diff --git a/.jules/showcase.md b/.jules/showcase.md
index 4ead3eb5..022ca06a 100644
--- a/.jules/showcase.md
+++ b/.jules/showcase.md
@@ -5,4 +5,5 @@
 *   **Missing Contributing Guide:** [RESOLVED] Users looking to contribute have no clear entry point. `CONTRIBUTING.md` has been enhanced with project structure and testing details.
 *   **Deployment Info Clutter:** Deployment instructions were mixed with local run instructions, making the "Quick Start" hard to find. These have been moved to `docs/DEPLOYMENT.md`.
 *   **Misleading Quick Start:** The `npm run dev` command implied it started the full stack, but the worker required a separate process. This led to "PENDING" simulation states for new users.
+*   **Unorganized Documentation Map:** [RESOLVED] The README's documentation map was a flat list of 12 unorganized links, causing navigation friction. Categorized into Core, Operations, and Worker setup to improve discovery.
 
diff --git a/README.md b/README.md
index 144ee622..7b6ea05e 100644
--- a/README.md
+++ b/README.md
@@ -47,19 +47,29 @@ cd worker_flutter && flutter run -d macos    # or: -d windows
 
 ## Documentation Map
 
+**Core Architecture & API**
 *   [Architecture Overview](docs/ARCHITECTURE.md)
-*   [Architecture Issues](docs/ARCHITECTURE_ISSUES.md)
 *   [API Reference](API.md)
 *   [Data Flow](DATA_FLOW.md)
+
+**Deployment & Operations**
 *   [Deployment Guide](docs/DEPLOYMENT.md)
-*   [Implementation Plan](docs/IMPLEMENTATION_PLAN_WORKER_SPLIT.md)
 *   [Mode Setup](docs/MODE_SETUP.md)
-*   [Precon Sync](docs/PRECON_SYNC.md)
 *   [Secrets Setup](docs/SECRETS_SETUP.md)
+*   [Precon Sync](docs/PRECON_SYNC.md)
 *   [Stale Sweeper](docs/STALE_SWEEPER.md)
 *   [Sweeper Alerting](docs/SWEEPER_ALERTING.md)
 *   [Sweeper Alert Policy](docs/sweeper-alert-policy.yaml)
 
+**Desktop Worker (Flutter)**
+*   [Auth Setup](worker_flutter/docs/AUTH_SETUP.md)
+*   [App Check Setup](worker_flutter/docs/APP_CHECK_SETUP.md)
+*   [Sentry Setup](worker_flutter/docs/sentry-setup.md)
+
+**Legacy / Planning**
+*   [Architecture Issues](docs/ARCHITECTURE_ISSUES.md)
+*   [Implementation Plan](docs/IMPLEMENTATION_PLAN_WORKER_SPLIT.md)
+
 ## Contributing
 
 We welcome contributions! Please see our [Contributing Guide](CONTRIBUTING.md) to get started.