fix(windows): ensure pywin32 is bundled in Windows binary (ACS-306) (#1197)

* fix(spec): resolve circular import between spec.pipeline and core.client

Implement two-part fix to break circular import dependency:

1. Add __getattr__ lazy imports in spec/__init__.py to defer imports of
   SpecOrchestrator and get_specs_dir until accessed.

2. Move create_client import inside run_agent() method in
   spec/pipeline/agent_runner.py to avoid top-level import.

The circular import chain:
  spec.pipeline.agent_runner -> core.client -> agents.tools_pkg ->
  spec.validate_pkg.auto_fix -> spec.pipeline

By deferring both the pipeline imports in spec/__init__.py AND the
create_client import in agent_runner.py, the circular dependency
is broken.

The __getattr__ implementation caches imports in globals() for efficiency.

Refs: ACS-302

* fix(windows): ensure pywin32 is bundled in Windows binary (ACS-306)

Fixes ModuleNotFoundError: No module named 'win32api' when the MCP
library attempts to import Windows-specific utilities in packaged apps.

Root cause: The build script's critical packages validation did not
include pywin32 for Windows, causing cached bundles without pywin32
to be accepted during Windows binary builds.

Changes:
- Add pywin32 to critical packages validation on Windows
  (download-python.cjs, python-env-manager.ts)
- Remove Python version constraint from pywin32 dependency
  The MCP library unconditionally imports win32api on Windows
  regardless of Python version
- Validate pywin32 on all Python versions on Windows in
  dependency_validator.py (was 3.12+ only)
- Update error message to mention MCP library requirement
- Update tests to reflect new behavior

Refs: ACS-306

---------

Co-authored-by: StillKnotKnown <stillknotknown@users.noreply.github.com>

apps/backend/core/dependency_validator.py

@@ -18,7 +18,9 @@ def validate_platform_dependencies() -> None:
                    with helpful installation instructions.
     """
     # Check Windows-specific dependencies
-    if sys.platform == "win32" and sys.version_info >= (3, 12):
+    # pywin32 is required on all Python versions on Windows (ACS-306)
+    # The MCP library unconditionally imports win32api on Windows
+    if sys.platform == "win32":
         try:
             import pywintypes  # noqa: F401
         except ImportError:
@@ -29,13 +31,19 @@ def _exit_with_pywin32_error() -> None:
     """Exit with helpful error message for missing pywin32."""
     # Use sys.prefix to detect the virtual environment path
     # This works for venv and poetry environments
-    venv_activate = Path(sys.prefix) / "Scripts" / "activate"
+    # Check for common Windows activation scripts (activate, activate.bat, Activate.ps1)
+    scripts_dir = Path(sys.prefix) / "Scripts"
+    activation_candidates = [
+        scripts_dir / "activate",
+        scripts_dir / "activate.bat",
+        scripts_dir / "Activate.ps1",
+    ]
+    venv_activate = next((p for p in activation_candidates if p.exists()), None)
 
-    sys.exit(
-        "Error: Required Windows dependency 'pywin32' is not installed.\n"
-        "\n"
-        "Auto Claude requires pywin32 on Windows for LadybugDB/Graphiti memory integration.\n"
-        "\n"
+    # Build activation step only if activate script exists
+    activation_step = ""
+    if venv_activate:
+        activation_step = (
             "To fix this:\n"
             "1. Activate your virtual environment:\n"
             f"   {venv_activate}\n"
@@ -45,6 +53,26 @@ def _exit_with_pywin32_error() -> None:
             "\n"
             "   Or reinstall all dependencies:\n"
             "   pip install -r requirements.txt\n"
+        )
+    else:
+        # For system Python or environments without activate script
+        activation_step = (
+            "To fix this:\n"
+            "Install pywin32:\n"
+            "   pip install pywin32>=306\n"
+            "\n"
+            "   Or reinstall all dependencies:\n"
+            "   pip install -r requirements.txt\n"
+        )
+
+    sys.exit(
+        "Error: Required Windows dependency 'pywin32' is not installed.\n"
+        "\n"
+        "Auto Claude requires pywin32 on Windows for:\n"
+        "  - MCP library (win32api, win32con, win32job modules)\n"
+        "  - LadybugDB/Graphiti memory integration\n"
+        "\n"
+        f"{activation_step}"
         "\n"
         f"Current Python: {sys.executable}\n"
     )

apps/backend/requirements.txt

@@ -17,7 +17,8 @@ graphiti-core>=0.5.0; python_version >= "3.12"
 
 # Windows-specific dependency for LadybugDB/Graphiti
 # pywin32 provides Windows system bindings required by real_ladybug
-pywin32>=306; sys_platform == "win32" and python_version >= "3.12"
+# Required on all Python versions on Windows (ACS-306) - MCP library unconditionally imports win32api
+pywin32>=306; sys_platform == "win32"
 
 # Google AI (optional - for Gemini LLM and embeddings)
 google-generativeai>=0.8.0

apps/backend/spec/pipeline/agent_runner.py

@@ -12,7 +12,6 @@ from ui.capabilities import configure_safe_encoding
 
 configure_safe_encoding()
 
-from core.client import create_client
 from debug import debug, debug_detailed, debug_error, debug_section, debug_success
 from security.tool_input_validator import get_safe_tool_input
 from task_logger import (
@@ -21,6 +20,10 @@ from task_logger import (
     TaskLogger,
 )
 
+# Lazy import create_client to avoid circular import with core.client
+# The import chain: spec.pipeline -> agent_runner -> core.client -> agents.tools_pkg -> spec.validate_pkg
+# By deferring the import, we break the circular dependency.
+
 
 class AgentRunner:
     """Manages agent execution with logging and error handling."""
@@ -116,6 +119,9 @@ class AgentRunner:
             "Creating Claude SDK client...",
             thinking_budget=thinking_budget,
         )
+        # Lazy import to avoid circular import with core.client
+        from core.client import create_client
+
         client = create_client(
             self.project_dir,
             self.spec_dir,

apps/frontend/scripts/download-python.cjs

@@ -709,12 +709,18 @@ async function downloadPython(targetPlatform, targetArch, options = {}) {
       // Without this check, corrupted caches with missing packages would be accepted
       // Note: Same list exists in python-env-manager.ts - keep them in sync
       // This validation assumes traditional Python packages with __init__.py (not PEP 420 namespace packages)
-      const criticalPackages = ['claude_agent_sdk', 'dotenv', 'pydantic_core'];
+      // pywin32 is platform-critical for Windows (ACS-306) - required by MCP library
+      // Note: We check for 'pywintypes' instead of 'pywin32' because pywin32 installs
+      // top-level modules (pywintypes, win32api, win32con, win32com) without a pywin32/__init__.py
+      const criticalPackages = ['claude_agent_sdk', 'dotenv', 'pydantic_core']
+        .concat(info.nodePlatform === 'win32' ? ['pywintypes'] : []);
       const missingPackages = criticalPackages.filter(pkg => {
         const pkgPath = path.join(sitePackagesDir, pkg);
-        // Check both directory and __init__.py for more robust validation
         const initFile = path.join(pkgPath, '__init__.py');
-        return !fs.existsSync(pkgPath) || !fs.existsSync(initFile);
+        // For single-file modules (like pywintypes.py), check for the file directly
+        const moduleFile = path.join(sitePackagesDir, pkg + '.py');
+        // Package is valid if directory+__init__.py exists OR single-file module exists
+        return !fs.existsSync(initFile) && !fs.existsSync(moduleFile);
       });
 
       if (missingPackages.length > 0) {
@@ -812,11 +818,18 @@ async function downloadPython(targetPlatform, targetArch, options = {}) {
       // Verify critical packages were installed before creating marker (fixes #416)
       // Note: Same list exists in python-env-manager.ts - keep them in sync
       // This validation assumes traditional Python packages with __init__.py (not PEP 420 namespace packages)
-      const criticalPackages = ['claude_agent_sdk', 'dotenv', 'pydantic_core'];
+      // pywin32 is platform-critical for Windows (ACS-306) - required by MCP library
+      // Note: We check for 'pywintypes' instead of 'pywin32' because pywin32 installs
+      // top-level modules (pywintypes, win32api, win32con, win32com) without a pywin32/__init__.py
+      const criticalPackages = ['claude_agent_sdk', 'dotenv', 'pydantic_core']
+        .concat(info.nodePlatform === 'win32' ? ['pywintypes'] : []);
       const postInstallMissing = criticalPackages.filter(pkg => {
         const pkgPath = path.join(sitePackagesDir, pkg);
         const initFile = path.join(pkgPath, '__init__.py');
-        return !fs.existsSync(pkgPath) || !fs.existsSync(initFile);
+        // For single-file modules (like pywintypes.py), check for the file directly
+        const moduleFile = path.join(sitePackagesDir, pkg + '.py');
+        // Package is valid if directory+__init__.py exists OR single-file module exists
+        return !fs.existsSync(initFile) && !fs.existsSync(moduleFile);
       });
 
       if (postInstallMissing.length > 0) {

apps/frontend/src/main/python-env-manager.ts

@@ -4,6 +4,7 @@ import path from 'path';
 import { EventEmitter } from 'events';
 import { app } from 'electron';
 import { findPythonCommand, getBundledPythonPath } from './python-detector';
+import { isWindows } from './platform';
 
 export interface PythonEnvStatus {
   ready: boolean;
@@ -67,7 +68,7 @@ export class PythonEnvManager extends EventEmitter {
     if (!venvPath) return null;
 
     const venvPython =
-      process.platform === 'win32'
+      isWindows()
         ? path.join(venvPath, 'Scripts', 'python.exe')
         : path.join(venvPath, 'bin', 'python');
 
@@ -126,14 +127,22 @@ export class PythonEnvManager extends EventEmitter {
     // This fixes GitHub issue #416 where marker exists but packages are missing
     // Note: Same list exists in download-python.cjs - keep them in sync
     // This validation assumes traditional Python packages with __init__.py (not PEP 420 namespace packages)
-    const criticalPackages = ['claude_agent_sdk', 'dotenv', 'pydantic_core'];
+    // pywin32 is platform-critical for Windows (ACS-306) - required by MCP library
+    // Note: We check for 'pywintypes' instead of 'pywin32' because pywin32 installs
+    // top-level modules (pywintypes, win32api, win32con, win32com) without a pywin32/__init__.py
+    const criticalPackages = ['claude_agent_sdk', 'dotenv', 'pydantic_core']
+      .concat(isWindows() ? ['pywintypes'] : []);
 
-    // Check each package exists with valid structure (directory + __init__.py)
+    // Check each package exists with valid structure
+    // For traditional packages: directory + __init__.py
+    // For single-file modules (like pywintypes.py): just the .py file
     const missingPackages = criticalPackages.filter((pkg) => {
       const pkgPath = path.join(sitePackagesPath, pkg);
       const initPath = path.join(pkgPath, '__init__.py');
-      // Package is valid if directory and __init__.py both exist
-      return !existsSync(pkgPath) || !existsSync(initPath);
+      // For single-file modules (like pywintypes.py), check for the file directly
+      const moduleFile = path.join(sitePackagesPath, `${pkg}.py`);
+      // Package is valid if directory+__init__.py exists OR single-file module exists
+      return !existsSync(initPath) && !existsSync(moduleFile);
     });
 
     // Log missing packages for debugging
@@ -551,7 +560,7 @@ if sys.version_info >= (3, 12):
       // For venv, site-packages is inside the venv
       const venvBase = this.getVenvBasePath();
       if (venvBase) {
-        if (process.platform === 'win32') {
+        if (isWindows()) {
           // Windows venv structure: Lib/site-packages (no python version subfolder)
           this.sitePackagesPath = path.join(venvBase, 'Lib', 'site-packages');
         } else {

tests/test_dependency_validator.py

@@ -4,10 +4,9 @@ Tests for dependency_validator module.
 
 Tests cover:
 - Platform-specific dependency validation
-- pywin32 validation on Windows Python 3.12+
+- pywin32 validation on Windows (all Python versions, ACS-306)
 - Helpful error messages for missing dependencies
 - No validation on non-Windows platforms
-- No validation on Python < 3.12
 """
 
 import sys
@@ -76,17 +75,32 @@ class TestValidatePlatformDependencies:
             # Should not raise SystemExit
             validate_platform_dependencies()
 
-    def test_windows_python_311_skips_validation(self):
-        """Windows + Python < 3.12 should skip pywin32 validation."""
+    def test_windows_python_311_validates_pywin32(self):
+        """
+        Windows + Python 3.11 should validate pywin32 (ACS-306).
+
+        Previously, validation only happened on Python 3.12+, but the MCP
+        library requires pywin32 on all Python versions on Windows.
+        """
+        import builtins
+
         with patch("sys.platform", "win32"), \
              patch("sys.version_info", (3, 11, 0)), \
-             patch("builtins.__import__") as mock_import:
-            # Even if pywintypes is not available, should not exit
-            mock_import.side_effect = ImportError("No module named 'pywintypes'")
+             patch("core.dependency_validator._exit_with_pywin32_error") as mock_exit:
 
-            # Should not raise SystemExit
+            original_import = builtins.__import__
+
+            def mock_import(name, *args, **kwargs):
+                if name == "pywintypes":
+                    raise ImportError("No module named 'pywintypes'")
+                return original_import(name, *args, **kwargs)
+
+            with patch("builtins.__import__", side_effect=mock_import):
                 validate_platform_dependencies()
 
+            # Should have called the error exit function (changed from skipping)
+            mock_exit.assert_called_once()
+
     def test_linux_skips_validation(self):
         """Non-Windows platforms should skip pywin32 validation."""
         with patch("sys.platform", "linux"), \
@@ -130,16 +144,32 @@ class TestValidatePlatformDependencies:
             # Should have called the error exit function
             mock_exit.assert_called_once()
 
-    def test_windows_python_310_skips_validation(self):
-        """Windows + Python 3.10 should skip pywin32 validation."""
+    def test_windows_python_310_validates_pywin32(self):
+        """
+        Windows + Python 3.10 should validate pywin32 (ACS-306).
+
+        Previously, validation only happened on Python 3.12+, but the MCP
+        library requires pywin32 on all Python versions on Windows.
+        """
+        import builtins
+
         with patch("sys.platform", "win32"), \
              patch("sys.version_info", (3, 10, 0)), \
-             patch("builtins.__import__") as mock_import:
-            mock_import.side_effect = ImportError("No module named 'pywintypes'")
+             patch("core.dependency_validator._exit_with_pywin32_error") as mock_exit:
 
-            # Should not raise SystemExit
+            original_import = builtins.__import__
+
+            def mock_import(name, *args, **kwargs):
+                if name == "pywintypes":
+                    raise ImportError("No module named 'pywintypes'")
+                return original_import(name, *args, **kwargs)
+
+            with patch("builtins.__import__", side_effect=mock_import):
                 validate_platform_dependencies()
 
+            # Should have called the error exit function (changed from skipping)
+            mock_exit.assert_called_once()
+
 
 # =============================================================================
 # TESTS FOR _exit_with_pywin32_error
@@ -150,7 +180,7 @@ class TestExitWithPywin32Error:
     """Tests for _exit_with_pywin32_error function."""
 
     def test_exit_message_contains_helpful_instructions(self):
-        """Error message should include installation instructions."""
+        """Error message should include installation instructions and mention MCP library."""
         with patch("sys.exit") as mock_exit:
             _exit_with_pywin32_error()
 
@@ -163,11 +193,15 @@ class TestExitWithPywin32Error:
             assert "pip install" in message.lower()
             assert "windows" in message.lower()
             assert "python" in message.lower()
+            # Should mention MCP library (ACS-306)
+            assert "mcp" in message.lower()
 
     def test_exit_message_contains_venv_path(self):
-        """Error message should include the virtual environment path."""
+        """Error message should include the virtual environment path when activate script exists."""
+        # Mock existsSync to return True for the activate script path
         with patch("sys.exit") as mock_exit, \
-             patch("sys.prefix", "/path/to/venv"):
+             patch("sys.prefix", "/path/to/venv"), \
+             patch("pathlib.Path.exists", return_value=True):
 
             _exit_with_pywin32_error()
 
@@ -182,6 +216,29 @@ class TestExitWithPywin32Error:
             assert expected_path in message or "/path/to/venv" in message
             assert "Scripts" in message
 
+    def test_exit_message_without_venv_activate(self):
+        """Error message should not include venv path when activate script doesn't exist."""
+        # Mock existsSync to return False (simulate system Python or missing activate)
+        # Also mock Path.exists to make the test deterministic
+        with patch("sys.exit") as mock_exit, \
+             patch("sys.prefix", "/usr"), \
+             patch("pathlib.Path.exists", return_value=False):
+
+            _exit_with_pywin32_error()
+
+            # Get the message passed to sys.exit
+            call_args = mock_exit.call_args[0][0]
+            message = str(call_args)
+
+            # Should NOT reference Scripts/activate when it doesn't exist
+            # Note: "Scripts" may appear in sys.executable path, so check specifically for activate references
+            assert "Scripts/activate" not in message and "Scripts\\activate" not in message
+            # Also check that "1. Activate your virtual environment" step is not present
+            assert "Activate your virtual environment" not in message
+            # Should still show installation instructions
+            assert "pip install" in message
+            assert "pywin32" in message
+
     def test_exit_message_contains_python_executable(self):
         """Error message should include the current Python executable."""
         with patch("sys.exit") as mock_exit, \