Cannot import name 'WinDLL' from 'ctypes' in macOS

[TOAOQ]

Describe the bug

I cannot connect to bastion rdp on macOS.

Mac, PS, AZ Clie and Python all are up-to-date

Related command

az network bastion rdp --name "name" --resource-group "resource_group" --target-resource-id "target_resource_id" --enable-mfa --configure

Errors

The command failed with an unexpected error. Here is the traceback:
cannot import name 'WinDLL' from 'ctypes' (/opt/homebrew/Cellar/python@3.12/3.12.11/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)
Traceback (most recent call last):
File "/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/lib/python3.12/site-packages/knack/cli.py", line 233, in invoke
cmd_result = self.invocation.execute(args)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 666, in execute
raise ex
File "/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 734, in _run_jobs_serially
results.append(self._run_job(expanded_arg, cmd_copy))
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 703, in _run_job
result = cmd_copy(params)
^^^^^^^^^^^^^^^^
File "/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 336, in call
return self.handler(*args, **kwargs)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/command_operation.py", line 120, in handler
return op(**command_args)
^^^^^^^^^^^^^^^^^^
File "/Users/qtc/.azure/cliextensions/bastion/azext_bastion/custom.py", line 285, in rdp_bastion_host
from ._process_helper import launch_and_wait
File "/Users/qtc/.azure/cliextensions/bastion/azext_bastion/_process_helper.py", line 9, in
from ctypes import WinDLL, c_int, c_size_t, Structure, WinError, sizeof, pointer
ImportError: cannot import name 'WinDLL' from 'ctypes' (/opt/homebrew/Cellar/python@3.12/3.12.11/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)
To check existing issues, please visit: https://github.com/Azure/azure-cli/issues

Issue script & Debug output

Will provide upon request

Expected behavior

That an RDP session opens using installed macOS Windows App as do other .rdp files and commands

Environment Summary

azure-cli 2.74.0

core 2.74.0
telemetry 1.1.0

Extensions:
bastion 1.4.0

Dependencies:
msal 1.32.3
azure-mgmt-resource 23.3.0

Python location '/opt/homebrew/Cellar/azure-cli/2.74.0/libexec/bin/python'
Config directory '/Users/qtc/.azure'
Extensions directory '/Users/qtc/.azure/cliextensions'

Python (Darwin) 3.12.11 (main, Jun 3 2025, 15:41:47) [Clang 17.0.0 (clang-1700.0.13.3)]

Legal docs and information: aka.ms/AzureCliLegal

Your CLI is up-to-date.

Additional context

No response

[yonzhan]

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

[github-actions]

Here are some similar issues that might help you. Please check if they can solve your problem.

• cannot import name 'WinDLL' from 'ctypes' on macOS #31296
• az network bastion fails to connect #25391
• az network bastion rdp #26298
• bastion rdp using azure cli #23965
• Bastion RDP with native client #24736

---

Possible solution (Extracted from existing issue, might be incorrect; please verify carefully)

Please update your bastion extension by running the below command and that should fix this.

az extension update -n bastion

Hope this helps.

Reference:

• az network bastion fails to connect #25391 (comment)
• az network bastion fails to connect #25391 (comment)
• Bastion RDP with native client #24736 (comment)

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[microsoft-github-policy-service]

Thanks for the feedback! We are routing this to the appropriate team for follow-up. cc @isamorris, @bastionsuppgithub.

[microsoft-github-policy-service]

Thanks for the feedback! We are routing this to the appropriate team for follow-up. cc @isamorris, @bastionsuppgithub.

[TOAOQ]

I have looked in a lot of similar issues, on this site and elsewhere but didn't find any solution\

[TOAOQ]

Here are some similar issues that might help you. Please check if they can solve your problem.

• cannot import name 'WinDLL' from 'ctypes' on macOS #31296
• az network bastion fails to connect #25391
• az network bastion rdp #26298
• bastion rdp using azure cli #23965
• Bastion RDP with native client #24736

Possible solution (Extracted from existing issue, might be incorrect; please verify carefully)

Please update your bastion extension by running the below command and that should fix this.

az extension update -n bastion

Hope this helps.

Reference:

• az network bastion fails to connect #25391 (comment)
• az network bastion fails to connect #25391 (comment)
• Bastion RDP with native client #24736 (comment)

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az extension update -n bastion did something but not solve my issue