: personal connections, links, and annotations added after the initial import.

The integration starts with a one-time setup that connects Obsidian to Readwise, then runs a sync to export existing highlights. For heavy users, the export can take minutes—one example cited roughly 35,000–36,000 highlights—so the plugin includes manual sync controls and command-palette access (e.g., running sync from Obsidian’s command palette). After the initial import, the plugin’s behavior is what differentiates it from older “export once” approaches like markdown zip exports: it’s designed for ongoing reading, where new highlights keep coming in.

A major feature is customizable formatting via a templating engine (Jinja2). By default, the plugin can output highlights using simple structures, but power users can toggle on a full templating system to control the exported markdown, including YAML front matter, page metadata, highlight layout, and how highlight text becomes blocks in Obsidian. The plugin also generates “page metadata” fields such as author, full title (including subtitle handling), category (book/article/podcast/tweet), document tags, and the original URL—metadata that Readwise interprets from its library and lets users correct when classification is off (for example, PDFs sometimes being interpreted as articles).

The plugin’s “highlights header” and divider logic supports incremental updates. When users take more highlights later, the plugin appends a new timestamped section beneath the existing content, preserving any edits made above. That design directly targets a common fear in syncing workflows: resyncing shouldn’t erase the notes that were written in response to earlier highlights.

Beyond the export itself, Readwise positions the plugin as part of a broader product philosophy. Readwise’s central value proposition is not just syncing highlights into note apps; it’s the “Daily Review” habit that resurfaces highlights over time. To make that work, Readwise must store highlight data in its managed platform, which also shapes how the integration behaves.

The roadmap focuses on the most requested refinements from early public launch feedback. Top items include folder and file naming templating (including non-English preferences), mobile support with safeguards against duplication, additional template variables (such as highlight date handling), and the ability to filter what gets exported (e.g., only books or only tweets rather than exporting everything based on time). There’s also discussion of “bi-directional sync” as a longer-term goal—updating Readwise when users edit notes in Obsidian—though that depends on the technical constraints of note-taking ecosystems.

Overall, the plugin aims to make highlight-to-notes workflows dependable for power users who want control over formatting and metadata, while keeping the most fragile part of the system—user-authored meaning—safe from sync overwrites.