diff --git a/.roo/rules-architect/AGENTS.md b/.roo/rules-architect/AGENTS.md
index e17aa06e25..0bfd625eaa 100644
--- a/.roo/rules-architect/AGENTS.md
+++ b/.roo/rules-architect/AGENTS.md
@@ -1,10 +1,7 @@
-# Architect Mode Rules
+# Project Architecture Rules (Non-Obvious Only)
 
-## Non-Obvious Architecture Constraints
-
-- Providers MUST be stateless - hidden caching layer assumes this
-- Webview and extension communicate through specific IPC channel patterns only
-- React hooks required because external state libraries break webview isolation
-- Large JSON operations must use `safeWriteJson()` for streaming (prevents memory issues)
-- TypeScript `noUncheckedIndexedAccess: true` - array/object access may return undefined
-- Import paths in packages/ require `.js` extensions despite TypeScript source
+- Webview and extension communicate ONLY through `src/core/webview/webviewMessageHandler.ts` patterns
+- React hooks required in webview - external state libraries break VSCode webview isolation
+- Monorepo has circular dependency on types package (intentional design)
+- `safeWriteJson()` mandatory for JSON writes - uses atomic writes with file locking
+- Database operations require specific directory: must `cd packages/evals` before running migrations
diff --git a/.roo/rules-ask/AGENTS.md b/.roo/rules-ask/AGENTS.md
index 38b89b6f3a..1c35929def 100644
--- a/.roo/rules-ask/AGENTS.md
+++ b/.roo/rules-ask/AGENTS.md
@@ -1,8 +1,7 @@
-# Ask Mode Rules
+# Project Documentation Rules (Non-Obvious Only)
 
-## Non-Obvious Documentation Context
-
-- `src/` contains VSCode extension code, NOT generic source (counterintuitive naming)
-- Two separate i18n systems: root `locales/` for extension, `webview-ui/src/i18n/` for UI
-- Provider examples in `src/api/providers/` are canonical reference (docs may be outdated)
-- Webview runs in VSCode context with restrictions (no localStorage, limited browser APIs)
+- `src/` contains VSCode extension code, NOT general source (counterintuitive naming)
+- `webview-ui/` is React UI in VSCode webview with severe restrictions (no localStorage, limited APIs)
+- Two separate i18n systems: `locales/` for extension, `webview-ui/src/i18n/` for UI
+- Monorepo workspace roots are `"src"` and `"webview-ui"` (not standard `packages/` structure)
+- Extension bundled with custom `esbuild.mjs`, webview uses Vite
diff --git a/.roo/rules-code/AGENTS.md b/.roo/rules-code/AGENTS.md
index 080bac7be0..686588167d 100644
--- a/.roo/rules-code/AGENTS.md
+++ b/.roo/rules-code/AGENTS.md
@@ -1,10 +1,8 @@
-# Code Mode Rules
+# Project Coding Rules (Non-Obvious Only)
 
-## Critical Non-Obvious Patterns
-
-- **MANDATORY**: Use `safeWriteJson()` from `src/utils/safeWriteJson.ts` for ALL JSON writes (prevents corruption via atomic writes with locking)
-- Tests MUST run from workspace directory: `cd src && npx vitest run` (NOT from root)
-- VSCode CSS variables must be added to `webview-ui/src/index.css` before use
-- State management via React hooks only (external state libraries break webview isolation)
-- Providers MUST be stateless (hidden caching layer assumes this)
-- Import paths in packages/ require `.js` extensions despite TypeScript source
+- Always use `safeWriteJson()` from `src/utils/safeWriteJson.ts` instead of `JSON.stringify` for file writes (prevents corruption)
+- Extension code in `src/` directory, NOT in `apps/` (counterintuitive structure)
+- Webview UI in `webview-ui/` runs with restricted APIs - no localStorage, limited browser features
+- IPC patterns MUST follow `src/core/webview/webviewMessageHandler.ts` structure
+- Tests must be in `__tests__` folders or `.spec.ts` files (vitest won't find them otherwise)
+- VSCode API mocked differently: `src/__mocks__/vscode.js` vs `webview-ui/src/__mocks__/vscode.ts`
diff --git a/.roo/rules-debug/AGENTS.md b/.roo/rules-debug/AGENTS.md
index ba25e01efc..fa068f6ca6 100644
--- a/.roo/rules-debug/AGENTS.md
+++ b/.roo/rules-debug/AGENTS.md
@@ -1,13 +1,7 @@
-# Debug Mode Rules
+# Project Debug Rules (Non-Obvious Only)
 
-## Non-Obvious Debug Access
-
-- Webview DevTools: Command Palette → "Developer: Open Webview Developer Tools" (NOT F12)
-- Extension logs: VSCode Output panel → "Roo Code" channel
-- Extension Host output channel shows different logs than Debug Console
-
-## Critical Debug Patterns
-
-- IPC messages fail silently without try/catch in `packages/ipc/src/`
-- Tests MUST run from workspace directory: `cd src && npx vitest run`
-- Webview runs in restricted context (no localStorage, limited browser APIs)
+- Extension logs only visible in "Extension Host" output channel, NOT Debug Console
+- Webview dev tools accessed via Command Palette > "Developer: Open Webview Developer Tools" (not F12)
+- Database migrations MUST run from `packages/evals/` directory: `cd packages/evals && pnpm db:migrate`
+- IPC messages fail silently if not wrapped in try/catch in webview message handlers
+- Two separate mock systems: `src/__mocks__/vscode.js` for extension, `webview-ui/src/__mocks__/vscode.ts` for UI
diff --git a/AGENTS.md b/AGENTS.md
index e575973371..cd0c0c31b2 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -2,20 +2,36 @@
 
 This file provides guidance to agents when working with code in this repository.
 
-## Critical Non-Obvious Patterns
+## Critical Non-Obvious Rules
 
-- **JSON Writes**: MUST use `safeWriteJson()` from `src/utils/safeWriteJson.ts` for ALL JSON writes (atomic writes with locking, handles streaming)
-- **Test Execution**: Tests MUST run from workspace directory: `cd src && npx vitest run` or `cd webview-ui && npx vitest run` (NOT from root)
-- **Import Extensions**: Use `.js` extensions in packages/ imports despite TypeScript source files
-- **Bootstrap**: `pnpm install` auto-bootstraps via `scripts/bootstrap.mjs` if pnpm not found
-- **Webview DevTools**: Access via Command Palette → "Developer: Open Webview Developer Tools" (not F12)
-- **VSCode CSS Variables**: Must be added to `webview-ui/src/index.css` before use in components
-- **React Hooks Required**: External state libraries break webview isolation - use React hooks only
-- **noUncheckedIndexedAccess**: TypeScript strict mode with this enabled - array/object access may return undefined
+- **MUST** use `safeWriteJson()` from `src/utils/safeWriteJson.ts` for ALL JSON file writes (prevents corruption via atomic writes with locking)
+- Test files exempt from safeWriteJson rule
 
-## Architecture Gotchas
+## Project Structure (Non-Standard)
 
-- `src/` contains VSCode extension backend (not generic source)
-- `webview-ui/` is React frontend in VSCode webview (restricted APIs, no localStorage)
-- IPC messages between extension/webview must use typed interfaces from `packages/types`
-- Provider implementations must be stateless (hidden caching layer assumes this)
+- `src/` contains VSCode extension code (NOT general source - counterintuitive naming)
+- `webview-ui/` is the React UI that runs in VSCode webview (separate from extension)
+- Two separate i18n systems: root `locales/` for extension, `webview-ui/src/i18n/` for UI
+- Monorepo uses pnpm workspaces with unusual paths: `"src"` and `"webview-ui"` as workspace roots
+
+## Testing Specifics
+
+- Tests MUST be in `__tests__` folders or `.spec.ts` files (vitest configured this way)
+- VSCode module mocked at `src/__mocks__/vscode.js` and `webview-ui/src/__mocks__/vscode.ts`
+- Run single test: `pnpm test -- path/to/test.spec.ts`
+
+## Build Commands (Directory-Sensitive)
+
+- Database operations MUST run from `packages/evals/` directory: `cd packages/evals && pnpm db:migrate`
+- Extension bundling uses custom `esbuild.mjs` script, not standard vite/webpack
+
+## Webview Restrictions
+
+- Webview has NO localStorage, limited browser APIs
+- IPC communication through specific patterns in `src/core/webview/webviewMessageHandler.ts`
+- State management requires React hooks only (external state libraries break isolation)
+
+## Code Style (Non-Standard)
+
+- Tabs not spaces (4-width), no semicolons, bracket same line
+- Line width 120 chars (not default 80)