Installing extension fails if the env var PIP_REQUIRE_VIRTUALENV=true is set #32914
Description
Describe the bug
The env var PIP_REQUIRE_VIRTUALENV=true is read by pip to prevent unintentional installation of Python packages outside of an activated virtualenv (see also the official pip docs). Some consider it a best practice to their it in your .bash_profile or .bashrc file.
Unfortunately, it seems that, when the PIP_REQUIRE_VIRTUALENV=true env var is set, the az CLI fails to install extensions.
# Ensure the extension is not installed
az extension remove --name azure-devops
# Set the env var and attempt to install the extension
export PIP_REQUIRE_VIRTUALENV=true
# Try to install an extension
az extension add --name azure-devopsIf I manually unset the env var before running az, the issue can be worked around:
unset PIP_REQUIRE_VIRTUALENV
az extension add --name azure-devopsRelated command
az extension remove --name azure-devops
export PIP_REQUIRE_VIRTUALENV=true
az extension add --name azure-devops
Errors
An error occurred. Pip failed with status code 3. Use --debug for more information.
Issue script & Debug output
DEBUG: cli.knack.cli: Command arguments: ['extension', 'add', '--name', 'azure-devops', '--debug']
DEBUG: cli.knack.cli: __init__ debug log:
Cannot enable color.
DEBUG: cli.knack.cli: Event: Cli.PreExecute []
DEBUG: cli.knack.cli: Event: CommandParser.OnGlobalArgumentsCreate [<function CLILogging.on_global_arguments at 0x7bb0925327a0>, <function OutputProducer.on_global_arguments at 0x7bb092276660>, <function CLIQuery.on_global_arguments at 0x7bb0922ac7c0>]
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPreCommandTableCreate []
DEBUG: cli.azure.cli.core: Command index version or cloud profile is invalid or doesn't match the current command.
DEBUG: cli.azure.cli.core: Command index has been invalidated.
DEBUG: cli.azure.cli.core: No module found from index for '['extension', 'add', '--name', 'azure-devops', '--debug']'
DEBUG: cli.azure.cli.core: Loading all modules and extensions
DEBUG: cli.azure.cli.core: Discovered command modules: ['acr', 'acs', 'advisor', 'ams', 'apim', 'appconfig', 'appservice', 'aro', 'backup', 'batch', 'batchai', 'billing', 'botservice', 'cdn', 'cloud', 'cognitiveservices', 'compute_recommender', 'computefleet', 'config', 'configure', 'consumption', 'container', 'containerapp', 'cosmosdb', 'databoxedge', 'dls', 'dms', 'eventgrid', 'eventhubs', 'extension', 'feedback', 'find', 'hdinsight', 'identity', 'interactive', 'iot', 'keyvault', 'lab', 'managedservices', 'maps', 'marketplaceordering', 'monitor', 'mysql', 'netappfiles', 'network', 'policyinsights', 'postgresql', 'privatedns', 'profile', 'rdbms', 'redis', 'relay', 'resource', 'role', 'search', 'security', 'servicebus', 'serviceconnector', 'servicefabric', 'signalr', 'sql', 'sqlvm', 'storage', 'synapse', 'util', 'vm']
DEBUG: cli.azure.cli.core: Loading command modules...
DEBUG: cli.azure.cli.core: Loaded command modules in parallel:
DEBUG: cli.azure.cli.core: Name Load Time Groups Commands
DEBUG: cli.azure.cli.core: advisor 0.010 3 6
DEBUG: cli.azure.cli.core: ams 0.013 22 100
DEBUG: cli.azure.cli.core: appconfig 0.010 9 47
DEBUG: cli.azure.cli.core: apim 0.025 14 69
DEBUG: cli.azure.cli.core: acr 0.155 36 149
DEBUG: cli.azure.cli.core: aro 0.124 1 10
DEBUG: cli.azure.cli.core: backup 0.014 17 65
DEBUG: cli.azure.cli.core: batchai 0.006 10 30
DEBUG: cli.azure.cli.core: batch 0.079 32 96
DEBUG: cli.azure.cli.core: botservice 0.007 12 42
DEBUG: cli.azure.cli.core: appservice 0.230 88 299
DEBUG: cli.azure.cli.core: cloud 0.007 1 7
DEBUG: cli.azure.cli.core: billing 0.092 19 52
DEBUG: cli.azure.cli.core: cognitiveservices 0.010 15 59
DEBUG: cli.azure.cli.core: compute_recommender 0.027 1 1
DEBUG: cli.azure.cli.core: computefleet 0.025 1 1
DEBUG: cli.azure.cli.core: config 0.005 2 7
DEBUG: cli.azure.cli.core: configure 0.005 2 5
DEBUG: cli.azure.cli.core: container 0.036 2 17
DEBUG: cli.azure.cli.core: acs 0.358 18 96
DEBUG: cli.azure.cli.core: consumption 0.061 8 9
DEBUG: cli.azure.cli.core: cosmosdb 0.030 61 213
DEBUG: cli.azure.cli.core: databoxedge 0.033 2 2
DEBUG: cli.azure.cli.core: dls 0.009 6 36
DEBUG: cli.azure.cli.core: dms 0.006 3 22
DEBUG: cli.azure.cli.core: eventgrid 0.006 25 96
DEBUG: cli.azure.cli.core: extension 0.005 1 7
DEBUG: cli.azure.cli.core: feedback 0.004 1 2
DEBUG: cli.azure.cli.core: find 0.003 1 1
DEBUG: cli.azure.cli.core: hdinsight 0.040 10 45
DEBUG: cli.azure.cli.core: eventhubs 0.074 13 20
DEBUG: cli.azure.cli.core: interactive 0.001 1 1
DEBUG: cli.azure.cli.core: identity 0.037 2 8
DEBUG: cli.azure.cli.core: keyvault 0.016 20 114
DEBUG: cli.azure.cli.core: lab 0.136 9 30
DEBUG: cli.azure.cli.core: iot 0.200 18 81
DEBUG: cli.azure.cli.core: maps 0.005 4 8
DEBUG: cli.azure.cli.core: containerapp 0.353 39 132
DEBUG: cli.azure.cli.core: managedservices 0.050 3 8
DEBUG: cli.azure.cli.core: marketplaceordering 0.016 1 2
DEBUG: cli.azure.cli.core: cdn 0.492 8 50
DEBUG: cli.azure.cli.core: netappfiles 0.156 8 15
DEBUG: cli.azure.cli.core: mysql 0.171 16 57
DEBUG: cli.azure.cli.core: policyinsights 0.067 9 17
DEBUG: cli.azure.cli.core: postgresql 0.101 20 88
DEBUG: cli.azure.cli.core: profile 0.007 2 8
DEBUG: cli.azure.cli.core: privatedns 0.060 14 60
DEBUG: cli.azure.cli.core: redis 0.005 7 38
DEBUG: cli.azure.cli.core: relay 0.067 7 8
DEBUG: cli.azure.cli.core: rdbms 0.086 22 90
DEBUG: cli.azure.cli.core: role 0.004 17 62
DEBUG: cli.azure.cli.core: search 0.025 7 20
DEBUG: cli.azure.cli.core: security 0.020 47 98
DEBUG: cli.azure.cli.core: resource 0.077 52 234
DEBUG: cli.azure.cli.core: servicebus 0.026 14 17
DEBUG: cli.azure.cli.core: serviceconnector 0.029 20 331
DEBUG: cli.azure.cli.core: signalr 0.004 10 42
DEBUG: cli.azure.cli.core: servicefabric 0.039 27 80
DEBUG: cli.azure.cli.core: sql 0.025 57 222
DEBUG: cli.azure.cli.core: storage 0.061 61 278
DEBUG: cli.azure.cli.core: sqlvm 0.079 4 20
DEBUG: cli.azure.cli.core: util 0.003 3 7
DEBUG: cli.azure.cli.core: synapse 0.017 54 246
DEBUG: cli.azure.cli.core: vm 0.160 60 207
DEBUG: cli.azure.cli.core: monitor 0.816 17 63
DEBUG: cli.azure.cli.core: network 0.801 107 352
DEBUG: cli.azure.cli.core: Total (66) 1.542 1203 4705
DEBUG: cli.azure.cli.core: Loaded 1189 groups, 4705 commands.
DEBUG: cli.azure.cli.core: Updated command index in 0.003 seconds.
DEBUG: cli.azure.cli.core: Cached top-level help with 91 groups and 10 commands
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPreCommandTableTruncate [<function AzCliLogging.init_command_file_logging at 0x7bb09143b380>]
DEBUG: cli.azure.cli.core.azlogging: metadata file logging enabled - writing logs to '/home/frazar/.azure/commands/2026-03-05.17-15-42.extension_add.2673.log'.
INFO: az_command_data_logger: command args: extension add --name {} --debug
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPreArgumentLoad [<function register_global_subscription_argument.<locals>.add_subscription_parameter at 0x7bb091488e00>]
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPostArgumentLoad []
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPostCommandTableCreate [<function register_ids_argument.<locals>.add_ids_arguments at 0x7bb09148b100>, <function register_cache_arguments.<locals>.add_cache_arguments at 0x7bb09148b2e0>, <function register_upcoming_breaking_change_info.<locals>.update_breaking_change_info at 0x7bb09148b380>]
DEBUG: cli.knack.cli: Event: CommandInvoker.OnCommandTableLoaded []
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPreParseArgs [<function _documentdb_deprecate at 0x7bb089ef6b60>]
DEBUG: cli.knack.cli: Event: CommandInvoker.OnPostParseArgs [<function OutputProducer.handle_output_argument at 0x7bb092276700>, <function CLIQuery.handle_query_parameter at 0x7bb0922ac860>, <function register_ids_argument.<locals>.parse_ids_arguments at 0x7bb09148b1a0>]
DEBUG: urllib3.connectionpool: Starting new HTTPS connection (1): aka.ms:443
DEBUG: urllib3.connectionpool: https://aka.ms:443 "GET /azure-cli-extension-index-v1 HTTP/1.1" 301 0
DEBUG: urllib3.connectionpool: Starting new HTTPS connection (1): azcliextensionsync.blob.core.windows.net:443
DEBUG: urllib3.connectionpool: https://azcliextensionsync.blob.core.windows.net:443 "GET /index1/index.json HTTP/1.1" 200 4585303
INFO: cli.azure.cli.core.extension._resolve: No preview versions need to be tried.
DEBUG: cli.azure.cli.core.extension._resolve: Candidates ['azure_devops-0.12.0-py2.py3-none-any.whl', 'azure_devops-0.17.0-py2.py3-none-any.whl', 'azure_devops-0.21.0-py2.py3-none-any.whl', 'azure_devops-0.26.0-py2.py3-none-any.whl', 'azure_devops-1.0.0-py2.py3-none-any.whl', 'azure_devops-1.0.1-py2.py3-none-any.whl', 'azure_devops-1.0.2-py2.py3-none-any.whl']
DEBUG: cli.azure.cli.core.extension._resolve: Candidates ['azure_devops-0.12.0-py2.py3-none-any.whl', 'azure_devops-0.17.0-py2.py3-none-any.whl', 'azure_devops-0.21.0-py2.py3-none-any.whl', 'azure_devops-0.26.0-py2.py3-none-any.whl', 'azure_devops-1.0.0-py2.py3-none-any.whl', 'azure_devops-1.0.1-py2.py3-none-any.whl', 'azure_devops-1.0.2-py2.py3-none-any.whl']
DEBUG: cli.azure.cli.core.extension._resolve: Candidates ['azure_devops-0.12.0-py2.py3-none-any.whl', 'azure_devops-0.17.0-py2.py3-none-any.whl', 'azure_devops-0.21.0-py2.py3-none-any.whl', 'azure_devops-0.26.0-py2.py3-none-any.whl', 'azure_devops-1.0.0-py2.py3-none-any.whl', 'azure_devops-1.0.1-py2.py3-none-any.whl', 'azure_devops-1.0.2-py2.py3-none-any.whl']
DEBUG: cli.azure.cli.core.extension._resolve: Candidates ['azure_devops-0.12.0-py2.py3-none-any.whl', 'azure_devops-0.17.0-py2.py3-none-any.whl', 'azure_devops-0.21.0-py2.py3-none-any.whl', 'azure_devops-0.26.0-py2.py3-none-any.whl', 'azure_devops-1.0.0-py2.py3-none-any.whl', 'azure_devops-1.0.1-py2.py3-none-any.whl', 'azure_devops-1.0.2-py2.py3-none-any.whl']
DEBUG: cli.azure.cli.core.extension._resolve: Candidates ['azure_devops-0.12.0-py2.py3-none-any.whl', 'azure_devops-0.17.0-py2.py3-none-any.whl', 'azure_devops-0.21.0-py2.py3-none-any.whl', 'azure_devops-0.26.0-py2.py3-none-any.whl', 'azure_devops-1.0.0-py2.py3-none-any.whl', 'azure_devops-1.0.1-py2.py3-none-any.whl', 'azure_devops-1.0.2-py2.py3-none-any.whl']
DEBUG: cli.azure.cli.core.extension._resolve: Chosen {'downloadUrl': 'https://azcliprod.blob.core.windows.net/cli-extensions/azure_devops-1.0.2-py2.py3-none-any.whl', 'filename': 'azure_devops-1.0.2-py2.py3-none-any.whl', 'metadata': {'azext.minCliCoreVersion': '2.30.0', 'classifiers': ['Development Status :: 4 - Beta', 'Intended Audience :: Developers', 'Intended Audience :: System Administrators', 'Programming Language :: Python', 'Programming Language :: Python :: 3', 'Programming Language :: Python :: 3.4', 'Programming Language :: Python :: 3.5', 'Programming Language :: Python :: 3.6', 'License :: OSI Approved :: MIT License'], 'extensions': {'python.details': {'contacts': [{'email': 'VSTS_Social@microsoft.com', 'name': 'Microsoft', 'role': 'author'}], 'document_names': {'description': 'DESCRIPTION.rst'}, 'project_urls': {'Home': 'https://github.com/Microsoft/azure-devops-cli-extension'}}}, 'extras': [], 'generator': 'bdist_wheel (0.30.0)', 'license': 'MIT', 'metadata_version': '2.0', 'name': 'azure-devops', 'run_requires': [{'requires': ['distro (>=1.6.0)']}], 'summary': 'Tools for managing Azure DevOps.', 'version': '1.0.2'}, 'sha256Digest': 'e2b0de02a3a745128c3f6e8c2711b8bbdbc1ba8b3afd2408a1581f35b069ba59'}
DEBUG: cli.azure.cli.core.extension.operations: Extension source is url? True
DEBUG: cli.azure.cli.core.extension.operations: Downloading https://azcliprod.blob.core.windows.net/cli-extensions/azure_devops-1.0.2-py2.py3-none-any.whl to /tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl
DEBUG: urllib3.connectionpool: Starting new HTTPS connection (1): azcliprod.blob.core.windows.net:443
DEBUG: urllib3.connectionpool: https://azcliprod.blob.core.windows.net:443 "GET /cli-extensions/azure_devops-1.0.2-py2.py3-none-any.whl HTTP/1.1" 200 1198093
DEBUG: cli.azure.cli.core.extension.operations: Downloaded to /tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl
DEBUG: cli.azure.cli.core.extension.operations: Validating the extension /tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl
DEBUG: cli.azure.cli.core.extension.operations: Checksum of /tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl is OK
DEBUG: cli.azure.cli.core.extension.operations: Validation successful on /tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl
DEBUG: cli.azure.cli.core.extension.operations: Linux distro check: Reading from: /etc/apt/sources.list.d/azure-cli.list
DEBUG: cli.azure.cli.core.extension.operations: Linux distro check: An error occurred while checking linux distribution version source list consistency.
DEBUG: cli.azure.cli.core.extension.operations: [Errno 2] No such file or directory: '/etc/apt/sources.list.d/azure-cli.list'
DEBUG: cli.azure.cli.core.extension.operations: Executing pip with args: ['install', '--target', '/home/frazar/.azure/cliextensions/azure-devops', '/tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl']
DEBUG: cli.azure.cli.core.extension.operations: Running: ['/opt/az/bin/python3', '-m', 'pip', 'install', '--target', '/home/frazar/.azure/cliextensions/azure-devops', '/tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl', '--disable-pip-version-check', '--no-cache-dir']
DEBUG: cli.azure.cli.core.extension.operations: ERROR: Could not find an activated virtualenv (required).
DEBUG: cli.azure.cli.core.extension.operations: Command '['/opt/az/bin/python3', '-m', 'pip', 'install', '--target', '/home/frazar/.azure/cliextensions/azure-devops', '/tmp/tmpjdbyyspm/azure_devops-1.0.2-py2.py3-none-any.whl', '--disable-pip-version-check', '--no-cache-dir']' returned non-zero exit status 3.
DEBUG: cli.azure.cli.core.extension.operations: Pip failed so deleting anything we might have installed at /home/frazar/.azure/cliextensions/azure-devops
DEBUG: cli.azure.cli.core.azclierror: Traceback (most recent call last):
File "/opt/az/lib/python3.13/site-packages/knack/cli.py", line 233, in invoke
cmd_result = self.invocation.execute(args)
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 682, in execute
raise ex
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 812, in _run_jobs_serially
results.append(self._run_job(expanded_arg, cmd_copy))
~~~~~~~~~~~~~^^^^^^^^^^^^^^^^^^^^^^^^
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 781, in _run_job
result = cmd_copy(params)
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 336, in __call__
return self.handler(*args, **kwargs)
~~~~~~~~~~~~^^^^^^^^^^^^^^^^^
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/commands/command_operation.py", line 120, in handler
return op(**command_args)
File "/opt/az/lib/python3.13/site-packages/azure/cli/command_modules/extension/custom.py", line 16, in add_extension_cmd
return add_extension(cli_ctx=cmd.cli_ctx, source=source, extension_name=extension_name, index_url=index_url,
yes=yes, pip_extra_index_urls=pip_extra_index_urls, pip_proxy=pip_proxy, system=system,
version=version, upgrade=upgrade, allow_preview=allow_preview)
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/extension/operations.py", line 343, in add_extension
extension_name = _add_whl_ext(cli_ctx=cmd_cli_ctx, source=source, ext_sha256=ext_sha256,
pip_extra_index_urls=pip_extra_index_urls, pip_proxy=pip_proxy, system=system)
File "/opt/az/lib/python3.13/site-packages/azure/cli/core/extension/operations.py", line 172, in _add_whl_ext
raise CLIError('An error occurred. Pip failed with status code {}. '
'Use --debug for more information.'.format(pip_status_code))
knack.util.CLIError: An error occurred. Pip failed with status code 3. Use --debug for more information.
ERROR: cli.azure.cli.core.azclierror: An error occurred. Pip failed with status code 3. Use --debug for more information.
ERROR: az_command_data_logger: An error occurred. Pip failed with status code 3. Use --debug for more information.
DEBUG: cli.knack.cli: Event: Cli.PostExecute [<function AzCliLogging.deinit_cmd_metadata_logging at 0x7bb09143b600>]
INFO: az_command_data_logger: exit code: 1
INFO: cli.__main__: Command ran in 7.580 seconds (init: 0.094, invoke: 7.486)
INFO: telemetry.main: Begin splitting cli events and extra events, total events: 1
INFO: telemetry.client: Accumulated 0 events. Flush the clients.
INFO: telemetry.main: Finish splitting cli events and extra events, cli events: 1
INFO: telemetry.save: Save telemetry record of length 4157 in cache file under /home/frazar/.azure/telemetry/20260305171547744
INFO: telemetry.main: Begin creating telemetry upload process.
INFO: telemetry.process: Creating upload process: "/opt/az/bin/python3 /opt/az/lib/python3.13/site-packages/azure/cli/telemetry/__init__.py /home/frazar/.azure /home/frazar/.azure/telemetry/20260305171547744"
INFO: telemetry.process: Return from creating process 2697
INFO: telemetry.main: Finish creating telemetry upload process.
Expected behavior
The extension is installed correctly regardless of the value of PIP_REQUIRE_VIRTUALENV.
Environment Summary
azure-cli 2.84.0
core 2.84.0
telemetry 1.1.0
Dependencies:
msal 1.35.0b1
azure-mgmt-resource 24.0.0
Python location '/opt/az/bin/python3'
Config directory '/home/frazar/.azure'
Extensions directory '/home/frazar/.azure/cliextensions'
Python (Linux) 3.13.11 (main, Feb 25 2026, 02:29:34) [GCC 13.3.0]
Legal docs and information: aka.ms/AzureCliLegal
Your CLI is up-to-date.
Additional context
Here is a Dockerfile to reproduce the issue in a portable way:
FROM ubuntu:24.04
RUN apt-get update && apt-get install curl -y
RUN curl -sL https://aka.ms/InstallAzureCLIDeb | bash
ENV PIP_REQUIRE_VIRTUALENV=true
RUN az extension add --name azure-devops --debugStore the above in a file called Dockerfile then run docker build --progress=plain . in the same folder.