diff --git a/apps/frontend/package-lock.json b/apps/frontend/package-lock.json
index d8a0c0e3..81c474c3 100644
--- a/apps/frontend/package-lock.json
+++ b/apps/frontend/package-lock.json
@@ -65,7 +65,7 @@
         "@types/uuid": "^10.0.0",
         "@vitejs/plugin-react": "^5.1.2",
         "autoprefixer": "^10.4.22",
-        "electron": "^39.2.6",
+        "electron": "^39.2.7",
         "electron-builder": "^26.0.12",
         "electron-vite": "^5.0.0",
         "eslint": "^9.39.1",
diff --git a/apps/frontend/package.json b/apps/frontend/package.json
index 77eb83d0..7ab47e33 100644
--- a/apps/frontend/package.json
+++ b/apps/frontend/package.json
@@ -149,7 +149,7 @@
       },
       {
         "from": "../backend",
-        "to": "auto-claude",
+        "to": "backend",
         "filter": [
           "!**/.git",
           "!**/__pycache__",
diff --git a/apps/frontend/src/main/ipc-handlers/context/project-context-handlers.ts b/apps/frontend/src/main/ipc-handlers/context/project-context-handlers.ts
index 217566c0..162ce35f 100644
--- a/apps/frontend/src/main/ipc-handlers/context/project-context-handlers.ts
+++ b/apps/frontend/src/main/ipc-handlers/context/project-context-handlers.ts
@@ -21,7 +21,7 @@ import {
   buildMemoryStatus
 } from './memory-status-handlers';
 import { loadFileBasedMemories } from './memory-data-handlers';
-import { parsePythonCommand } from '../../python-detector';
+import { findPythonCommand, parsePythonCommand } from '../../python-detector';
 
 /**
  * Load project index from file
@@ -159,7 +159,7 @@ export function registerProjectContextHandlers(
         const indexOutputPath = path.join(project.path, AUTO_BUILD_PATHS.PROJECT_INDEX);
 
         // Get Python command directly from settings file (not pythonEnvManager which creates NEW venv)
-        let pythonCmd = 'python3';
+        let pythonCmd = findPythonCommand() || 'python3';
         try {
           const settingsPath = path.join(app.getPath('userData'), 'settings.json');
           if (existsSync(settingsPath)) {
diff --git a/apps/frontend/src/main/python-detector.ts b/apps/frontend/src/main/python-detector.ts
index 55cea55e..a9046c78 100644
--- a/apps/frontend/src/main/python-detector.ts
+++ b/apps/frontend/src/main/python-detector.ts
@@ -1,6 +1,27 @@
 import { execSync } from 'child_process';
 import { existsSync } from 'fs';
 
+/**
+ * Find the first existing Homebrew Python installation.
+ * Checks common Homebrew paths for Python 3.
+ *
+ * @returns The path to Homebrew Python, or null if not found
+ */
+function findHomebrewPython(): string | null {
+  const homebrewPaths = [
+    '/opt/homebrew/bin/python3',  // Apple Silicon (M1/M2/M3)
+    '/usr/local/bin/python3'      // Intel Mac
+  ];
+
+  for (const path of homebrewPaths) {
+    if (existsSync(path)) {
+      return path;
+    }
+  }
+
+  return null;
+}
+
 /**
  * Detect and return the best available Python command.
  * Tries multiple candidates and returns the first one that works with Python 3.
@@ -10,11 +31,16 @@ import { existsSync } from 'fs';
 export function findPythonCommand(): string | null {
   const isWindows = process.platform === 'win32';
 
-  // On Windows, try py launcher first (most reliable), then python, then python3
-  // On Unix, try python3 first, then python
-  const candidates = isWindows
-    ? ['py -3', 'python', 'python3', 'py']
-    : ['python3', 'python'];
+  // Build candidate list prioritizing Homebrew Python on macOS
+  let candidates: string[];
+  if (isWindows) {
+    candidates = ['py -3', 'python', 'python3', 'py'];
+  } else {
+    const homebrewPython = findHomebrewPython();
+    candidates = homebrewPython
+      ? [homebrewPython, 'python3', 'python']
+      : ['python3', 'python'];
+  }
 
   for (const cmd of candidates) {
     try {
@@ -35,7 +61,10 @@ export function findPythonCommand(): string | null {
   }
 
   // Fallback to platform-specific default
-  return isWindows ? 'python' : 'python3';
+  if (isWindows) {
+    return 'python';
+  }
+  return findHomebrewPython() || 'python3';
 }
 
 /**
@@ -110,7 +139,10 @@ function validatePythonVersion(pythonCmd: string): {
  * @returns The default Python command for this platform
  */
 export function getDefaultPythonCommand(): string {
-  return process.platform === 'win32' ? 'python' : 'python3';
+  if (process.platform === 'win32') {
+    return 'python';
+  }
+  return findHomebrewPython() || 'python3';
 }
 
 /**