diff --git a/src/servers/sidecar/pi/pi-manager.ts b/src/servers/sidecar/pi/pi-manager.ts
index 6fbbada5..9e9d0658 100644
--- a/src/servers/sidecar/pi/pi-manager.ts
+++ b/src/servers/sidecar/pi/pi-manager.ts
@@ -1,9 +1,17 @@
-import { join } from 'node:path';
+import { join, dirname } from 'node:path';
 import { readdirSync, existsSync, mkdirSync } from 'node:fs';
 import type { Subprocess } from 'bun';
 import type { PiEvent, MessageCost } from '../../api/pi/types';
 import type { PiSpawnParams, PiSessionInfo } from '../protocol';
-import { buildSandboxPrefix, buildRunuserSuffix, SANDBOX_DATA, SANDBOX_HOME } from '../sandbox';
+import {
+  buildSandboxPrefix,
+  buildRunuserSuffix,
+  SANDBOX_DATA,
+  SANDBOX_GLOBAL_EXTENSIONS,
+  SANDBOX_GLOBAL_SKILLS,
+  SANDBOX_GLOBAL_TOOLS,
+  SANDBOX_HOME,
+} from '../sandbox';
 
 const DATA_PATH = process.env.DATA_PATH ?? join(process.cwd(), 'data');
 const PI_CONFIG_DIR = join(require('node:os').homedir(), '.pi', 'agent');
@@ -41,6 +49,22 @@ const PI_CMD = (() => {
   return [piBin];
 })();
 
+// Pi's nested node_modules — needed for NODE_PATH so extensions can resolve Pi's dependencies
+// (e.g. @sinclair/typebox used by the tool-loader extension)
+const PI_NODE_MODULES = (() => {
+  const whichResult = Bun.spawnSync({ cmd: ['which', 'pi'], stdout: 'pipe', stderr: 'ignore' });
+  const piBin = whichResult.stdout.toString().trim() || 'pi';
+  const readlinkResult = Bun.spawnSync({ cmd: ['readlink', '-f', piBin], stdout: 'pipe', stderr: 'ignore' });
+  const realPath = readlinkResult.stdout.toString().trim();
+  // cli.js is at .../pi-coding-agent/dist/cli.js — node_modules is at .../pi-coding-agent/node_modules
+  if (realPath) {
+    const pkgDir = join(dirname(realPath), '..');
+    const nm = join(pkgDir, 'node_modules');
+    if (existsSync(nm)) return nm;
+  }
+  return null;
+})();
+
 // Active Pi processes
 type PiSession = {
   sessionId: string;
@@ -56,34 +80,46 @@ const sessions = new Map<string, PiSession>();
 
 // ── Helpers ──
 
-function collectSkillFlags(email: string): string[] {
+function collectSkillFlagsFromDir(scanDir: string, targetDir: string): string[] {
   const flags: string[] = [];
-  const dirs = [getGlobalSkillsDir(), getUserSkillsDir(email)];
-  for (const dir of dirs) {
-    if (!existsSync(dir)) continue;
-    for (const entry of readdirSync(dir, { withFileTypes: true })) {
-      if (!entry.isDirectory()) continue;
-      if (existsSync(join(dir, entry.name, 'SKILL.md'))) {
-        flags.push('--skill', `${dir}/${entry.name}`);
-      }
+  if (!existsSync(scanDir)) return flags;
+
+  for (const entry of readdirSync(scanDir, { withFileTypes: true })) {
+    if (!entry.isDirectory()) continue;
+    if (existsSync(join(scanDir, entry.name, 'SKILL.md'))) {
+      flags.push('--skill', `${targetDir}/${entry.name}`);
     }
   }
+
+  return flags;
+}
+
+function collectSkillFlags(email: string): string[] {
+  return [
+    ...collectSkillFlagsFromDir(getGlobalSkillsDir(), getGlobalSkillsDir()),
+    ...collectSkillFlagsFromDir(getUserSkillsDir(email), getUserSkillsDir(email)),
+  ];
+}
+
+function collectExtensionFlagsFromDir(scanDir: string, targetDir: string): string[] {
+  const flags: string[] = [];
+  if (!existsSync(scanDir)) return flags;
+
+  for (const entry of readdirSync(scanDir, { withFileTypes: true })) {
+    if (!entry.isDirectory()) continue;
+    if (existsSync(join(scanDir, entry.name, 'index.ts'))) {
+      flags.push('--extension', `${targetDir}/${entry.name}/index.ts`);
+    }
+  }
+
   return flags;
 }
 
 function collectExtensionFlags(email: string): string[] {
-  const flags: string[] = [];
-  const dirs = [getGlobalExtensionsDir(), getUserExtensionsDir(email)];
-  for (const dir of dirs) {
-    if (!existsSync(dir)) continue;
-    for (const entry of readdirSync(dir, { withFileTypes: true })) {
-      if (!entry.isDirectory()) continue;
-      if (existsSync(join(dir, entry.name, 'index.ts'))) {
-        flags.push('--extension', `${dir}/${entry.name}/index.ts`);
-      }
-    }
-  }
-  return flags;
+  return [
+    ...collectExtensionFlagsFromDir(getGlobalExtensionsDir(), getGlobalExtensionsDir()),
+    ...collectExtensionFlagsFromDir(getUserExtensionsDir(email), getUserExtensionsDir(email)),
+  ];
 }
 
 async function resolveApiKeyForModel(model: string): Promise<string | null> {
@@ -237,8 +273,19 @@ export type PiSpawnOptions = {
 export async function spawnPi(options: PiSpawnOptions): Promise<void> {
   const { sessionId, email, userId, username, role, cwd, model, sessionFile, onEvent } = options;
 
-  const skillFlags = collectSkillFlags(email);
-  const extensionFlags = collectExtensionFlags(email);
+  const isSuperAdmin = role === 'Super Admin';
+  const skillFlags = isSuperAdmin
+    ? collectSkillFlags(email)
+    : [
+        ...collectSkillFlagsFromDir(getGlobalSkillsDir(), SANDBOX_GLOBAL_SKILLS),
+        ...collectSkillFlagsFromDir(getUserSkillsDir(email), `${SANDBOX_DATA}/skills`),
+      ];
+  const extensionFlags = isSuperAdmin
+    ? collectExtensionFlags(email)
+    : [
+        ...collectExtensionFlagsFromDir(getGlobalExtensionsDir(), SANDBOX_GLOBAL_EXTENSIONS),
+        ...collectExtensionFlagsFromDir(getUserExtensionsDir(email), `${SANDBOX_DATA}/extensions`),
+      ];
 
   const piArgs = [
     ...PI_CMD,
@@ -260,7 +307,6 @@ export async function spawnPi(options: PiSpawnOptions): Promise<void> {
     mkdirSync(cwd, { recursive: true });
   }
 
-  const isSuperAdmin = role === 'Super Admin';
   const homeDir = getHomeDirForRole(email, role);
   const toolsDirs = [getGlobalToolsDir(), getUserToolsDir(email)].join(':');
 
@@ -269,7 +315,7 @@ export async function spawnPi(options: PiSpawnOptions): Promise<void> {
   if (isSuperAdmin) {
     // Super Admin: run directly with host env, no sandbox
     const env: Record<string, string> = {
-      ...process.env as Record<string, string>,
+      ...(process.env as Record<string, string>),
       HOME: process.env.HOME ?? homeDir,
       OFFICER_USER_HOME: homeDir,
       OFFICER_USER_ROOT: join(DATA_PATH, email),
@@ -278,11 +324,12 @@ export async function spawnPi(options: PiSpawnOptions): Promise<void> {
       OFFICER_EMAIL_DB: join(DATA_PATH, email, 'emails.db'),
       TERM: 'xterm-256color',
     };
+    if (PI_NODE_MODULES) env.NODE_PATH = PI_NODE_MODULES;
 
     proc = Bun.spawn(piArgs, { cwd, stdin: 'pipe', stdout: 'pipe', stderr: 'pipe', env });
   } else {
     // Non-admin: run inside bwrap sandbox
-    const sandboxToolsDirs = [getGlobalToolsDir(), `${SANDBOX_DATA}/tools`].join(':');
+    const sandboxToolsDirs = [SANDBOX_GLOBAL_TOOLS, `${SANDBOX_DATA}/tools`].join(':');
     const prefix = buildSandboxPrefix(email);
 
     // Pi-specific env vars
@@ -292,6 +339,7 @@ export async function spawnPi(options: PiSpawnOptions): Promise<void> {
     prefix.push('--setenv', 'PI_TOOLS_DIRS', sandboxToolsDirs);
     prefix.push('--setenv', 'OFFICER_EMAIL_DB', `${SANDBOX_DATA}/emails.db`);
     prefix.push('--setenv', 'TERM', 'xterm-256color');
+    if (PI_NODE_MODULES) prefix.push('--setenv', 'NODE_PATH', PI_NODE_MODULES);
 
     const sandboxArgs = [...prefix, ...buildRunuserSuffix()];
     proc = Bun.spawn([...sandboxArgs, ...piArgs], { stdin: 'pipe', stdout: 'pipe', stderr: 'pipe' });
diff --git a/src/servers/sidecar/sandbox.ts b/src/servers/sidecar/sandbox.ts
index dc0f54ac..b61535da 100644
--- a/src/servers/sidecar/sandbox.ts
+++ b/src/servers/sidecar/sandbox.ts
@@ -17,15 +17,20 @@ const OS_USERNAME = (() => {
   return result.stdout.toString().trim() || 'pastilhas';
 })();
 
-// Sandbox mount point for user data (short path avoids intermediate dir traversal issues)
+// Sandbox mount points
 export const SANDBOX_DATA = '/data';
 export const SANDBOX_HOME = `${SANDBOX_DATA}/home`;
+export const SANDBOX_GLOBAL_ROOT = '/officer';
+export const SANDBOX_GLOBAL_SKILLS = `${SANDBOX_GLOBAL_ROOT}/skills`;
+export const SANDBOX_GLOBAL_EXTENSIONS = `${SANDBOX_GLOBAL_ROOT}/extensions`;
+export const SANDBOX_GLOBAL_TOOLS = `${SANDBOX_GLOBAL_ROOT}/tools`;
 
 // Build bwrap sandbox prefix for a given user email.
 // Returns args up to (but not including) the `-- runuser` suffix.
 // Callers can append extra `--setenv` args before calling `buildRunuserSuffix()`.
 export function buildSandboxPrefix(email: string): string[] {
   const userDataDir = join(DATA_PATH, email);
+  const globalSkillsDir = join(DATA_PATH, 'skills');
   const globalToolsDir = join(DATA_PATH, 'tools');
   const globalExtensionsDir = join(DATA_PATH, 'extensions');
 
@@ -83,10 +88,23 @@ export function buildSandboxPrefix(email: string): string[] {
   // Project source (for MCP server)
   args.push('--ro-bind', PROJECT_ROOT, PROJECT_ROOT);
 
-  // Global tools/extensions (read-only, mounted at original paths for MCP config references)
+  // Ensure DATA_PATH intermediate dirs are traversable (same issue as HOME)
+  args.push('--perms', '0755', '--dir', DATA_PATH);
+
+  // Global content mounted at original paths for existing host-path references
+  if (existsSync(globalSkillsDir)) args.push('--ro-bind', globalSkillsDir, globalSkillsDir);
   if (existsSync(globalToolsDir)) args.push('--ro-bind', globalToolsDir, globalToolsDir);
   if (existsSync(globalExtensionsDir)) args.push('--ro-bind', globalExtensionsDir, globalExtensionsDir);
 
+  // Ensure sandbox-local global root is traversable before mounting nested paths under it.
+  args.push('--perms', '0755', '--dir', SANDBOX_GLOBAL_ROOT);
+
+  // Global content also mounted at short sandbox-local paths so nested imports do not
+  // depend on traversing host-specific parent directories created by bwrap.
+  if (existsSync(globalSkillsDir)) args.push('--ro-bind', globalSkillsDir, SANDBOX_GLOBAL_SKILLS);
+  if (existsSync(globalToolsDir)) args.push('--ro-bind', globalToolsDir, SANDBOX_GLOBAL_TOOLS);
+  if (existsSync(globalExtensionsDir)) args.push('--ro-bind', globalExtensionsDir, SANDBOX_GLOBAL_EXTENSIONS);
+
   // User data (read-write, mounted at /data to avoid intermediate dir permission issues)
   args.push('--bind', userDataDir, SANDBOX_DATA);