cannot import name 'WinDLL' from 'ctypes' on macOS

[tinfisterNP]

Describe the bug

I cannot connect to bastion rdp on macOS

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@3.12/3.12.10/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)
Traceback (most recent call last):
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 666, in execute
raise ex
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/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/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/command_operation.py", line 120, in handler
return op(**command_args)
^^^^^^^^^^^^^^^^^^
File "/Users/tinfister/.azure/cliextensions/bastion/azext_bastion/custom.py", line 285, in rdp_bastion_host
from ._process_helper import launch_and_wait
File "/Users/tinfister/.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@3.12/3.12.10/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)

Issue script & Debug output

cli.knack.cli: Command arguments: ['network', 'bastion', 'rdp', '--name', '', '--resource-group', '', '--target-resource-id', '', '--enable-mfa', '--configure', '--debug']
cli.knack.cli: init debug log:
Enable color in terminal.
cli.knack.cli: Event: Cli.PreExecute []
cli.knack.cli: Event: CommandParser.OnGlobalArgumentsCreate [<function CLILogging.on_global_arguments at 0x102d5b1a0>, <function OutputProducer.on_global_arguments at 0x102f28220>, <function CLIQuery.on_global_arguments at 0x102f4d9e0>]
cli.knack.cli: Event: CommandInvoker.OnPreCommandTableCreate []
cli.azure.cli.core: Modules found from index for 'network': ['azure.cli.command_modules.network', 'azure.cli.command_modules.privatedns', 'azext_bastion']
cli.azure.cli.core: Loading command modules:
cli.azure.cli.core: Name Load Time Groups Commands
cli.azure.cli.core: network 0.351 118 362
cli.azure.cli.core: privatedns 0.008 14 60
cli.azure.cli.core: Total (2) 0.360 132 422
cli.azure.cli.core: These extensions are not installed and will be skipped: ['azext_ai_examples', 'azext_next']
cli.azure.cli.core: Loading extensions:
cli.azure.cli.core: Name Load Time Groups Commands Directory
cli.azure.cli.core: bastion 0.004 2 9 /Users/tinfister/.azure/cliextensions/bastion
cli.azure.cli.core: Total (1) 0.004 2 9
cli.azure.cli.core: Loaded 132 groups, 431 commands.
cli.azure.cli.core: Found a match in the command table.
cli.azure.cli.core: Raw command : network bastion rdp
cli.azure.cli.core: Command table: network bastion rdp
cli.knack.cli: Event: CommandInvoker.OnPreCommandTableTruncate [<function AzCliLogging.init_command_file_logging at 0x1043bfce0>]
cli.azure.cli.core.azlogging: metadata file logging enabled - writing logs to '/Users/tinfister/.azure/commands/2025-04-18.11-07-20.network_bastion_rdp.8184.log'.
az_command_data_logger: command args: network bastion rdp --name {} --resource-group {} --target-resource-id {} --enable-mfa --configure --debug
cli.knack.cli: Event: CommandInvoker.OnPreArgumentLoad [<function register_global_subscription_argument..add_subscription_parameter at 0x10440c9a0>]
cli.knack.cli: Event: CommandInvoker.OnPostArgumentLoad []
cli.knack.cli: Event: CommandInvoker.OnPostCommandTableCreate [<function register_ids_argument..add_ids_arguments at 0x10440f240>, <function register_cache_arguments..add_cache_arguments at 0x10440f380>, <function register_upcoming_breaking_change_info..update_breaking_change_info at 0x10440f420>]
cli.knack.cli: Event: CommandInvoker.OnCommandTableLoaded []
cli.knack.cli: Event: CommandInvoker.OnPreParseArgs []
cli.knack.cli: Event: CommandInvoker.OnPostParseArgs [<function OutputProducer.handle_output_argument at 0x102f282c0>, <function CLIQuery.handle_query_parameter at 0x102f4da80>, <function register_ids_argument..parse_ids_arguments at 0x10440f2e0>]
az_command_data_logger: extension name: bastion
az_command_data_logger: extension version: 1.4.0
cli.azure.cli.core.azclierror: Traceback (most recent call last):
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 666, in execute
raise ex
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/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/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/command_operation.py", line 120, in handler
return op(**command_args)
^^^^^^^^^^^^^^^^^^
File "/Users/tinfister/.azure/cliextensions/bastion/azext_bastion/custom.py", line 285, in rdp_bastion_host
from ._process_helper import launch_and_wait
File "/Users/tinfister/.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@3.12/3.12.10/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)

cli.azure.cli.core.azclierror: The command failed with an unexpected error. Here is the traceback:
az_command_data_logger: The command failed with an unexpected error. Here is the traceback:
cli.azure.cli.core.azclierror: cannot import name 'WinDLL' from 'ctypes' (/opt/homebrew/Cellar/python@3.12/3.12.10/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)
Traceback (most recent call last):
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 666, in execute
raise ex
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/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/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/command_operation.py", line 120, in handler
return op(**command_args)
^^^^^^^^^^^^^^^^^^
File "/Users/tinfister/.azure/cliextensions/bastion/azext_bastion/custom.py", line 285, in rdp_bastion_host
from ._process_helper import launch_and_wait
File "/Users/tinfister/.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@3.12/3.12.10/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)
az_command_data_logger: cannot import name 'WinDLL' from 'ctypes' (/opt/homebrew/Cellar/python@3.12/3.12.10/Frameworks/Python.framework/Versions/3.12/lib/python3.12/ctypes/init.py)
Traceback (most recent call last):
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/init.py", line 666, in execute
raise ex
File "/opt/homebrew/Cellar/azure-cli/2.71.0/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/2.71.0/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/2.71.0/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/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/core/commands/command_operation.py", line 120, in handler
return op(**command_args)
^^^^^^^^^^^^^^^^^^
File "/Users/tinfister/.azure/cliextensions/bastion/azext_bastion/custom.py", line 285, in rdp_bastion_host
from ._process_helper import launch_and_wait
File "/Users/tinfister/.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@3.12/3.12.10/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
cli.knack.cli: Event: Cli.PostExecute [<function AzCliLogging.deinit_cmd_metadata_logging at 0x1043bff60>]
az_command_data_logger: exit code: 1
cli.main: Command ran in 0.530 seconds (init: 0.116, invoke: 0.414)
telemetry.main: Begin splitting cli events and extra events, total events: 1
telemetry.client: Accumulated 0 events. Flush the clients.
telemetry.main: Finish splitting cli events and extra events, cli events: 1
telemetry.save: Save telemetry record of length 8388 in cache file under /Users/tinfister/.azure/telemetry/20250418110720153
telemetry.main: Begin creating telemetry upload process.
telemetry.process: Creating upload process: "/opt/homebrew/Cellar/azure-cli/2.71.0/libexec/bin/python /opt/homebrew/Cellar/azure-cli/2.71.0/libexec/lib/python3.12/site-packages/azure/cli/telemetry/init.py /Users/tinfister/.azure /Users/tinfister/.azure/telemetry/20250418110720153"
telemetry.process: Return from creating process 8189
telemetry.main: Finish creating telemetry upload process.

Expected behavior

I expect it to work and connect to rdp

Environment Summary

azure-cli 2.71.0

core 2.71.0
telemetry 1.1.0

Extensions:
bastion 1.4.0

Dependencies:
msal 1.31.2b1
azure-mgmt-resource 23.1.1

Python location '/opt/homebrew/Cellar/azure-cli/2.71.0/libexec/bin/python'
Config directory '/Users/tinfister/.azure'
Extensions directory '/Users/tinfister/.azure/cliextensions'

Python (Darwin) 3.12.10 (main, Apr 8 2025, 11:35:47) [Clang 16.0.0 (clang-1600.0.26.6)]

Legal docs and information: aka.ms/AzureCliLegal

Your CLI is up-to-date.

Additional context

Installed azure cli from https://learn.microsoft.com/en-us/cli/azure/install-azure-cli-macos

[yonzhan]

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

[microsoft-github-policy-service]

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

[github-actions]

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

• https://learn.microsoft.com/en-us/azure/bastion/vm-upload-download-native doesn't work on macOS #28647
• az network bastion rdp error following docs #23228
• bastion rdp using azure cli #23965
• Windows RDP via Bastian using AZ network CLI from Mac won't work #27981
• az network bastion fails to connect #25391

---

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

Update your bastion extension by running the command az extension update -n bastion. This should fix the issue.

Reference:

• az network bastion fails to connect #25391 (comment)
• az network bastion fails to connect #25391 (comment)

Powered by issue-sentinel

[microsoft-github-policy-service]

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

[TOAOQ]

Describe the bug

I cannot connect to bastion rdp on macOS

Related command

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

Just installed azure-cli sing brew on my mac. OS, PWSH etc all are latest possible general release versions (no beta's) and encountered the same issue:

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/---/.azure'
Extensions directory '/Users/---/.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

Output from connection attempt:

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

[bebound]

Duplicate of #25151

This extension should provide a better error message for unsupported platform.