diff --git a/src/utils/claude-detector.ts b/src/utils/claude-detector.ts
index 02d548c8..8649163a 100644
--- a/src/utils/claude-detector.ts
+++ b/src/utils/claude-detector.ts
@@ -3,6 +3,42 @@ import { execSync } from 'child_process';
 import { expandPath } from './helpers';
 import { ClaudeCliInfo } from '../types';
 
+/**
+ * Common Windows installation paths for Claude CLI native installer
+ * These are checked as fallback when 'where.exe claude' fails
+ */
+const WINDOWS_NATIVE_PATHS = [
+  // Native installer locations (Anthropic/Claude branded)
+  '%LOCALAPPDATA%\\Programs\\Claude\\claude.exe',
+  '%LOCALAPPDATA%\\AnthropicClaude\\claude.exe',
+  '%PROGRAMFILES%\\Claude\\claude.exe',
+  '%PROGRAMFILES%\\Anthropic\\Claude\\claude.exe',
+  // npm/bun global install locations (already in PATH, but check as fallback)
+  '%APPDATA%\\npm\\claude.cmd',
+  '%USERPROFILE%\\.bun\\bin\\claude.exe',
+];
+
+/**
+ * Expand Windows environment variables in path
+ */
+function expandWindowsPath(p: string): string {
+  return p.replace(/%([^%]+)%/g, (_, name) => process.env[name] || '');
+}
+
+/**
+ * Check common Windows installation paths for Claude CLI
+ * Returns the first valid path found, or null
+ */
+function findClaudeInWindowsPaths(): string | null {
+  for (const template of WINDOWS_NATIVE_PATHS) {
+    const expanded = expandWindowsPath(template);
+    if (fs.existsSync(expanded)) {
+      return expanded;
+    }
+  }
+  return null;
+}
+
 /**
  * Detect Claude CLI executable
  */
@@ -57,10 +93,19 @@ export function detectClaudeCli(): string | null {
     }
   } catch (_err) {
     // Command failed - claude not in PATH
-    // Fall through to return null
+    // Fall through to Windows fallback or return null
   }
 
-  // Priority 3: Claude not found
+  // Priority 3 (Windows only): Check common native installer locations
+  // This helps users who installed via Windows MSI/EXE but haven't run 'claude install'
+  if (isWindows) {
+    const nativePath = findClaudeInWindowsPaths();
+    if (nativePath) {
+      return nativePath;
+    }
+  }
+
+  // Priority 4: Claude not found
   return null;
 }
 
diff --git a/src/utils/error-manager.ts b/src/utils/error-manager.ts
index 65d364b8..6bd8626c 100644
--- a/src/utils/error-manager.ts
+++ b/src/utils/error-manager.ts
@@ -51,12 +51,25 @@ export class ErrorManager {
     console.error('  1. Install Claude CLI');
     console.error(`     ${color('https://docs.claude.com/install', 'path')}`);
     console.error('');
-    console.error('  2. Verify installation');
-    console.error(`     ${color('command -v claude', 'command')}   (Unix)`);
-    console.error(`     ${color('Get-Command claude', 'command')}  (Windows)`);
-    console.error('');
-    console.error('  3. Custom path (if installed elsewhere)');
-    console.error(`     ${color('export CCS_CLAUDE_PATH="/path/to/claude"', 'command')}`);
+
+    // Windows-specific guidance for native installer users
+    if (process.platform === 'win32') {
+      console.error('  2. If you used the Windows installer, run:');
+      console.error(`     ${color('claude install', 'command')}`);
+      console.error(dim('     This adds Claude to your PATH'));
+      console.error('');
+      console.error('  3. Verify installation');
+      console.error(`     ${color('Get-Command claude', 'command')}`);
+      console.error('');
+      console.error('  4. Custom path (if installed elsewhere)');
+      console.error(`     ${color('$env:CCS_CLAUDE_PATH="C:\\path\\to\\claude.exe"', 'command')}`);
+    } else {
+      console.error('  2. Verify installation');
+      console.error(`     ${color('command -v claude', 'command')}`);
+      console.error('');
+      console.error('  3. Custom path (if installed elsewhere)');
+      console.error(`     ${color('export CCS_CLAUDE_PATH="/path/to/claude"', 'command')}`);
+    }
     console.error('');
 
     this.showErrorCode(ERROR_CODES.CLAUDE_NOT_FOUND);