diff --git a/src/commands/install-skill.ts b/src/commands/install-skill.ts
index 58611424..02f4ac39 100644
--- a/src/commands/install-skill.ts
+++ b/src/commands/install-skill.ts
@@ -1,9 +1,9 @@
 import { homedir } from 'os';
-import { join, dirname } from 'path';
+import { join } from 'path';
 import { existsSync } from 'fs';
 import { mkdir, copyFile, readdir } from 'fs/promises';
-import { fileURLToPath } from 'url';
 import chalk from 'chalk';
+import { getPackageRoot } from '../utils/paths.js';
 
 export interface AgentConfig {
   name: string;
@@ -48,9 +48,7 @@ export interface InstallSkillOptions {
 }
 
 export function getSkillsDir(): string {
-  const currentFile = fileURLToPath(import.meta.url);
-  // From dist/src/commands/install-skill.js -> skills/
-  return join(dirname(currentFile), '..', '..', '..', 'skills');
+  return join(getPackageRoot(import.meta.url), 'skills');
 }
 
 export async function discoverSkills(skillsDir: string): Promise<string[]> {
diff --git a/src/lib/agent-interface.ts b/src/lib/agent-interface.ts
index 649f53da..33a73bfb 100644
--- a/src/lib/agent-interface.ts
+++ b/src/lib/agent-interface.ts
@@ -4,7 +4,7 @@
  */
 
 import path from 'path';
-import { fileURLToPath } from 'url';
+import { getPackageRoot } from '../utils/paths.js';
 import { debug, logInfo, logWarn, logError, initLogFile, getLogFilePath } from '../utils/debug.js';
 import type { InstallerOptions } from '../utils/types.js';
 import { analytics } from '../utils/analytics.js';
@@ -577,10 +577,7 @@ export async function runAgent(
     };
 
     // Load plugin with bundled skills
-    // Path from dist/lib/ back to package root
-    const __filename = fileURLToPath(import.meta.url);
-    const __dirname = path.dirname(__filename);
-    const pluginPath = path.join(__dirname, '../..');
+    const pluginPath = getPackageRoot(import.meta.url);
     logInfo('Loading plugin from:', pluginPath);
 
     const response = query({
diff --git a/src/utils/paths.ts b/src/utils/paths.ts
new file mode 100644
index 00000000..b81d9e05
--- /dev/null
+++ b/src/utils/paths.ts
@@ -0,0 +1,18 @@
+import { dirname, join } from 'path';
+import { existsSync } from 'fs';
+import { fileURLToPath } from 'url';
+
+/**
+ * Resolve the package root by walking up from a compiled file until we find package.json.
+ * Immune to changes in tsconfig outDir/rootDir structure.
+ */
+export function getPackageRoot(metaUrl: string): string {
+  let dir = dirname(fileURLToPath(metaUrl));
+  while (dir !== dirname(dir)) {
+    if (existsSync(join(dir, 'package.json'))) {
+      return dir;
+    }
+    dir = dirname(dir);
+  }
+  throw new Error('Could not find package root (no package.json found in parent directories)');
+}