From b6a0a57893d00657f9362a248fcadcf82af722c9 Mon Sep 17 00:00:00 2001
From: Andre Padez <andre.padez@gmail.com>
Date: Wed, 25 Feb 2026 16:04:11 +0000
Subject: [PATCH] thinking

---
 SECURITY_AUDIT.md                             | 593 ++++++++++++++++++
 src/servers/api/pi/pi-bridge.ts               |  10 +
 src/servers/api/pi/types.ts                   |   3 +
 src/servers/api/pi/websocket.ts               |   7 +-
 .../api/server-settings/sync-pi-config.ts     |  16 +-
 .../apps/Chat/ChatLauncher/ChatLauncher.tsx   |   2 +
 .../Chat/EmbeddableChat/useEmbeddableChat.ts  |   5 +
 .../src/apps/Chat/components/InputArea.tsx    |   4 +
 .../apps/Chat/components/ModelSelector.tsx    |  73 ++-
 .../components/TaskRunnerModal.tsx            |   2 +
 .../officerdev/src/hooks/usePiChat.ts         |   5 +
 11 files changed, 698 insertions(+), 22 deletions(-)
 create mode 100644 SECURITY_AUDIT.md

diff --git a/SECURITY_AUDIT.md b/SECURITY_AUDIT.md
new file mode 100644
index 00000000..9f9dee81
--- /dev/null
+++ b/SECURITY_AUDIT.md
@@ -0,0 +1,593 @@
+# Security Audit — Officer.dev Pi-Monorepo
+
+**Date:** 2026-02-25
+**Scope:** Full-stack audit of server, frontend, and infrastructure code.
+
+---
+
+## Executive Summary
+
+The codebase has solid foundations (JWT + argon2 auth, WebAuthn passkeys, token blacklisting, Docker-sandboxed terminals, role-based access control). However, several critical and high-severity vulnerabilities exist — primarily around CORS misconfiguration, weak secret management, unauthenticated admin routes, XSS via `rehype-raw`, and token exposure in URLs.
+
+**Totals:** 5 Critical, 13 High, 14 Medium, 9 Low, 5 Info
+
+---
+
+## CRITICAL
+
+### C1. Weak JWT Secret — `"officer"`
+
+**Files:** `.env` (line 2), `src/servers/jwt.ts` (lines 2, 25)
+
+The live `.env` contains `JWT_SECRET="officer"` — a single dictionary word. The `.env.example` uses `"change-me"`. The server uses a non-null assertion (`JWT_SECRET!`) with no startup validation for length or complexity.
+
+**Impact:** Complete authentication bypass. Anyone who knows/guesses the secret can forge JWTs for any user including Super Admin.
+
+**Remediation:**
+- Generate a cryptographically random secret: `openssl rand -base64 32`
+- Add a startup guard: throw if `JWT_SECRET` is absent or shorter than 32 characters
+- Update `.env.example` with a placeholder: `JWT_SECRET=<generate with: openssl rand -base64 32>`
+
+---
+
+### C2. Global CORS Wildcard on All API Routes
+
+**File:** `src/servers/hono.ts` (lines 36–42)
+
+```ts
+cors({ origin: '*', allowHeaders: ['Content-Type', 'Authorization'] })
+```
+
+Applied to every route. The `Authorization` header allowlist means any website can make cross-origin requests using a victim's token (obtained via XSS or other leaks).
+
+**Impact:** Full cross-origin request forgery against all API endpoints for users tricked into visiting a malicious page.
+
+**Remediation:** Replace `origin: '*'` with the allowlist from `origin-validation.ts` (`ALLOWED_ORIGINS`). Use a dynamic origin validation function in the CORS middleware.
+
+---
+
+### C3. Server-Settings Routes Entirely Unauthenticated
+
+**Files:** `src/servers/hono.ts` (lines 46–48), `src/servers/api/server-settings/server-settings.ts`
+
+The `serverSettingsRouter` is mounted on the **public** router (outside `protectedRouter`). All sub-routes — SMTP, TTS, STT, OCR, SearXNG, Pi-Mono, Claude Code, OpenCode, applications, resources — have no auth checks. Any unauthenticated request can read settings (including masked credentials), write new settings, and trigger software installs.
+
+**Impact:** Full server configuration takeover by any unauthenticated user.
+
+**Remediation:** Move `serverSettingsRouter` inside `protectedRouter`. Add Super Admin role checks on all write operations. Exempt only `GET /api/server-settings/onboarding-complete` as public.
+
+---
+
+### C4. Unauthenticated Dev-Server WebSocket Proxy
+
+**Files:** `src/server.tsx` (lines 114–139), `src/servers/api/dev-server/router.ts` (lines 241–268), `src/servers/hono.ts` (line 49)
+
+The dev-server proxy (`/api/dev-server-proxy/*`) is mounted on the public router. WebSocket upgrades carry no authentication. The HTTP proxy has no auth gate either. Additionally, the Referer header fallback allows probing any running dev server.
+
+**Impact:** Unauthenticated access to dev-servers spawned for any user, which may expose internal APIs, HMR endpoints, or local services.
+
+**Remediation:** Require a valid JWT (via query param) before upgrading WebSocket connections. Apply `userMiddleware` to the HTTP proxy router.
+
+---
+
+### C5. AI Chat Messages Rendered with `rehype-raw` — LLM-Driven XSS
+
+**File:** `src/workspaces/officerdev/src/apps/Chat/components/MessageBubble.tsx` (lines 132, 181)
+
+```tsx
+<ReactMarkdown rehypePlugins={[rehypeRaw]}>{assistantText}</ReactMarkdown>
+```
+
+AI-generated assistant responses containing HTML tags (`<script>`, `<iframe>`, `<img onerror=...>`) are rendered verbatim into the DOM.
+
+**Impact:** Stored XSS in the chat interface. Prompt injection via uploaded files, tool results, or a compromised AI provider can execute arbitrary JavaScript — exfiltrating the Bearer token from localStorage.
+
+**Remediation:** Remove `rehype-raw` from chat rendering. If basic HTML is needed, use `rehype-sanitize` with an allowlist of safe tags (no `<script>`, `<iframe>`, event handlers).
+
+---
+
+## HIGH
+
+### H1. Bearer Token Stored in `localStorage`
+
+**Files:** `src/workspaces/hooks/src/useAuth/useAuth.ts` (lines 56, 84, 99), `usePasskeys.ts` (line 44)
+
+The primary 30-day authentication token is stored in `localStorage`, readable by any JavaScript on the page origin — including via XSS.
+
+**Impact:** Combined with any XSS vector (C5, H5, H6), an attacker can exfiltrate the token and hijack the session.
+
+**Remediation:** Use `HttpOnly` cookies for the Bearer token so it is inaccessible to JavaScript.
+
+---
+
+### H2. Bearer Token Exposed in WebSocket/Media URL Query Strings
+
+**Files:** `src/workspaces/officerdev/src/hooks/usePiChat.ts` (line 58), `src/workspaces/officerdev/src/apps/Terminal/Terminal.tsx` (line 43), `src/workspaces/officerdev/src/apps/FileViewer/file-types.ts` (lines 144–148), `src/server.tsx` (line 87), `src/servers/_middlewares/user-middleware.ts` (line 32)
+
+The full 30-day JWT appears in URLs for WebSocket connections, raw file downloads, and media transcoding.
+
+**Impact:** Tokens are logged by servers, proxies, CDNs; stored in browser history; sent in `Referer` headers; visible to browser extensions and analytics scripts.
+
+**Remediation:** For WebSocket: send the token as the first message after connection. For media: use short-lived single-use tokens generated by a dedicated endpoint (e.g., 60-second TTL).
+
+---
+
+### H3. `rehype-raw` Used in Multiple Content-Rendering Contexts
+
+**Files:**
+- `src/apps/officer-web/Screens/Dashboard/CapabilityPage.tsx` (line 354)
+- `src/apps/officer-web/Screens/Dashboard/Plans/index.tsx` (line 5)
+- `src/apps/officer-web/Screens/Dashboard/Automation/CapabilityDetailView.tsx` (line 5)
+- `src/apps/officer-web/Screens/Dashboard/Settings/ResourceSettings/Resources.tsx` (line 5)
+- `src/workspaces/components/MarkdownEditor.tsx` (line 98)
+- `src/workspaces/officerdev/src/apps/FileViewer/renderers/MarkdownRenderer.tsx` (line 43)
+
+Markdown from user-editable files (skills, tasks, processes, arbitrary filesystem files) is rendered with `rehype-raw`, allowing embedded HTML/script injection.
+
+**Impact:** Stored XSS. A malicious Markdown file opened in the file viewer or capability page executes arbitrary JavaScript.
+
+**Remediation:** Add `rehype-sanitize` alongside `rehype-raw` in all locations, or remove `rehype-raw` entirely for untrusted content.
+
+---
+
+### H4. Email HTML Rendered with `allow-same-origin` Sandbox
+
+**File:** `src/apps/officer-web/Screens/Dashboard/Email/EmailReader.tsx` (lines 25–41)
+
+HTML email bodies are written into an iframe via `document.write()` with `sandbox="allow-same-origin"`. While `allow-scripts` is not set (blocking script execution), CSS injection and phishing forms can still render.
+
+**Impact:** Email phishing attacks rendered within the Officer UI. CSS-based data exfiltration possible.
+
+**Remediation:** Change to `sandbox=""` (no attributes). Consider running email HTML through DOMPurify server-side.
+
+---
+
+### H5. Mass Email Template — Unsanitized `dangerouslySetInnerHTML`
+
+**Files:** `src/workspaces/emailer/emails/MassEmail.tsx` (line 23), `src/workspaces/components/MarkdownEditor.tsx` (line 41)
+
+```tsx
+<div dangerouslySetInnerHTML={{ __html: greetingHtml + content }} />
+```
+
+User names are interpolated via `String.replace()` without HTML encoding. A user with `<script>` in their name triggers XSS in the admin's email preview.
+
+**Impact:** Stored XSS in admin email previews.
+
+**Remediation:** HTML-encode all interpolated user data. Use DOMPurify on the final output.
+
+---
+
+### H6. `applyGlobals` — Arbitrary JavaScript Injection
+
+**File:** `src/workspaces/injector/apply-changes/apply-globals.ts` (lines 11–13)
+
+```ts
+script.innerHTML = `;(function(){${globalJavascript}})();`;
+document.body.appendChild(script);
+```
+
+A/B test experiment configuration injects arbitrary JavaScript into every user's browser session.
+
+**Impact:** If a non-admin can influence the `globalJavascript` payload, it's instant code execution across the organization.
+
+**Remediation:** Restrict write access to experiment configurations to Admin/Owner/Super Admin. Audit API endpoints that set `globalJavascript`.
+
+---
+
+### H7. Unsanitized URL Passed to `yt-dlp` and `git clone`
+
+**File:** `src/servers/api/file-browser/router.ts` (lines 901–944)
+
+Both `yt-dlp` and `git clone` are invoked with user-supplied URLs without scheme validation. `git clone file:///etc/passwd` reads local files. `yt-dlp` accepts plugin URLs and SSRF targets.
+
+**Impact:** Local file exfiltration via `file://`, SSRF to internal services, potential exploitation via git remote helpers.
+
+**Remediation:** Validate URLs to allow only `http://` and `https://` schemes. Add `--` argument terminator and `--no-config` for yt-dlp. Add `--no-local` for git.
+
+---
+
+### H8. File Browser Exposes Host Filesystem to Super Admin
+
+**File:** `src/servers/api/file-browser/router.ts` (lines 54–61)
+
+Super Admin can access `~` (host homedir) and `officer.dev` (project root), giving read/write access to `.env`, auth store files, API keys, and the entire host filesystem.
+
+**Impact:** A compromised Super Admin account (or forged JWT — trivial with C1) has full host filesystem access.
+
+**Remediation:** Restrict roots to `DATA_PATH` only. Remove `~` and `officer.dev` roots or restrict them to read-only with path filtering.
+
+---
+
+### H9. Rate Limiting Disabled Outside Production
+
+**File:** `src/servers/_middlewares/rate-limiter.ts` (lines 27–28, 45–46)
+
+All rate limiters are bypassed unless `PUBLIC_BUILD_ENV` is `production` or `staging`. The `.env` doesn't set this variable, so rate limiting is off by default.
+
+**Impact:** Unrestricted brute-force attacks on passwords, verification codes, and passkey challenges in any deployment that doesn't explicitly set `PUBLIC_BUILD_ENV=production`.
+
+**Remediation:** Enable rate limiting by default. Only disable when `PUBLIC_BUILD_ENV === 'test'`.
+
+---
+
+### H10. Rate Limiter Uses Spoofable `X-Forwarded-For`
+
+**File:** `src/servers/_middlewares/rate-limiter.ts` (line 34)
+
+The default key is the raw `X-Forwarded-For` header, which is client-controlled and trivially spoofed.
+
+**Impact:** Complete rate limit bypass by setting any `X-Forwarded-For` value.
+
+**Remediation:** Use the actual socket IP (Bun provides this) or validate `X-Forwarded-For` against a trusted proxy list.
+
+---
+
+### H11. Terminal Sidecar Users Get Passwordless Sudo
+
+**File:** `src/servers/api/terminal/entrypoint.sh` (line 24)
+
+```sh
+echo "$USERNAME ALL=(ALL) NOPASSWD:ALL" > /etc/sudoers.d/terminal-user
+```
+
+**Impact:** Full root inside container. If Docker sandboxing is bypassed or misconfigured, this escalates to host root.
+
+**Remediation:** Remove NOPASSWD sudo entirely or restrict to specific commands.
+
+---
+
+### H12. Google OAuth State Parameter Not Signed
+
+**File:** `src/servers/api/integrations/integrations.ts` (lines 134–150)
+
+The OAuth state is just `base64(JSON)` — no HMAC. The `origin` query parameter is user-controlled and embedded in the state. The callback is a public endpoint.
+
+**Impact:** OAuth CSRF. An attacker can craft a state parameter to bind their Google account to a victim's email.
+
+**Remediation:** Sign the state with HMAC using `JWT_SECRET`. Derive `redirectUri` from `PUBLIC_URL`, not from the query parameter.
+
+---
+
+### H13. `maxRequestBodySize` Set to 50 GB
+
+**File:** `src/server.tsx` (line 144)
+
+**Impact:** DoS by exhausting server memory/disk with a single request.
+
+**Remediation:** Set a reasonable limit (100 MB–1 GB). Apply per-route size limits for file uploads.
+
+---
+
+## MEDIUM
+
+### M1. Rate Limiter Only Counts Failed Requests
+
+**File:** `src/servers/_middlewares/rate-limiter.ts` (lines 59–67)
+
+Only 4xx responses increment the counter. Successful auths reset the window.
+
+**Impact:** Attackers can interleave successful/failed attempts to effectively bypass rate limits.
+
+**Remediation:** Count all requests toward the limit, regardless of response code.
+
+---
+
+### M2. Password Reset Tokens Not Blacklisted After Use
+
+**File:** `src/servers/api/auth/reset-password.ts`
+
+The same reset link can be used multiple times within its validity window.
+
+**Impact:** Reset link replay — an intercepted link works even after the user has already reset their password.
+
+**Remediation:** Blacklist the token's JTI immediately after first use.
+
+---
+
+### M3. Password Validation Skipped in Non-Production
+
+**File:** `src/servers/api/auth/change-password.ts` (lines 8–13)
+
+```ts
+if (isProduction) validatePassword(newPassword);
+```
+
+**Impact:** Weak/empty passwords accepted if `PUBLIC_BUILD_ENV` is unset in production.
+
+**Remediation:** Always validate password complexity regardless of environment.
+
+---
+
+### M4. User Settings PUT — No Schema Validation or Size Limit
+
+**File:** `src/servers/api/settings/settings.ts` (lines 43–51)
+
+The entire request body is written verbatim to the settings JSON file.
+
+**Impact:** Disk exhaustion, injection of arbitrary keys that may affect server-side logic (e.g., `tts.voice`).
+
+**Remediation:** Apply a size limit (64 KB) and schema validation for known fields only.
+
+---
+
+### M5. SSRF via Scrape Endpoint (Playwright)
+
+**File:** `src/servers/api/scrape/scrape.ts` (lines 31–45)
+
+The scrape endpoint navigates Playwright to any user-supplied URL without validation.
+
+**Impact:** SSRF to internal network, cloud metadata (`169.254.169.254`), and localhost services. Full HTML returned.
+
+**Remediation:** Validate scheme (`http://`/`https://` only), resolve hostname, block private IP ranges.
+
+---
+
+### M6. SSRF via User-Configured OCR/TTS/STT URLs
+
+**File:** `src/servers/api/file-browser/router.ts` (lines 509–545)
+
+External API URLs come from server configuration (writable via unauthenticated C3 routes). An attacker can point them to internal services.
+
+**Impact:** SSRF to internal network via AI provider proxy.
+
+**Remediation:** Fix C3 first. Then validate configured URLs don't resolve to private/loopback ranges.
+
+---
+
+### M7. OCR Sends Arbitrary Files to External Vision API
+
+**File:** `src/servers/api/file-browser/router.ts` (lines 481–555)
+
+MIME type derived from extension only. No file type validation or size limit.
+
+**Impact:** Data exfiltration of non-image files (config, keys) to third-party AI providers.
+
+**Remediation:** Validate magic bytes, enforce max size, restrict allowed extensions.
+
+---
+
+### M8. `resend-verification` Leaks User Existence
+
+**File:** `src/servers/api/auth/resend-verification.ts` (line 13)
+
+Returns distinct responses for "user not found" vs "already verified" with no rate limiting.
+
+**Impact:** Automated user enumeration.
+
+**Remediation:** Return the same success response regardless. Add rate limiting.
+
+---
+
+### M9. API Keys + `JWT_SECRET` Leaked to AI Subprocess
+
+**File:** `src/servers/api/pi/pi-bridge.ts` (lines 234–235, 281–283)
+
+The unsandboxed path spreads `process.env` (including `JWT_SECRET`, DB credentials, SMTP passwords) into every Pi process.
+
+**Impact:** A prompt-injected AI model can exfiltrate all server secrets.
+
+**Remediation:** Explicitly enumerate allowed environment variables. Never pass `JWT_SECRET` or DB credentials to AI subprocesses.
+
+---
+
+### M10. Auth Store Has No File Locking
+
+**File:** `src/databases/officer_db/src/store.ts`
+
+In-memory arrays with async file writes. No mutex or write queue.
+
+**Impact:** Concurrent writes (signups, signouts) can lose data or corrupt the JSON file.
+
+**Remediation:** Add a write lock/queue. Consider SQLite for the auth store.
+
+---
+
+### M11. JSON Parse Errors Silently Swallowed in Body Parser
+
+**File:** `src/servers/_middlewares/body-parser.ts` (lines 27–29)
+
+```ts
+} catch (ex) {
+  // throw errors.BAD_REQUEST('Invalid request body');
+}
+```
+
+**Impact:** Malformed request bodies become `{}`, bypassing input validation in handlers that don't check required fields.
+
+**Remediation:** Uncomment the `throw errors.BAD_REQUEST(...)` line.
+
+---
+
+### M12. Module-Level Token Singleton Race Condition
+
+**File:** `src/workspaces/hooks/src/useClient.ts` (lines 2–14)
+
+`theToken` is a module-level variable set once per `createClient()` call. Stale after logout.
+
+**Impact:** Authenticated requests may continue after logout in race conditions.
+
+**Remediation:** Read the token fresh from storage in `getHeaders()` rather than caching in a module variable.
+
+---
+
+### M13. No Content Security Policy
+
+**Files:** `src/apps/officer-web/index.html`, `src/servers/hono.ts`
+
+No CSP header or meta tag. Every XSS vulnerability has maximum impact.
+
+**Impact:** No defense-in-depth against script injection.
+
+**Remediation:** Add a CSP header at the server level. At minimum: `default-src 'self'; script-src 'self'; object-src 'none'; base-uri 'self'`.
+
+---
+
+### M14. Gmail Token Cache Is Global, Not Per-User
+
+**File:** `src/servers/queue/handlers/gmail-sync.ts` (lines 40–46)
+
+Module-level `cachedAccessToken` shared across all users.
+
+**Impact:** One user's Gmail access token may be used for another user's API calls.
+
+**Remediation:** Scope the cache by user email using a `Map`.
+
+---
+
+## LOW
+
+### L1. `TEST_USERS` Backdoor Mechanism in Signin
+
+**File:** `src/servers/api/auth/signin.ts` (lines 11, 23, 33)
+
+Currently empty, but the code allows bypassing password and passkey verification for listed user IDs.
+
+**Remediation:** Remove the mechanism entirely.
+
+---
+
+### L2. API Keys and OAuth Tokens Stored Unencrypted at Rest
+
+**Files:** `src/servers/api/server-settings/pi-mono.ts` (line 10), `src/databases/officer_db/src/store.ts`
+
+All provider API keys, Google OAuth tokens, and passkey data stored as plaintext JSON.
+
+**Remediation:** Encrypt sensitive values at rest using a key derived from a separate `ENCRYPTION_KEY` env variable.
+
+---
+
+### L3. Sensitive Credentials Returned to Frontend Unnecessarily
+
+**Files:** `src/apps/officer-web/Screens/Dashboard/Settings/IntegrationsSettings/GoogleOAuthConfig.tsx` (line 201), `SMTPSection.tsx`
+
+Google OAuth `clientSecret` and SMTP passwords are fetched to frontend state on every settings page load.
+
+**Remediation:** Return masked values for display. Only require the full value when updating.
+
+---
+
+### L4. Host `$HOME` Path Leaked in API Response
+
+**File:** `src/servers/api/pi/rest.ts` (line 34)
+
+```ts
+return ctx.json({ models, providerNames, hostHome: process.env.HOME ?? '' });
+```
+
+**Remediation:** Remove `hostHome` from the response or restrict to Super Admin.
+
+---
+
+### L5. Verification Codes Not Cleared from URL
+
+**Files:** `src/apps/officer-web/Screens/Authentication/Verify.tsx` (line 19), `useResetPassword.ts` (line 14)
+
+Codes remain in browser history and `Referer` headers.
+
+**Remediation:** Call `history.replaceState(null, '', window.location.pathname)` after reading the code.
+
+---
+
+### L6. Missing HTTP Security Headers
+
+No `X-Content-Type-Options`, `X-Frame-Options`, `Referrer-Policy`, `Permissions-Policy`, or `Strict-Transport-Security` headers.
+
+**Remediation:** Add a security headers middleware to `hono.ts`.
+
+---
+
+### L7. Package Install Endpoints Lack Role Restriction
+
+**Files:** `src/servers/api/server-settings/claude-code.ts` (line 24), `opencode.ts` (line 47), `pi-mono.ts` (line 275)
+
+Three endpoints run `curl | bash` or `npm install -g` on the host. Even after fixing C3, any authenticated user (not just Super Admin) can trigger installs.
+
+**Remediation:** Restrict to Super Admin. Add integrity checks (SHA256 pinning).
+
+---
+
+### L8. Token Accepted via URL `officerToken` Parameter
+
+**File:** `src/workspaces/hooks/src/useAuth/useAuth.ts` (line 27)
+
+Token in URL is stored permanently in browser history and sent in `Referer` headers. Not cleared from the URL after consumption.
+
+**Remediation:** Use short-lived single-use tokens for embedding. Call `history.replaceState` to remove from URL bar.
+
+---
+
+### L9. Bootstrap Race Condition
+
+**File:** `src/servers/api/auth/auth.ts` (lines 35–36)
+
+Two concurrent bootstrap requests could create two Super Admins before `getUserCount()` reflects the first.
+
+**Remediation:** Add a mutex or atomic check-and-insert.
+
+---
+
+## INFO
+
+### I1. No Automated Security Test Coverage
+
+No tests exist for auth flows, authorization, rate limiting, or path traversal guards.
+
+### I2. Stack Traces Logged to Console
+
+**File:** `src/servers/hono.ts` (lines 89–90) — full stack traces logged. If logs are user-accessible, this reveals internal paths.
+
+### I3. `passwordChangedAt` Not Checked in WebSocket Upgrade
+
+**File:** `src/server.tsx` (lines 86–112) — existing WebSocket connections are not invalidated after password change.
+
+### I4. Docker Container Map File Has No Integrity Protection
+
+**File:** `src/servers/api/terminal/websocket.ts` (line 30) — plain JSON at a known path, tamperable to redirect terminal sessions.
+
+### I5. `preinstall` Script Rejects Non-Node 22 but Project Uses Bun
+
+**File:** `package.json` (line 11) — inconsistent runtime enforcement.
+
+---
+
+## Prioritized Remediation Plan
+
+### Immediate (do first)
+
+1. **Rotate JWT secret** (C1) — generate a 256-bit random value, add startup length check
+2. **Fix CORS** (C2) — replace `origin: '*'` with `ALLOWED_ORIGINS` allowlist
+3. **Protect server-settings routes** (C3) — move inside `protectedRouter` + Super Admin role check
+4. **Protect dev-server proxy** (C4) — require JWT for WebSocket upgrades and HTTP proxy
+5. **Remove `rehype-raw` from chat** (C5) — or add `rehype-sanitize` with strict allowlist
+
+### Short-term (next sprint)
+
+6. **Move token to `HttpOnly` cookies** (H1, H2) — eliminates XSS token theft and URL leakage
+7. **Add `rehype-sanitize` everywhere** (H3) — all Markdown rendering of user content
+8. **Validate URLs for git-clone/yt-dlp/scrape** (H7, M5) — allow only `http://`/`https://`
+9. **Enable rate limiting by default** (H9) — disable only in `test` environment
+10. **Fix rate limiter key** (H10) — use socket IP, not `X-Forwarded-For`
+11. **Sign OAuth state** (H12) — HMAC with `JWT_SECRET`
+12. **Reduce `maxRequestBodySize`** (H13) — 100 MB or less
+13. **Uncomment body parser error** (M11) — fail loudly on malformed JSON
+
+### Medium-term
+
+14. **Add Content Security Policy** (M13)
+15. **Add HTTP security headers** (L6)
+16. **Blacklist password reset tokens after use** (M2)
+17. **Always validate password complexity** (M3)
+18. **Scope Gmail token cache per user** (M14)
+19. **Restrict file browser roots** (H8) — remove `~` and `officer.dev` access
+20. **Filter AI subprocess environment** (M9) — never pass `JWT_SECRET` or DB credentials
+21. **Add schema validation to settings PUT** (M4)
+22. **Restrict install endpoints to Super Admin** (L7)
+
+### Longer-term
+
+23. Encrypt sensitive values at rest (L2)
+24. Add security test coverage (I1)
+25. Implement structured logging with configurable verbosity (I2)
+26. Consider SQLite for auth store (M10)
+27. Remove `TEST_USERS` mechanism (L1)
diff --git a/src/servers/api/pi/pi-bridge.ts b/src/servers/api/pi/pi-bridge.ts
index 112e2d87..d5355803 100644
--- a/src/servers/api/pi/pi-bridge.ts
+++ b/src/servers/api/pi/pi-bridge.ts
@@ -451,6 +451,16 @@ function writeRpcCommand(proc: Subprocess, command: Record<string, unknown>): vo
   }
 }
 
+export function setThinkingLevel(
+  process: Subprocess,
+  level: string,
+): void {
+  writeRpcCommand(process, {
+    type: 'set_thinking_level',
+    level,
+  });
+}
+
 export function sendPrompt(
   process: Subprocess,
   prompt: string,
diff --git a/src/servers/api/pi/types.ts b/src/servers/api/pi/types.ts
index e8f78c40..97ab6ad0 100644
--- a/src/servers/api/pi/types.ts
+++ b/src/servers/api/pi/types.ts
@@ -39,6 +39,8 @@ export type GroupMeta = {
   sessionCount: number;
 };
 
+export type ThinkingLevel = 'off' | 'minimal' | 'low' | 'medium' | 'high' | 'xhigh';
+
 export type ClientMessage =
   | {
       type: "chat";
@@ -50,6 +52,7 @@ export type ClientMessage =
       sandboxed?: boolean;
       groupSlug?: string;
       attachmentIds?: string[];
+      thinking?: ThinkingLevel;
     }
   | {
       type: "resume";
diff --git a/src/servers/api/pi/websocket.ts b/src/servers/api/pi/websocket.ts
index 6eb36cf1..26107059 100644
--- a/src/servers/api/pi/websocket.ts
+++ b/src/servers/api/pi/websocket.ts
@@ -244,7 +244,7 @@ function createEventHandler(sessionId: string, model: string, cwd: string, stora
 
 async function handleChat(
   ws: ServerWebSocket<WSData>,
-  msg: { prompt: string; sessionId?: string; model?: string; cwd?: string; cwdRoot?: string; sandboxed?: boolean; groupSlug?: string; attachmentIds?: string[] }
+  msg: { prompt: string; sessionId?: string; model?: string; cwd?: string; cwdRoot?: string; sandboxed?: boolean; groupSlug?: string; attachmentIds?: string[]; thinking?: string }
 ): Promise<void> {
   const { email, username, userId } = ws.data;
   const sessionId = msg.sessionId || randomUUID();
@@ -312,6 +312,11 @@ async function handleChat(
     session.meta.title = msg.prompt.slice(0, 100);
   }
 
+  // Set thinking level if provided
+  if (msg.thinking) {
+    piBridge.setThinkingLevel(session.piProcess, msg.thinking);
+  }
+
   // Send prompt to Pi
   const requestId = randomUUID();
   session.isGenerating = true;
diff --git a/src/servers/api/server-settings/sync-pi-config.ts b/src/servers/api/server-settings/sync-pi-config.ts
index d4f4d81b..e53aadee 100644
--- a/src/servers/api/server-settings/sync-pi-config.ts
+++ b/src/servers/api/server-settings/sync-pi-config.ts
@@ -75,7 +75,7 @@ export async function syncLocalProvidersToPiConfig(): Promise<void> {
         models: models.map(m => ({
           id: m.id,
           name: m.name || m.id,
-          reasoning: false,
+          reasoning: isReasoningModel(m.id),
           input: ['text'],
           contextWindow: m.contextWindow || 128000,
           maxTokens: m.maxTokens || 4096,
@@ -94,6 +94,20 @@ export async function syncLocalProvidersToPiConfig(): Promise<void> {
   }
 }
 
+/** Detect reasoning-capable models by name patterns */
+const REASONING_PATTERNS = [
+  /\bqwen3\b/i,
+  /\bqwq\b/i,
+  /\bdeepseek-r1\b/i,
+  /\br1\b/i,
+  /\breasoning\b/i,
+  /\bthink/i,
+];
+
+function isReasoningModel(modelId: string): boolean {
+  return REASONING_PATTERNS.some(p => p.test(modelId));
+}
+
 async function fetchModelsFromLocalProvider(
   lp: LocalProvider,
 ): Promise<{ id: string; name?: string; contextWindow?: number; maxTokens?: number }[]> {
diff --git a/src/workspaces/officerdev/src/apps/Chat/ChatLauncher/ChatLauncher.tsx b/src/workspaces/officerdev/src/apps/Chat/ChatLauncher/ChatLauncher.tsx
index 830ed6c1..53c74bbe 100644
--- a/src/workspaces/officerdev/src/apps/Chat/ChatLauncher/ChatLauncher.tsx
+++ b/src/workspaces/officerdev/src/apps/Chat/ChatLauncher/ChatLauncher.tsx
@@ -113,6 +113,8 @@ export function ChatLauncher({
         isConnected={true}
         isGenerating={false}
         hasStarted={false}
+        thinkingLevel={null}
+        onThinkingChange={() => {}}
       />
 
       <WebpageDialog open={urlDialogOpen} onOpenChange={setUrlDialogOpen} onSubmit={attachWebpage} />
diff --git a/src/workspaces/officerdev/src/apps/Chat/EmbeddableChat/useEmbeddableChat.ts b/src/workspaces/officerdev/src/apps/Chat/EmbeddableChat/useEmbeddableChat.ts
index 3b2ff01d..e8a88717 100644
--- a/src/workspaces/officerdev/src/apps/Chat/EmbeddableChat/useEmbeddableChat.ts
+++ b/src/workspaces/officerdev/src/apps/Chat/EmbeddableChat/useEmbeddableChat.ts
@@ -38,7 +38,9 @@ export function useEmbeddableChat(params: UseEmbeddableChatParams) {
     model,
     selectedModel,
     hasStarted,
+    thinkingLevel,
     setSelectedModel,
+    setThinkingLevel,
     sendPrompt,
     stopGeneration,
   } = chat;
@@ -83,6 +85,7 @@ export function useEmbeddableChat(params: UseEmbeddableChatParams) {
       cwdForFirst,
       undefined,
       sandboxed,
+      thinkingLevel,
     );
 
     attachmentManager.clearAttachments();
@@ -197,7 +200,9 @@ export function useEmbeddableChat(params: UseEmbeddableChatParams) {
     model,
     selectedModel,
     hasStarted,
+    thinkingLevel,
     setSelectedModel,
+    setThinkingLevel,
     sendPrompt,
     stopGeneration,
     input,
diff --git a/src/workspaces/officerdev/src/apps/Chat/components/InputArea.tsx b/src/workspaces/officerdev/src/apps/Chat/components/InputArea.tsx
index 88d01779..2f781e4e 100644
--- a/src/workspaces/officerdev/src/apps/Chat/components/InputArea.tsx
+++ b/src/workspaces/officerdev/src/apps/Chat/components/InputArea.tsx
@@ -34,6 +34,8 @@ export const InputArea = ({ manager }: InputAreaProps) => {
     attachImage,
     removeAttachment,
     appendToInput,
+    thinkingLevel,
+    setThinkingLevel,
   } = manager;
 
   const { recording, transcribing, toggleRecording } = useAudioRecording(appendToInput);
@@ -96,6 +98,8 @@ export const InputArea = ({ manager }: InputAreaProps) => {
         isConnected={isConnected}
         isGenerating={isGenerating}
         hasStarted={hasStarted}
+        thinkingLevel={thinkingLevel}
+        onThinkingChange={setThinkingLevel}
       />
 
       <WebpageDialog open={urlDialogOpen} onOpenChange={setUrlDialogOpen} onSubmit={attachWebpage} />
diff --git a/src/workspaces/officerdev/src/apps/Chat/components/ModelSelector.tsx b/src/workspaces/officerdev/src/apps/Chat/components/ModelSelector.tsx
index 0e85235c..03c48746 100644
--- a/src/workspaces/officerdev/src/apps/Chat/components/ModelSelector.tsx
+++ b/src/workspaces/officerdev/src/apps/Chat/components/ModelSelector.tsx
@@ -29,6 +29,8 @@ type ModelSelectorProps = {
   isConnected: boolean;
   isGenerating: boolean;
   hasStarted: boolean;
+  thinkingLevel: string | null;
+  onThinkingChange: (level: string | null) => void;
 };
 
 export function ModelSelector({
@@ -40,6 +42,8 @@ export function ModelSelector({
   isConnected,
   isGenerating,
   hasStarted,
+  thinkingLevel,
+  onThinkingChange,
 }: ModelSelectorProps) {
   const providers = [...new Set(availableModels.map((m) => m.provider).filter(Boolean))] as string[];
 
@@ -99,28 +103,57 @@ export function ModelSelector({
           ))}
         </div>
       )}
-      <div className="text-xs text-duck-dark/50">
-        {providerModels.length > 0 ? (
-          <Select
-            value={displayModel ?? fallbackModelId ?? undefined}
-            onValueChange={(v) => !isLocked && onModelChange(v)}
-            disabled={isLocked}
-          >
-            <SelectTrigger className="h-auto border-0 bg-transparent p-0 text-xs text-duck-dark/50 shadow-none focus:ring-0 gap-1 cursor-pointer">
-              <SelectValue />
-            </SelectTrigger>
-            <SelectContent className="z-[800]" side="top">
-              {providerModels.map((m) => (
-                <SelectItem key={m.id} value={m.id}>
-                  {m.name}
-                </SelectItem>
-              ))}
-            </SelectContent>
-          </Select>
-        ) : (
-          <span>{getModelDisplayText()}</span>
+      <div className="flex items-center gap-2">
+        {availableModels.find((m) => m.id === displayModel)?.reasoning && (
+          <ThinkingToggle enabled={thinkingLevel === 'high'} onToggle={() => onThinkingChange(thinkingLevel === 'high' ? 'off' : 'high')} disabled={isGenerating} />
         )}
+        <div className="text-xs text-duck-dark/50">
+          {providerModels.length > 0 ? (
+            <Select
+              value={displayModel ?? fallbackModelId ?? undefined}
+              onValueChange={(v) => !isLocked && onModelChange(v)}
+              disabled={isLocked}
+            >
+              <SelectTrigger className="h-auto border-0 bg-transparent p-0 text-xs text-duck-dark/50 shadow-none focus:ring-0 gap-1 cursor-pointer">
+                <SelectValue />
+              </SelectTrigger>
+              <SelectContent className="z-[800]" side="top">
+                {providerModels.map((m) => (
+                  <SelectItem key={m.id} value={m.id}>
+                    {m.name}
+                  </SelectItem>
+                ))}
+              </SelectContent>
+            </Select>
+          ) : (
+            <span>{getModelDisplayText()}</span>
+          )}
+        </div>
       </div>
     </div>
   );
 }
+
+// ── Thinking Toggle ──
+
+type ThinkingToggleProps = {
+  enabled: boolean;
+  onToggle: () => void;
+  disabled: boolean;
+};
+
+const ThinkingToggle = ({ enabled, onToggle, disabled }: ThinkingToggleProps) => (
+  <button
+    type="button"
+    onClick={onToggle}
+    disabled={disabled}
+    title={enabled ? 'Thinking enabled (click to disable)' : 'Thinking disabled (click to enable)'}
+    className={`rounded-md px-2 py-0.5 text-xs font-medium transition-colors cursor-pointer disabled:opacity-40 disabled:cursor-not-allowed ${
+      enabled
+        ? 'bg-duck-teal/15 text-duck-teal'
+        : 'text-duck-dark/40 hover:text-duck-dark/60'
+    }`}
+  >
+    {enabled ? 'think' : 'no think'}
+  </button>
+);
diff --git a/src/workspaces/officerdev/src/apps/FileBrowser/FileBrowserApp/components/TaskRunnerModal.tsx b/src/workspaces/officerdev/src/apps/FileBrowser/FileBrowserApp/components/TaskRunnerModal.tsx
index 1e42263b..9eb67099 100644
--- a/src/workspaces/officerdev/src/apps/FileBrowser/FileBrowserApp/components/TaskRunnerModal.tsx
+++ b/src/workspaces/officerdev/src/apps/FileBrowser/FileBrowserApp/components/TaskRunnerModal.tsx
@@ -135,6 +135,8 @@ const PiMonoInner = ({ defaultInput, cwd, initialModel, taskInfo, sandboxed }: P
             isConnected={chat.isConnected}
             isGenerating={false}
             hasStarted={false}
+            thinkingLevel={chat.thinkingLevel}
+            onThinkingChange={chat.setThinkingLevel}
           />
         </div>
       </>
diff --git a/src/workspaces/officerdev/src/hooks/usePiChat.ts b/src/workspaces/officerdev/src/hooks/usePiChat.ts
index 3e6b00f3..32ad6912 100644
--- a/src/workspaces/officerdev/src/hooks/usePiChat.ts
+++ b/src/workspaces/officerdev/src/hooks/usePiChat.ts
@@ -28,6 +28,7 @@ export function usePiChat(initialSessionId?: string, initialModel?: string | nul
   const [model, setModel] = useState<string | null>(null);
   const [selectedModel, setSelectedModel] = useState<string | null>(initialModel ?? null);
   const [cwd, setCwd] = useState<string | null>(null);
+  const [thinkingLevel, setThinkingLevel] = useState<string | null>(null);
 
   // Track if session has started (first message sent)
   const [hasStarted, setHasStarted] = useState(false);
@@ -265,6 +266,7 @@ export function usePiChat(initialSessionId?: string, initialModel?: string | nul
     cwdParam?: { root?: string; path: string },
     groupSlug?: string | null,
     sandboxed?: boolean,
+    thinking?: string | null,
   ) {
     // Mark session as started on first message
     if (!hasStarted) {
@@ -297,6 +299,7 @@ export function usePiChat(initialSessionId?: string, initialModel?: string | nul
       ...(imageData?.length ? { images: imageData } : {}),
       ...(resourceChatDir ? { resourceChatDir } : {}),
       ...(taskInfo ? { taskInfo } : {}),
+      ...(thinking ? { thinking } : {}),
     });
   }
 
@@ -314,7 +317,9 @@ export function usePiChat(initialSessionId?: string, initialModel?: string | nul
     selectedModel,
     hasStarted,
     cwd,
+    thinkingLevel,
     setSelectedModel,
+    setThinkingLevel,
     sendPrompt,
     stopGeneration,
   };