Pip failed with status code 3221225477 on install

**ENVIRONMENT**

Windows 10

az version:
{
"azure-cli": "2.69.0",
"azure-cli-core": "2.69.0",
"azure-cli-telemetry": "1.1.0",
"extensions": {}
}

pip 25.0.1

**ISSUE**

az extension add --name azure-iot:

An error occurred. Pip failed with status code 3221225477. Use --debug for more information.

**DEBUG INFO**

az extension add --name azure-iot --debug:

cli.knack.cli: Command arguments: ['extension', 'add', '--name', 'azure-iot', '--debug']
cli.knack.cli: __init__ debug log:
Enable color in terminal.
Enable VT mode.
cli.knack.cli: Event: Cli.PreExecute []
cli.knack.cli: Event: CommandParser.OnGlobalArgumentsCreate [, , ]
cli.knack.cli: Event: CommandInvoker.OnPreCommandTableCreate []
cli.azure.cli.core: Modules found from index for 'extension': ['azure.cli.command_modules.extension']
cli.azure.cli.core: Loading command modules:
cli.azure.cli.core: Name Load Time Groups Commands
cli.azure.cli.core: extension 0.012 1 7
cli.azure.cli.core: Total (1) 0.012 1 7
cli.azure.cli.core: Loaded 1 groups, 7 commands.
cli.azure.cli.core: Found a match in the command table.
cli.azure.cli.core: Raw command : extension add
cli.azure.cli.core: Command table: extension add
cli.knack.cli: Event: CommandInvoker.OnPreCommandTableTruncate []
cli.azure.cli.core.azlogging: metadata file logging enabled - writing logs to 'C:\Users\ITRACAS1\.azure\commands\2025-02-17.14-20-57.extension_add.28516.log'.
az_command_data_logger: command args: extension add --name {} --debug
cli.knack.cli: Event: CommandInvoker.OnPreArgumentLoad [.add_subscription_parameter at 0x0000013A708C31A0>]
cli.knack.cli: Event: CommandInvoker.OnPostArgumentLoad []
cli.knack.cli: Event: CommandInvoker.OnPostCommandTableCreate [.add_ids_arguments at 0x0000013A70941580>, .add_cache_arguments at 0x0000013A709416C0>, .update_breaking_change_info at 0x0000013A70941760>]
cli.knack.cli: Event: CommandInvoker.OnCommandTableLoaded []
cli.knack.cli: Event: CommandInvoker.OnPreParseArgs []
cli.knack.cli: Event: CommandInvoker.OnPostParseArgs [, , .parse_ids_arguments at 0x0000013A70941620>]
urllib3.connectionpool: Starting new HTTPS connection (1): aka.ms:443
urllib3.connectionpool: https://aka.ms:443 "GET /azure-cli-extension-index-v1 HTTP/1.1" 301 0
urllib3.connectionpool: Starting new HTTPS connection (1): azcliextensionsync.blob.core.windows.net:443
urllib3.connectionpool: https://azcliextensionsync.blob.core.windows.net:443 "GET /index1/index.json HTTP/1.1" 200 4911022
cli.azure.cli.core.extension._resolve: No preview versions need to be tried.
cli.azure.cli.core.extension._resolve: Candidates ['azure_iot-0.10.11-py3-none-any.whl', 'azure_iot-0.10.15-py3-none-any.whl', 'azure_iot-0.10.17-py3-none-any.whl', 'azure_iot-0.11.0-py3-none-any.whl', 'azure_iot-0.12.1-py3-none-any.whl', 'azure_iot-0.13.0-py3-none-any.whl', 'azure_iot-0.14.0-py3-none-any.whl', 'azure_iot-0.14.1-py3-none-any.whl', 'azure_iot-0.15.0-py3-none-any.whl', 'azure_iot-0.16.1-py3-none-any.whl', 'azure_iot-0.17.0-py3-none-any.whl', 'azure_iot-0.17.1-py3-none-any.whl', 'azure_iot-0.17.3-py3-none-any.whl', 'azure_iot-0.18.0-py3-none-any.whl', 'azure_iot-0.18.1-py3-none-any.whl', 'azure_iot-0.18.2-py3-none-any.whl', 'azure_iot-0.18.3-py3-none-any.whl', 'azure_iot-0.19.0-py3-none-any.whl', 'azure_iot-0.19.1-py3-none-any.whl', 'azure_iot-0.20.0-py3-none-any.whl', 'azure_iot-0.21.0-py3-none-any.whl', 'azure_iot-0.21.1-py3-none-any.whl', 'azure_iot-0.21.2-py3-none-any.whl', 'azure_iot-0.21.3-py3-none-any.whl', 'azure_iot-0.21.4-py3-none-any.whl', 'azure_iot-0.21.5-py3-none-any.whl', 'azure_iot-0.22.0-py3-none-any.whl', 'azure_iot-0.23.0-py3-none-any.whl', 'azure_iot-0.23.1-py3-none-any.whl', 'azure_iot-0.24.0-py3-none-any.whl', 'azure_iot-0.25.0-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['azure_iot-0.10.11-py3-none-any.whl', 'azure_iot-0.10.15-py3-none-any.whl', 'azure_iot-0.10.17-py3-none-any.whl', 'azure_iot-0.11.0-py3-none-any.whl', 'azure_iot-0.12.1-py3-none-any.whl', 'azure_iot-0.13.0-py3-none-any.whl', 'azure_iot-0.14.0-py3-none-any.whl', 'azure_iot-0.14.1-py3-none-any.whl', 'azure_iot-0.15.0-py3-none-any.whl', 'azure_iot-0.16.1-py3-none-any.whl', 'azure_iot-0.17.0-py3-none-any.whl', 'azure_iot-0.17.1-py3-none-any.whl', 'azure_iot-0.17.3-py3-none-any.whl', 'azure_iot-0.18.0-py3-none-any.whl', 'azure_iot-0.18.1-py3-none-any.whl', 'azure_iot-0.18.2-py3-none-any.whl', 'azure_iot-0.18.3-py3-none-any.whl', 'azure_iot-0.19.0-py3-none-any.whl', 'azure_iot-0.19.1-py3-none-any.whl', 'azure_iot-0.20.0-py3-none-any.whl', 'azure_iot-0.21.0-py3-none-any.whl', 'azure_iot-0.21.1-py3-none-any.whl', 'azure_iot-0.21.2-py3-none-any.whl', 'azure_iot-0.21.3-py3-none-any.whl', 'azure_iot-0.21.4-py3-none-any.whl', 'azure_iot-0.21.5-py3-none-any.whl', 'azure_iot-0.22.0-py3-none-any.whl', 'azure_iot-0.23.0-py3-none-any.whl', 'azure_iot-0.23.1-py3-none-any.whl', 'azure_iot-0.24.0-py3-none-any.whl', 'azure_iot-0.25.0-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['azure_iot-0.10.11-py3-none-any.whl', 'azure_iot-0.10.15-py3-none-any.whl', 'azure_iot-0.10.17-py3-none-any.whl', 'azure_iot-0.11.0-py3-none-any.whl', 'azure_iot-0.12.1-py3-none-any.whl', 'azure_iot-0.13.0-py3-none-any.whl', 'azure_iot-0.14.0-py3-none-any.whl', 'azure_iot-0.14.1-py3-none-any.whl', 'azure_iot-0.15.0-py3-none-any.whl', 'azure_iot-0.16.1-py3-none-any.whl', 'azure_iot-0.17.0-py3-none-any.whl', 'azure_iot-0.17.1-py3-none-any.whl', 'azure_iot-0.17.3-py3-none-any.whl', 'azure_iot-0.18.0-py3-none-any.whl', 'azure_iot-0.18.1-py3-none-any.whl', 'azure_iot-0.18.2-py3-none-any.whl', 'azure_iot-0.18.3-py3-none-any.whl', 'azure_iot-0.19.0-py3-none-any.whl', 'azure_iot-0.19.1-py3-none-any.whl', 'azure_iot-0.20.0-py3-none-any.whl', 'azure_iot-0.21.0-py3-none-any.whl', 'azure_iot-0.21.1-py3-none-any.whl', 'azure_iot-0.21.2-py3-none-any.whl', 'azure_iot-0.21.3-py3-none-any.whl', 'azure_iot-0.21.4-py3-none-any.whl', 'azure_iot-0.21.5-py3-none-any.whl', 'azure_iot-0.22.0-py3-none-any.whl', 'azure_iot-0.23.0-py3-none-any.whl', 'azure_iot-0.23.1-py3-none-any.whl', 'azure_iot-0.24.0-py3-none-any.whl', 'azure_iot-0.25.0-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['azure_iot-0.10.11-py3-none-any.whl', 'azure_iot-0.10.15-py3-none-any.whl', 'azure_iot-0.10.17-py3-none-any.whl', 'azure_iot-0.11.0-py3-none-any.whl', 'azure_iot-0.12.1-py3-none-any.whl', 'azure_iot-0.13.0-py3-none-any.whl', 'azure_iot-0.14.0-py3-none-any.whl', 'azure_iot-0.14.1-py3-none-any.whl', 'azure_iot-0.15.0-py3-none-any.whl', 'azure_iot-0.16.1-py3-none-any.whl', 'azure_iot-0.17.0-py3-none-any.whl', 'azure_iot-0.17.1-py3-none-any.whl', 'azure_iot-0.17.3-py3-none-any.whl', 'azure_iot-0.18.0-py3-none-any.whl', 'azure_iot-0.18.1-py3-none-any.whl', 'azure_iot-0.18.2-py3-none-any.whl', 'azure_iot-0.18.3-py3-none-any.whl', 'azure_iot-0.19.0-py3-none-any.whl', 'azure_iot-0.19.1-py3-none-any.whl', 'azure_iot-0.20.0-py3-none-any.whl', 'azure_iot-0.21.0-py3-none-any.whl', 'azure_iot-0.21.1-py3-none-any.whl', 'azure_iot-0.21.2-py3-none-any.whl', 'azure_iot-0.21.3-py3-none-any.whl', 'azure_iot-0.21.4-py3-none-any.whl', 'azure_iot-0.21.5-py3-none-any.whl', 'azure_iot-0.22.0-py3-none-any.whl', 'azure_iot-0.23.0-py3-none-any.whl', 'azure_iot-0.23.1-py3-none-any.whl', 'azure_iot-0.24.0-py3-none-any.whl', 'azure_iot-0.25.0-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['azure_iot-0.10.11-py3-none-any.whl', 'azure_iot-0.10.15-py3-none-any.whl', 'azure_iot-0.10.17-py3-none-any.whl', 'azure_iot-0.11.0-py3-none-any.whl', 'azure_iot-0.12.1-py3-none-any.whl', 'azure_iot-0.13.0-py3-none-any.whl', 'azure_iot-0.14.0-py3-none-any.whl', 'azure_iot-0.14.1-py3-none-any.whl', 'azure_iot-0.15.0-py3-none-any.whl', 'azure_iot-0.16.1-py3-none-any.whl', 'azure_iot-0.17.0-py3-none-any.whl', 'azure_iot-0.17.1-py3-none-any.whl', 'azure_iot-0.17.3-py3-none-any.whl', 'azure_iot-0.18.0-py3-none-any.whl', 'azure_iot-0.18.1-py3-none-any.whl', 'azure_iot-0.18.2-py3-none-any.whl', 'azure_iot-0.18.3-py3-none-any.whl', 'azure_iot-0.19.0-py3-none-any.whl', 'azure_iot-0.19.1-py3-none-any.whl', 'azure_iot-0.20.0-py3-none-any.whl', 'azure_iot-0.21.0-py3-none-any.whl', 'azure_iot-0.21.1-py3-none-any.whl', 'azure_iot-0.21.2-py3-none-any.whl', 'azure_iot-0.21.3-py3-none-any.whl', 'azure_iot-0.21.4-py3-none-any.whl', 'azure_iot-0.21.5-py3-none-any.whl', 'azure_iot-0.22.0-py3-none-any.whl', 'azure_iot-0.23.0-py3-none-any.whl', 'azure_iot-0.23.1-py3-none-any.whl', 'azure_iot-0.24.0-py3-none-any.whl', 'azure_iot-0.25.0-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Chosen {'downloadUrl': 'https://github.com/Azure/azure-iot-cli-extension/releases/download/v0.25.0/azure_iot-0.25.0-py3-none-any.whl', 'filename': 'azure_iot-0.25.0-py3-none-any.whl', 'metadata': {'azext.minCliCoreVersion': '2.46.0', 'classifiers': ['Development Status :: 4 - Beta', 'Intended Audience :: Developers', 'Intended Audience :: System Administrators', 'Programming Language :: Python', 'Programming Language :: Python :: 3 :: Only', 'Programming Language :: Python :: 3', 'Programming Language :: Python :: 3.8', 'Programming Language :: Python :: 3.9', 'Programming Language :: Python :: 3.10', 'License :: OSI Approved :: MIT License'], 'extensions': {'python.details': {'contacts': [{'email': 'iotupx@microsoft.com', 'name': 'Microsoft', 'role': 'author'}], 'document_names': {'description': 'DESCRIPTION.rst'}, 'project_urls': {'Home': 'https://github.com/azure/azure-iot-cli-extension'}}}, 'extras': ['uamqp'], 'generator': 'bdist_wheel (0.30.0)', 'license': 'MIT', 'license_file': 'LICENSE', 'metadata_version': '2.0', 'name': 'azure-iot', 'requires_python': '>=3.8', 'run_requires': [{'requires': ['azure-core (<2.0.0,>=1.24.0)', 'azure-identity (<2.0.0,>=1.6.1)', 'azure-iot-device (~=2.11)', 'azure-mgmt-core (<2.0.0,>=1.3.0)', 'azure-storage-blob (<13.0.0,>=12.14.0)', 'jsonschema (~=3.2.0)', 'msrest (>=0.6.21)', 'msrestazure (<2.0.0,>=0.6.3)', 'packaging', 'tomli (~=2.0)', 'tomli-w (~=1.0)', 'tqdm (~=4.62)', 'treelib (~=1.6)']}, {'extra': 'uamqp', 'requires': ['uamqp (<=1.6.8,>=1.2)']}], 'summary': 'The Azure IoT extension for Azure CLI.', 'version': '0.25.0'}, 'sha256Digest': '7db4bc07667efa8472513d9e121fb2551fcaeae68255c7bc0768ad4177c1b1c6'}
cli.azure.cli.core.extension.operations: Extension source is url? True
cli.azure.cli.core.extension.operations: Downloading https://github.com/Azure/azure-iot-cli-extension/releases/download/v0.25.0/azure_iot-0.25.0-py3-none-any.whl to C:\Users\ITRACAS1\AppData\Local\Temp\tmpsy5hrcky\azure_iot-0.25.0-py3-none-any.whl
urllib3.connectionpool: Starting new HTTPS connection (1): github.com:443
urllib3.connectionpool: https://github.com:443 "GET /Azure/azure-iot-cli-extension/releases/download/v0.25.0/azure_iot-0.25.0-py3-none-any.whl HTTP/1.1" 302 0
urllib3.connectionpool: Starting new HTTPS connection (1): objects.githubusercontent.com:443
urllib3.connectionpool: https://objects.githubusercontent.com:443 "GET /github-production-release-asset-2e65be/103456760/bb9289ae-670c-4ec4-83c2-12e127909614?X-Amz-Algorithm=AWS4-HMAC-SHA256&X-Amz-Credential=releaseassetproduction%2F20250217%2Fus-east-1%2Fs3%2Faws4_request&X-Amz-Date=20250217T131950Z&X-Amz-Expires=300&X-Amz-Signature=b61463f88818e169ebc45557ea98a89d240538a7f4ca2bf35c52b23a4eba027e&X-Amz-SignedHeaders=host&response-content-disposition=attachment%3B%20filename%3Dazure_iot-0.25.0-py3-none-any.whl&response-content-type=application%2Foctet-stream HTTP/1.1" 200 739656
cli.azure.cli.core.extension.operations: Downloaded to C:\Users\ITRACAS1\AppData\Local\Temp\tmpsy5hrcky\azure_iot-0.25.0-py3-none-any.whl
cli.azure.cli.core.extension.operations: Validating the extension C:\Users\ITRACAS1\AppData\Local\Temp\tmpsy5hrcky\azure_iot-0.25.0-py3-none-any.whl
cli.azure.cli.core.extension.operations: Checksum of C:\Users\ITRACAS1\AppData\Local\Temp\tmpsy5hrcky\azure_iot-0.25.0-py3-none-any.whl is OK
cli.azure.cli.core.extension.operations: Validation successful on C:\Users\ITRACAS1\AppData\Local\Temp\tmpsy5hrcky\azure_iot-0.25.0-py3-none-any.whl
cli.azure.cli.core.extension.operations: Executing pip with args: ['install', '--target', 'C:\\Users\\ITRACAS1\\.azure\\cliextensions\\azure-iot', 'C:\\Users\\ITRACAS1\\AppData\\Local\\Temp\\tmpsy5hrcky\\azure_iot-0.25.0-py3-none-any.whl']
cli.azure.cli.core.extension.operations: Running: ['C:\\Program Files\\Microsoft SDKs\\Azure\\CLI2\\python.exe', '-m', 'pip', 'install', '--target', 'C:\\Users\\ITRACAS1\\.azure\\cliextensions\\azure-iot', 'C:\\Users\\ITRACAS1\\AppData\\Local\\Temp\\tmpsy5hrcky\\azure_iot-0.25.0-py3-none-any.whl', '--disable-pip-version-check', '--no-cache-dir']
cli.azure.cli.core.extension.operations:
cli.azure.cli.core.extension.operations: Command '['C:\\Program Files\\Microsoft SDKs\\Azure\\CLI2\\python.exe', '-m', 'pip', 'install', '--target', 'C:\\Users\\ITRACAS1\\.azure\\cliextensions\\azure-iot', 'C:\\Users\\ITRACAS1\\AppData\\Local\\Temp\\tmpsy5hrcky\\azure_iot-0.25.0-py3-none-any.whl', '--disable-pip-version-check', '--no-cache-dir']' returned non-zero exit status 3221225477.
cli.azure.cli.core.extension.operations: Pip failed so deleting anything we might have installed at C:\Users\ITRACAS1\.azure\cliextensions\azure-iot
cli.azure.cli.core.azclierror: Traceback (most recent call last):
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\knack/cli.py", line 233, in invoke
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/commands/__init__.py", line 666, in execute
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/commands/__init__.py", line 734, in _run_jobs_serially
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/commands/__init__.py", line 703, in _run_job
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/commands/__init__.py", line 336, in __call__
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/commands/command_operation.py", line 120, in handler
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/command_modules/extension/custom.py", line 16, in add_extension_cmd
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/extension/operations.py", line 343, in add_extension
File "D:\a\_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/extension/operations.py", line 172, in _add_whl_ext
knack.util.CLIError: An error occurred. Pip failed with status code 3221225477. Use --debug for more information.

cli.azure.cli.core.azclierror: An error occurred. Pip failed with status code 3221225477. Use --debug for more information.
az_command_data_logger: An error occurred. Pip failed with status code 3221225477. Use --debug for more information.
cli.knack.cli: Event: Cli.PostExecute []
az_command_data_logger: exit code: 1
cli.__main__: Command ran in 10.988 seconds (init: 0.890, invoke: 10.098)
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 3867 in cache file under C:\Users\ITRACAS1\.azure\telemetry\20250217142108166
telemetry.main: Begin creating telemetry upload process.
telemetry.process: Creating upload process: "C:\Program Files\Microsoft SDKs\Azure\CLI2\python.exe C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\azure\cli\telemetry\__init__.pyc C:\Users\ITRACAS1\.azure C:\Users\ITRACAS1\.azure\telemetry\20250217142108166"
telemetry.process: Return from creating process 17440
telemetry.main: Finish creating telemetry upload process.

Start by reproducing `az extension add --name azure-iot --debug` on Windows 10 and inspect the generated command log at `C:\Users\ITRACAS1\.azure\commands\2025-02-17.14-20-57.extension_add.28516.log`. Trace the pip failure for the selected `azure_iot-0.25.0-py3-none-any.whl`; done means the extension installs successfully or the failure has an actionable diagnostic.

Written by the indexing model from the issue text.