diff --git a/apps/frontend/src/main/cli-tool-manager.ts b/apps/frontend/src/main/cli-tool-manager.ts
index e54dd43b..4e0c6d0a 100644
--- a/apps/frontend/src/main/cli-tool-manager.ts
+++ b/apps/frontend/src/main/cli-tool-manager.ts
@@ -27,6 +27,7 @@ import os from 'os';
 import { app } from 'electron';
 import { findExecutable } from './env-utils';
 import type { ToolDetectionResult } from '../shared/types';
+import { findHomebrewPython as findHomebrewPythonUtil } from './utils/homebrew-python';
 
 /**
  * Supported CLI tools managed by this system
@@ -731,37 +732,15 @@ class CLIToolManager {
 
   /**
    * Find Homebrew Python on macOS
-   *
-   * Checks both Apple Silicon and Intel Homebrew locations.
-   * Searches for python3, python3.13, python3.12, etc. in order.
+   * Delegates to shared utility function.
    *
    * @returns Path to Homebrew Python or null if not found
    */
   private findHomebrewPython(): string | null {
-    const homebrewDirs = [
-      '/opt/homebrew/bin', // Apple Silicon
-      '/usr/local/bin', // Intel Mac
-    ];
-
-    // Check for generic python3 first, then specific versions (newest first)
-    const pythonNames = [
-      'python3',
-      'python3.13',
-      'python3.12',
-      'python3.11',
-      'python3.10',
-    ];
-
-    for (const dir of homebrewDirs) {
-      for (const name of pythonNames) {
-        const pythonPath = path.join(dir, name);
-        if (existsSync(pythonPath)) {
-          return pythonPath;
-        }
-      }
-    }
-
-    return null;
+    return findHomebrewPythonUtil(
+      (pythonPath) => this.validatePython(pythonPath),
+      '[CLI Tools]'
+    );
   }
 
   /**
diff --git a/apps/frontend/src/main/python-detector.ts b/apps/frontend/src/main/python-detector.ts
index f8c80d20..e15bcd45 100644
--- a/apps/frontend/src/main/python-detector.ts
+++ b/apps/frontend/src/main/python-detector.ts
@@ -2,6 +2,7 @@ import { execSync, execFileSync } from 'child_process';
 import { existsSync, accessSync, constants } from 'fs';
 import path from 'path';
 import { app } from 'electron';
+import { findHomebrewPython as findHomebrewPythonUtil } from './utils/homebrew-python';
 
 /**
  * Get the path to the bundled Python executable.
@@ -34,23 +35,12 @@ export function getBundledPythonPath(): string | null {
 
 /**
  * Find the first existing Homebrew Python installation.
- * Checks common Homebrew paths for Python 3.
+ * Delegates to shared utility function.
  *
  * @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 pythonPath of homebrewPaths) {
-    if (existsSync(pythonPath)) {
-      return pythonPath;
-    }
-  }
-
-  return null;
+  return findHomebrewPythonUtil(validatePythonVersion, '[Python]');
 }
 
 /**
@@ -308,6 +298,7 @@ const ALLOWED_PATH_PATTERNS: RegExp[] = [
 /**
  * Known safe Python commands (not full paths).
  * These are resolved by the shell/OS and are safe.
+ * Note: Update this list when new Python versions are released.
  */
 const SAFE_PYTHON_COMMANDS = new Set([
   'python',
@@ -316,6 +307,7 @@ const SAFE_PYTHON_COMMANDS = new Set([
   'python3.11',
   'python3.12',
   'python3.13',
+  'python3.14',
   'py',
   'py -3',
 ]);
diff --git a/apps/frontend/src/main/utils/homebrew-python.ts b/apps/frontend/src/main/utils/homebrew-python.ts
new file mode 100644
index 00000000..9891c123
--- /dev/null
+++ b/apps/frontend/src/main/utils/homebrew-python.ts
@@ -0,0 +1,77 @@
+/**
+ * Homebrew Python Detection Utility
+ *
+ * Shared logic for finding Python installations in Homebrew directories.
+ * Used by both python-detector.ts and cli-tool-manager.ts to ensure
+ * consistent Python detection across the application.
+ */
+
+import { existsSync } from 'fs';
+import path from 'path';
+
+/**
+ * Validation result for a Python installation.
+ */
+export interface PythonValidation {
+  valid: boolean;
+  version?: string;
+  message: string;
+}
+
+/**
+ * Find the first valid Homebrew Python installation.
+ * Checks common Homebrew paths for Python 3, including versioned installations.
+ * Prioritizes newer Python versions (3.14, 3.13, 3.12, 3.11, 3.10).
+ *
+ * Note: This list should be updated when new Python versions are released.
+ * Check for specific versions first to ensure we find the latest available version.
+ *
+ * @param validateFn - Function to validate a Python path and return validation result
+ * @param logPrefix - Prefix for log messages (e.g., '[Python]', '[CLI Tools]')
+ * @returns The path to Homebrew Python, or null if not found
+ */
+export function findHomebrewPython(
+  validateFn: (pythonPath: string) => PythonValidation,
+  logPrefix: string
+): string | null {
+  const homebrewDirs = [
+    '/opt/homebrew/bin',  // Apple Silicon (M1/M2/M3)
+    '/usr/local/bin'      // Intel Mac
+  ];
+
+  // Check for specific Python versions first (newest to oldest), then fall back to generic python3.
+  // This ensures we find the latest available version that meets our requirements.
+  const pythonNames = [
+    'python3.14',
+    'python3.13',
+    'python3.12',
+    'python3.11',
+    'python3.10',
+    'python3',
+  ];
+
+  for (const dir of homebrewDirs) {
+    for (const name of pythonNames) {
+      const pythonPath = path.join(dir, name);
+      if (existsSync(pythonPath)) {
+        try {
+          // Validate that this Python meets version requirements
+          const validation = validateFn(pythonPath);
+          if (validation.valid) {
+            console.log(`${logPrefix} Found valid Homebrew Python: ${pythonPath} (${validation.version})`);
+            return pythonPath;
+          } else {
+            console.warn(`${logPrefix} ${pythonPath} rejected: ${validation.message}`);
+          }
+        } catch (error) {
+          // Version check failed (e.g., timeout, permission issue), try next candidate
+          console.warn(`${logPrefix} Failed to validate ${pythonPath}: ${error}`);
+          continue;
+        }
+      }
+    }
+  }
+
+  console.log(`${logPrefix} No valid Homebrew Python found in ${homebrewDirs.join(', ')}`);
+  return null;
+}