Unable to add azure-devops extension in Azure CLI v2.56.0 on Windows: ImportError: DLL load failed while importing _ctypes: The specified module could not be found.

[MattNipper]

Describe the bug

With the current version of Azure CLI, I am unable to install the azure-devops extension on a Windows machine. This seems related to the python/pip packaged in CLI2.

Related command

az extension add --name bastion --debug

Errors

An error occurred. Pip failed with status code 1. Use --debug for more information.

Issue script & Debug output

Traceback (most recent call last):
File "", line 198, in _run_module_as_main
File "", line 88, in run_code
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_main.py", line 22, in
from pip._internal.cli.main import main as _main
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\main.py", line 10, in
from pip._internal.cli.autocompletion import autocomplete
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\autocompletion.py", line 10, in
from pip._internal.cli.main_parser import create_main_parser
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\main_parser.py", line 9, in
from pip._internal.build_env import get_runnable_pip
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\build_env.py", line 19, in
from pip._internal.cli.spinners import open_spinner
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\spinners.py", line 9, in
from pip._internal.utils.logging import get_indentation
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\utils\logging.py", line 29, in
from pip._internal.utils.misc import ensure_dir
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\utils\misc.py", line 44, in
from pip.internal.locations import get_major_minor_version
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\locations_init.py", line 14, in
from . import _sysconfig
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\locations_sysconfig.py", line 11, in
from .base import change_root, get_major_minor_version, is_osx_framework
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\locations\base.py", line 9, in
from pip._internal.utils import appdirs
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\utils\appdirs.py", line 13, in
from pip._vendor import platformdirs as appdirs
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\platformdirs_init.py", line 46, in
PlatformDirs = set_platform_dir_class() #: Currently active platform
^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\platformdirs_init.py", line 26, in _set_platform_dir_class
from pip.vendor.platformdirs.windows import Windows as Result
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\platformdirs\windows.py", line 4, in
import ctypes
File "ctypes_init.py", line 8, in
ImportError: DLL load failed while importing _ctypes: The specified module could not be found.

Expected behavior

The extension should be installed.

Environment Summary

azure-cli 2.56.0

core 2.56.0
telemetry 1.1.0

Extensions:
azure-batch-cli-extensions 7.0.0
bastion 0.2.5

Dependencies:
msal 1.24.0b2
azure-mgmt-resource 23.1.0b2

Additional context

No response

[azure-client-tools-bot-prd]

Hi @MattNipper
Find similar issue #23015.

Issue title	azure-cli-core: Test failures with conflicting subparsers in Python 3.11.0b3
Create time	2022-06-24
Comment number	10

---

Please confirm if this resolves your issue.

[yonzhan]

Thank you for opening this issue, we will look into it.

[jiasli]

I can't repo this issue on my machine as both ctypes and _ctypes can be imported correctly.

> & "C:\Program Files\Microsoft SDKs\Azure\CLI2\python.exe" -I -c "import ctypes; print(ctypes.__file__)"
C:\Program Files\Microsoft SDKs\Azure\CLI2\python311.zip\ctypes\__init__.pyc

> & "C:\Program Files\Microsoft SDKs\Azure\CLI2\python.exe" -I -c "import _ctypes; print(_ctypes.__file__)"
C:\Program Files\Microsoft SDKs\Azure\CLI2\_ctypes.pyd

Can you verify if C:\Program Files\Microsoft SDKs\Azure\CLI2\_ctypes.pyd exists?

> Get-Item "C:\Program Files\Microsoft SDKs\Azure\CLI2\_ctypes.pyd"

    Directory: C:\Program Files\Microsoft SDKs\Azure\CLI2

Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
-a---           12/4/2023  7:44 PM         124696 _ctypes.pyd

If not, I doubt the MSI installation is corrupted. Please try to perform a clean installation following #20990 and see if the error is gone.

[wpdonders]

I also face this issue (although on Azure CLI v2.58.0), and can confirm _ctypes.pyd exists on my machine. A clean installation does not fix the issue.

[jiasli]

@wpdonders, what is the output if you run the above commands?