diff --git a/apps/frontend/package.json b/apps/frontend/package.json
index 4fdab9c3..ef847bd5 100644
--- a/apps/frontend/package.json
+++ b/apps/frontend/package.json
@@ -114,7 +114,7 @@
     "@vitejs/plugin-react": "^5.1.2",
     "autoprefixer": "^10.4.22",
     "cross-env": "^10.1.0",
-    "electron": "^39.2.7",
+    "electron": "39.2.7",
     "electron-builder": "^26.0.12",
     "electron-vite": "^5.0.0",
     "eslint": "^9.39.1",
diff --git a/apps/frontend/src/main/changelog/generator.ts b/apps/frontend/src/main/changelog/generator.ts
index c71af9c3..6fa75c06 100644
--- a/apps/frontend/src/main/changelog/generator.ts
+++ b/apps/frontend/src/main/changelog/generator.ts
@@ -13,6 +13,7 @@ import { extractChangelog } from './parser';
 import { getCommits, getBranchDiffCommits } from './git-integration';
 import { detectRateLimit, createSDKRateLimitInfo, getProfileEnv } from '../rate-limit-detector';
 import { parsePythonCommand } from '../python-detector';
+import { getAugmentedEnv } from '../env-utils';
 
 /**
  * Core changelog generation logic
@@ -246,21 +247,9 @@ export class ChangelogGenerator extends EventEmitter {
     const homeDir = os.homedir();
     const isWindows = process.platform === 'win32';
 
-    // Build PATH with platform-appropriate separator and locations
-    const pathAdditions = isWindows
-      ? [
-          path.join(homeDir, 'AppData', 'Local', 'Programs', 'claude'),
-          path.join(homeDir, 'AppData', 'Roaming', 'npm'),
-          path.join(homeDir, '.local', 'bin'),
-          'C:\\Program Files\\Claude',
-          'C:\\Program Files (x86)\\Claude'
-        ]
-      : [
-          '/usr/local/bin',
-          '/opt/homebrew/bin',
-          path.join(homeDir, '.local', 'bin'),
-          path.join(homeDir, 'bin')
-        ];
+    // Use getAugmentedEnv() to ensure common tool paths are available
+    // even when app is launched from Finder/Dock
+    const augmentedEnv = getAugmentedEnv();
 
     // Get active Claude profile environment (OAuth token preferred, falls back to CLAUDE_CONFIG_DIR)
     const profileEnv = getProfileEnv();
@@ -271,15 +260,13 @@ export class ChangelogGenerator extends EventEmitter {
     });
 
     const spawnEnv: Record<string, string> = {
-      ...process.env as Record<string, string>,
+      ...augmentedEnv,
       ...this.autoBuildEnv,
       ...profileEnv, // Include active Claude profile config
       // Ensure critical env vars are set for claude CLI
       // Use USERPROFILE on Windows, HOME on Unix
       ...(isWindows ? { USERPROFILE: homeDir } : { HOME: homeDir }),
       USER: process.env.USER || process.env.USERNAME || 'user',
-      // Add common binary locations to PATH for claude CLI
-      PATH: [process.env.PATH || '', ...pathAdditions].filter(Boolean).join(path.delimiter),
       PYTHONUNBUFFERED: '1',
       PYTHONIOENCODING: 'utf-8',
       PYTHONUTF8: '1'
diff --git a/apps/frontend/src/main/changelog/version-suggester.ts b/apps/frontend/src/main/changelog/version-suggester.ts
index 4869fe41..027df15f 100644
--- a/apps/frontend/src/main/changelog/version-suggester.ts
+++ b/apps/frontend/src/main/changelog/version-suggester.ts
@@ -4,6 +4,7 @@ import * as os from 'os';
 import type { GitCommit } from '../../shared/types';
 import { getProfileEnv } from '../rate-limit-detector';
 import { parsePythonCommand } from '../python-detector';
+import { getAugmentedEnv } from '../env-utils';
 
 interface VersionSuggestion {
   version: string;
@@ -215,31 +216,19 @@ except Exception as e:
     const homeDir = os.homedir();
     const isWindows = process.platform === 'win32';
 
-    // Build PATH with platform-appropriate separator and locations
-    const pathAdditions = isWindows
-      ? [
-          path.join(homeDir, 'AppData', 'Local', 'Programs', 'claude'),
-          path.join(homeDir, 'AppData', 'Roaming', 'npm'),
-          path.join(homeDir, '.local', 'bin'),
-          'C:\\Program Files\\Claude',
-          'C:\\Program Files (x86)\\Claude'
-        ]
-      : [
-          '/usr/local/bin',
-          '/opt/homebrew/bin',
-          path.join(homeDir, '.local', 'bin'),
-          path.join(homeDir, 'bin')
-        ];
+    // Use getAugmentedEnv() to ensure common tool paths are available
+    // even when app is launched from Finder/Dock
+    const augmentedEnv = getAugmentedEnv();
 
     // Get active Claude profile environment
     const profileEnv = getProfileEnv();
 
     const spawnEnv: Record<string, string> = {
-      ...process.env as Record<string, string>,
+      ...augmentedEnv,
       ...profileEnv,
+      // Ensure critical env vars are set for claude CLI
       ...(isWindows ? { USERPROFILE: homeDir } : { HOME: homeDir }),
       USER: process.env.USER || process.env.USERNAME || 'user',
-      PATH: [process.env.PATH || '', ...pathAdditions].filter(Boolean).join(path.delimiter),
       PYTHONUNBUFFERED: '1',
       PYTHONIOENCODING: 'utf-8',
       PYTHONUTF8: '1'
diff --git a/apps/frontend/src/main/insights/config.ts b/apps/frontend/src/main/insights/config.ts
index 0ca1609c..3ef00f30 100644
--- a/apps/frontend/src/main/insights/config.ts
+++ b/apps/frontend/src/main/insights/config.ts
@@ -3,7 +3,8 @@ import { existsSync, readFileSync } from 'fs';
 import { app } from 'electron';
 import { getProfileEnv } from '../rate-limit-detector';
 import { getValidatedPythonPath } from '../python-detector';
-import { getConfiguredPythonPath } from '../python-env-manager';
+import { getConfiguredPythonPath, pythonEnvManager } from '../python-env-manager';
+import { getAugmentedEnv } from '../env-utils';
 
 /**
  * Configuration manager for insights service
@@ -107,9 +108,15 @@ export class InsightsConfig {
   getProcessEnv(): Record<string, string> {
     const autoBuildEnv = this.loadAutoBuildEnv();
     const profileEnv = getProfileEnv();
+    // Get Python environment (PYTHONPATH for bundled packages like python-dotenv)
+    const pythonEnv = pythonEnvManager.getPythonEnv();
+    // Use getAugmentedEnv() to ensure common tool paths (claude, dotnet, etc.)
+    // are available even when app is launched from Finder/Dock
+    const augmentedEnv = getAugmentedEnv();
 
     return {
-      ...process.env as Record<string, string>,
+      ...augmentedEnv,
+      ...pythonEnv, // Include PYTHONPATH for bundled site-packages
       ...autoBuildEnv,
       ...profileEnv,
       PYTHONUNBUFFERED: '1',
diff --git a/apps/frontend/src/main/insights/insights-executor.ts b/apps/frontend/src/main/insights/insights-executor.ts
index d5565620..4cae6e4a 100644
--- a/apps/frontend/src/main/insights/insights-executor.ts
+++ b/apps/frontend/src/main/insights/insights-executor.ts
@@ -130,6 +130,7 @@ export class InsightsExecutor extends EventEmitter {
       let suggestedTask: InsightsChatMessage['suggestedTask'] | undefined;
       const toolsUsed: InsightsToolUsage[] = [];
       let allInsightsOutput = '';
+      let stderrOutput = '';
 
       proc.stdout?.on('data', (data: Buffer) => {
         const text = data.toString();
@@ -159,8 +160,9 @@ export class InsightsExecutor extends EventEmitter {
 
       proc.stderr?.on('data', (data: Buffer) => {
         const text = data.toString();
-        // Collect stderr for rate limit detection too
+        // Collect stderr for rate limit detection and error reporting
         allInsightsOutput = (allInsightsOutput + text).slice(-10000);
+        stderrOutput = (stderrOutput + text).slice(-2000);
         console.error('[Insights]', text);
       });
 
@@ -196,7 +198,11 @@ export class InsightsExecutor extends EventEmitter {
             toolsUsed
           });
         } else {
-          const error = `Process exited with code ${code}`;
+          // Include stderr output in error message for debugging
+          const stderrSummary = stderrOutput.trim()
+            ? `\n\nError output:\n${stderrOutput.slice(-500)}`
+            : '';
+          const error = `Process exited with code ${code}${stderrSummary}`;
           this.emit('stream-chunk', projectId, {
             type: 'error',
             error