az extension add --name ssh - An error occurred. Pip failed with status code 2

[ryanberg026]

Describe the bug

hello,

I'm going crazy trying to get the ssh extension installed.

I've installed the most recent Azure cli 64 bit from Microsoft's website. I'm trying to utilize Azure arc for RDP to an arc enabled Windows system. I have installed the SSH server addin on the target host.

Below are the commands I'm running (i've left out the values). I'm asked to install the ssh extension, I choose Y. It ends in "An error occurred. Pip failed with status code 2"

az login
az ssh arc --resource-group --vm-name --local-user --rdp

The command requires the extension ssh. Do you want to install it now? The command will continue to run after the extension is installed. (Y/n):

An error occurred. Pip failed with status code 2

Related command

az login
az ssh arc --resource-group --vm-name --local-user --rdp

Errors

An error occurred. Pip failed with status code 2

Issue script & Debug output

cli.knack.cli: Command arguments: ['ssh', 'arc', '--resource-group', 'oec-east2-dev-it-internal-rg', '--vm-name', 'US702NTB0559', '--local-user', 'rb.jfk', '--rdp', '--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 [<function CLILogging.on_global_arguments at 0x00000202568C0900>, <function OutputProducer.on_global_arguments at 0x00000202571504A0>, <function CLIQuery.on_global_arguments at 0x000002025717D8A0>]
cli.knack.cli: Event: CommandInvoker.OnPreCommandTableCreate []
cli.azure.cli.core: No module found from index for '['ssh', 'arc', '--resource-group', 'oec-east2-dev-it-internal-rg', '--vm-name', 'US702NTB0559', '--local-user', 'rb.jfk', '--rdp', '--debug']'
cli.azure.cli.core: Loading all modules and extensions
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', 'privatedns', 'profile', 'rdbms', 'redis', 'relay', 'resource', 'role', 'search', 'security', 'servicebus', 'serviceconnector', 'servicefabric', 'signalr', 'sql', 'sqlvm', 'storage', 'synapse', 'util', 'vm']
cli.azure.cli.core: Loading command modules:
cli.azure.cli.core: Name Load Time Groups Commands
cli.azure.cli.core: acr 0.170 36 149
cli.azure.cli.core: acs 0.018 15 79
cli.azure.cli.core: advisor 0.002 3 6
cli.azure.cli.core: ams 0.004 22 100
cli.azure.cli.core: apim 0.006 14 69
cli.azure.cli.core: appconfig 0.002 9 47
cli.azure.cli.core: appservice 0.019 80 277
cli.azure.cli.core: aro 0.011 1 10
cli.azure.cli.core: backup 0.003 16 60
cli.azure.cli.core: batch 0.038 32 96
cli.azure.cli.core: batchai 0.003 10 30
cli.azure.cli.core: billing 0.012 19 53
cli.azure.cli.core: botservice 0.003 12 42
cli.azure.cli.core: cdn 0.122 8 50
cli.azure.cli.core: cloud 0.002 1 7
cli.azure.cli.core: cognitiveservices 0.002 10 33
cli.azure.cli.core: compute_recommender 0.003 1 1
cli.azure.cli.core: computefleet 0.007 1 1
cli.azure.cli.core: config 0.001 2 7
cli.azure.cli.core: configure 0.001 2 5
cli.azure.cli.core: consumption 0.017 8 9
cli.azure.cli.core: container 0.007 2 17
cli.azure.cli.core: containerapp 0.093 37 123
cli.azure.cli.core: cosmosdb 0.010 58 200
cli.azure.cli.core: databoxedge 0.007 5 28
cli.azure.cli.core: dls 0.002 6 36
cli.azure.cli.core: dms 0.002 3 22
cli.azure.cli.core: eventgrid 0.003 25 96
cli.azure.cli.core: eventhubs 0.010 14 21
cli.azure.cli.core: extension 0.001 1 7
cli.azure.cli.core: feedback 0.001 1 2
cli.azure.cli.core: find 0.001 1 1
cli.azure.cli.core: hdinsight 0.007 9 42
cli.azure.cli.core: identity 0.006 2 7
cli.azure.cli.core: interactive 0.000 1 1
cli.azure.cli.core: iot 0.221 19 82
cli.azure.cli.core: keyvault 0.007 20 114
cli.azure.cli.core: lab 0.050 9 30
cli.azure.cli.core: managedservices 0.009 3 8
cli.azure.cli.core: maps 0.002 5 13
cli.azure.cli.core: marketplaceordering 0.003 1 2
cli.azure.cli.core: monitor 0.202 18 64
cli.azure.cli.core: mysql 0.106 16 56
cli.azure.cli.core: netappfiles 0.050 8 15
cli.azure.cli.core: network 0.059 105 350
cli.azure.cli.core: policyinsights 0.015 9 17
cli.azure.cli.core: privatedns 0.018 14 60
cli.azure.cli.core: profile 0.002 2 8
cli.azure.cli.core: rdbms 0.060 52 217
cli.azure.cli.core: redis 0.002 7 38
cli.azure.cli.core: relay 0.021 7 8
cli.azure.cli.core: resource 0.011 52 232
cli.azure.cli.core: role 0.002 17 62
cli.azure.cli.core: search 0.006 7 19
cli.azure.cli.core: security 0.009 48 98
cli.azure.cli.core: servicebus 0.007 13 17
cli.azure.cli.core: serviceconnector 0.014 20 331
cli.azure.cli.core: servicefabric 0.012 27 80
cli.azure.cli.core: signalr 0.002 10 42
cli.azure.cli.core: sql 0.010 56 215
cli.azure.cli.core: sqlvm 0.016 4 20
cli.azure.cli.core: storage 0.073 60 275
cli.azure.cli.core: synapse 0.006 54 246
cli.azure.cli.core: util 0.001 3 7
cli.azure.cli.core: vm 0.048 59 262
cli.azure.cli.core: Total (65) 1.638 1192 4722
cli.azure.cli.core: Loaded 1178 groups, 4722 commands.
cli.azure.cli.core: Updated command index in 0.002 seconds.
cli.knack.cli: Event: CommandInvoker.OnPreCommandTableTruncate [<function AzCliLogging.init_command_file_logging at 0x000002025753B060>]
cli.azure.cli.core.azlogging: metadata file logging enabled - writing logs to 'C:\Users\rb.jfk.azure\commands\2025-06-13.16-36-07.ssh.17672.log'.
az_command_data_logger: command args: ssh {} --resource-group {} --vm-name {} --local-user {} --rdp --debug
cli.knack.cli: Event: CommandInvoker.OnPreArgumentLoad [<function register_global_subscription_argument..add_subscription_parameter at 0x0000020257587920>]
cli.knack.cli: Event: CommandInvoker.OnPostArgumentLoad []
cli.knack.cli: Event: CommandInvoker.OnPostCommandTableCreate [<function register_ids_argument..add_ids_arguments at 0x00000202575A5BC0>, <function register_cache_arguments..add_cache_arguments at 0x00000202575A5D00>, <function register_upcoming_breaking_change_info..update_breaking_change_info at 0x00000202575A5DA0>]
cli.knack.cli: Event: CommandInvoker.OnCommandTableLoaded []
cli.knack.cli: Event: CommandInvoker.OnPreParseArgs [<function _documentdb_deprecate at 0x0000020259C00B80>]
cli.azure.cli.core.extension.dynamic_install: Preview version of extension is disabled by default for extension installation, enabled for modules without stable versions.
cli.azure.cli.core.extension.dynamic_install: Please run 'az config set extension.dynamic_install_allow_preview=true or false' to config it specifically.
The command requires the extension ssh. Do you want to install it now? The command will continue to run after the extension is installed. (Y/n): Y
cli.azure.cli.core.extension.dynamic_install: Run 'az config set extension.use_dynamic_install=yes_without_prompt' to allow installing extensions without prompt.
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 5358001
cli.azure.cli.core.extension._resolve: Candidates ['ssh-0.1.0-py3-none-any.whl', 'ssh-0.1.4-py3-none-any.whl', 'ssh-0.1.5-py3-none-any.whl', 'ssh-0.1.6-py3-none-any.whl', 'ssh-0.1.7-py3-none-any.whl', 'ssh-0.1.8-py3-none-any.whl', 'ssh-1.0.0-py3-none-any.whl', 'ssh-1.0.1-py3-none-any.whl', 'ssh-1.1.0-py3-none-any.whl', 'ssh-1.1.1-py3-none-any.whl', 'ssh-1.1.2-py3-none-any.whl', 'ssh-1.1.3-py3-none-any.whl', 'ssh-1.1.4-py3-none-any.whl', 'ssh-1.1.5-py3-none-any.whl', 'ssh-1.1.6-py3-none-any.whl', 'ssh-2.0.0-py3-none-any.whl', 'ssh-2.0.1-py3-none-any.whl', 'ssh-2.0.2-py3-none-any.whl', 'ssh-2.0.3-py3-none-any.whl', 'ssh-2.0.4-py3-none-any.whl', 'ssh-2.0.5-py3-none-any.whl', 'ssh-2.0.6-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['ssh-0.1.0-py3-none-any.whl', 'ssh-0.1.4-py3-none-any.whl', 'ssh-0.1.5-py3-none-any.whl', 'ssh-0.1.6-py3-none-any.whl', 'ssh-0.1.7-py3-none-any.whl', 'ssh-0.1.8-py3-none-any.whl', 'ssh-1.0.0-py3-none-any.whl', 'ssh-1.0.1-py3-none-any.whl', 'ssh-1.1.0-py3-none-any.whl', 'ssh-1.1.1-py3-none-any.whl', 'ssh-1.1.2-py3-none-any.whl', 'ssh-1.1.3-py3-none-any.whl', 'ssh-1.1.4-py3-none-any.whl', 'ssh-1.1.5-py3-none-any.whl', 'ssh-1.1.6-py3-none-any.whl', 'ssh-2.0.0-py3-none-any.whl', 'ssh-2.0.1-py3-none-any.whl', 'ssh-2.0.2-py3-none-any.whl', 'ssh-2.0.3-py3-none-any.whl', 'ssh-2.0.4-py3-none-any.whl', 'ssh-2.0.5-py3-none-any.whl', 'ssh-2.0.6-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['ssh-1.0.1-py3-none-any.whl', 'ssh-1.1.0-py3-none-any.whl', 'ssh-1.1.1-py3-none-any.whl', 'ssh-1.1.2-py3-none-any.whl', 'ssh-1.1.3-py3-none-any.whl', 'ssh-1.1.4-py3-none-any.whl', 'ssh-1.1.5-py3-none-any.whl', 'ssh-1.1.6-py3-none-any.whl', 'ssh-2.0.0-py3-none-any.whl', 'ssh-2.0.1-py3-none-any.whl', 'ssh-2.0.2-py3-none-any.whl', 'ssh-2.0.3-py3-none-any.whl', 'ssh-2.0.4-py3-none-any.whl', 'ssh-2.0.5-py3-none-any.whl', 'ssh-2.0.6-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['ssh-1.0.1-py3-none-any.whl', 'ssh-1.1.0-py3-none-any.whl', 'ssh-1.1.1-py3-none-any.whl', 'ssh-1.1.2-py3-none-any.whl', 'ssh-1.1.3-py3-none-any.whl', 'ssh-1.1.4-py3-none-any.whl', 'ssh-1.1.5-py3-none-any.whl', 'ssh-1.1.6-py3-none-any.whl', 'ssh-2.0.0-py3-none-any.whl', 'ssh-2.0.1-py3-none-any.whl', 'ssh-2.0.2-py3-none-any.whl', 'ssh-2.0.3-py3-none-any.whl', 'ssh-2.0.4-py3-none-any.whl', 'ssh-2.0.5-py3-none-any.whl', 'ssh-2.0.6-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Candidates ['ssh-1.0.1-py3-none-any.whl', 'ssh-1.1.0-py3-none-any.whl', 'ssh-1.1.1-py3-none-any.whl', 'ssh-1.1.2-py3-none-any.whl', 'ssh-1.1.3-py3-none-any.whl', 'ssh-1.1.4-py3-none-any.whl', 'ssh-1.1.5-py3-none-any.whl', 'ssh-1.1.6-py3-none-any.whl', 'ssh-2.0.0-py3-none-any.whl', 'ssh-2.0.1-py3-none-any.whl', 'ssh-2.0.2-py3-none-any.whl', 'ssh-2.0.3-py3-none-any.whl', 'ssh-2.0.4-py3-none-any.whl', 'ssh-2.0.5-py3-none-any.whl', 'ssh-2.0.6-py3-none-any.whl']
cli.azure.cli.core.extension._resolve: Chosen {'downloadUrl': 'https://azcliprod.blob.core.windows.net/cli-extensions/ssh-2.0.6-py3-none-any.whl', 'filename': 'ssh-2.0.6-py3-none-any.whl', 'metadata': {'azext.isPreview': False, 'azext.minCliCoreVersion': '2.45.0', 'classifiers': ['Development Status :: 4 - Beta', 'Intended Audience :: Developers', 'Intended Audience :: System Administrators', 'Programming Language :: Python', 'Programming Language :: Python :: 3', 'Programming Language :: Python :: 3.6', 'Programming Language :: Python :: 3.7', 'Programming Language :: Python :: 3.8', 'License :: OSI Approved :: MIT License'], 'extensions': {'python.details': {'contacts': [{'email': 'azpycli@microsoft.com', 'name': 'Microsoft Corporation', 'role': 'author'}], 'document_names': {'description': 'DESCRIPTION.rst'}, 'project_urls': {'Home': 'https://github.com/Azure/azure-cli-extensions/tree/main/src/ssh'}}}, 'extras': [], 'generator': 'bdist_wheel (0.30.0)', 'license': 'MIT', 'metadata_version': '2.0', 'name': 'ssh', 'run_requires': [{'requires': ['oras (==0.1.30)', 'oras==0.1.30', 'oschmod (==0.3.12)', 'oschmod==0.3.12']}], 'summary': 'SSH into Azure VMs using RBAC and AAD OpenSSH Certificates', 'version': '2.0.6'}, 'sha256Digest': '3d2206b4e6bdd56c69cc509ab99e5de6dc7f66d091b0185b7a3b557d8dc182cb'}
cli.azure.cli.core.extension.operations: Extension source is url? True
cli.azure.cli.core.extension.operations: Downloading https://azcliprod.blob.core.windows.net/cli-extensions/ssh-2.0.6-py3-none-any.whl to C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl
urllib3.connectionpool: Starting new HTTPS connection (1): azcliprod.blob.core.windows.net:443
urllib3.connectionpool: https://azcliprod.blob.core.windows.net:443 "GET /cli-extensions/ssh-2.0.6-py3-none-any.whl HTTP/1.1" 200 93412
cli.azure.cli.core.extension.operations: Downloaded to C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl
cli.azure.cli.core.extension.operations: Validating the extension C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl
cli.azure.cli.core.extension.operations: Checksum of C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl is OK
cli.azure.cli.core.extension.operations: Validation successful on C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl
cli.azure.cli.core.extension.operations: Executing pip with args: ['install', '--target', 'C:\Users\rb.jfk\.azure\cliextensions\ssh', 'C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-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\rb.jfk\.azure\cliextensions\ssh', 'C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl', '--disable-pip-version-check', '--no-cache-dir']
cli.azure.cli.core.extension.operations: Processing c:\users\rb.jfk\appdata\local\temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl
ERROR: Exception:
Traceback (most recent call last):
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\base_command.py", line 105, in _run_wrapper
status = _inner_run()
^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\base_command.py", line 96, in _inner_run
return self.run(options, args)
^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\cli\req_command.py", line 68, in wrapper
return func(self, options, args)
^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\commands\install.py", line 387, in run
requirement_set = resolver.resolve(
^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\resolution\resolvelib\resolver.py", line 96, in resolve
result = self._result = resolver.resolve(
^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\resolvelib\resolvers\resolution.py", line 515, in resolve
state = resolution.resolve(requirements, max_rounds=max_rounds)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\resolvelib\resolvers\resolution.py", line 444, in resolve
failure_criterion = self._attempt_to_pin_criterion(name)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\resolvelib\resolvers\resolution.py", line 211, in _attempt_to_pin_criterion
criteria = self._get_updated_criteria(candidate)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\resolvelib\resolvers\resolution.py", line 202, in _get_updated_criteria
self._add_to_criteria(criteria, requirement, parent=candidate)
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\resolvelib\resolvers\resolution.py", line 141, in _add_to_criteria
if not criterion.candidates:
^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\resolvelib\structs.py", line 194, in bool
return bool(self._sequence)
^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\resolution\resolvelib\found_candidates.py", line 163, in bool
self._bool = any(self)
^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\resolution\resolvelib\found_candidates.py", line 147, in
return (c for c in iterator if id(c) not in self._incompatible_ids)
^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\resolution\resolvelib\found_candidates.py", line 33, in _iter_built
for version, func in infos:
^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\resolution\resolvelib\factory.py", line 307, in iter_index_candidate_infos
result = self._finder.find_best_candidate(
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\package_finder.py", line 906, in find_best_candidate
candidates = self.find_all_candidates(project_name)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\package_finder.py", line 843, in find_all_candidates
page_candidates = list(page_candidates_it)
^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\sources.py", line 193, in page_candidates
yield from self._candidates_from_page(self._link)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\package_finder.py", line 801, in process_project_url
index_response = self._link_collector.fetch_response(project_url)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\collector.py", line 448, in fetch_response
return _get_index_content(location, session=self.session)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\collector.py", line 352, in _get_index_content
resp = _get_simple_response(url, session=session)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\index\collector.py", line 131, in _get_simple_response
resp = session.get(
^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\requests\sessions.py", line 602, in get
return self.request("GET", url, **kwargs)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_internal\network\session.py", line 523, in request
return super().request(method, url, *args, **kwargs)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\requests\sessions.py", line 589, in request
resp = self.send(prep, **send_kwargs)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\requests\sessions.py", line 703, in send
r = adapter.send(request, **kwargs)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\requests\adapters.py", line 667, in send
resp = conn.urlopen(
^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\urllib3\connectionpool.py", line 716, in urlopen
httplib_response = self._make_request(
^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\urllib3\connectionpool.py", line 404, in _make_request
self._validate_conn(conn)
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\urllib3\connectionpool.py", line 1061, in _validate_conn
conn.connect()
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\urllib3\connection.py", line 406, in connect
context.verify_mode = resolve_cert_reqs(self.cert_reqs)
^^^^^^^^^^^^^^^^^^^
File "C:\Program Files\Microsoft SDKs\Azure\CLI2\Lib\site-packages\pip_vendor\truststore_api.py", line 292, in verify_mode
_original_super_SSLContext.verify_mode.set( # type: ignore[attr-defined]
File "ssl.py", line 679, in verify_mode
File "ssl.py", line 679, in verify_mode
File "ssl.py", line 679, in verify_mode
[Previous line repeated 959 more times]
RecursionError: maximum recursion depth exceeded

cli.azure.cli.core.extension.operations: Command '['C:\Program Files\Microsoft SDKs\Azure\CLI2\python.exe', '-m', 'pip', 'install', '--target', 'C:\Users\rb.jfk\.azure\cliextensions\ssh', 'C:\Users\rb.jfk\AppData\Local\Temp\tmpig9tq0z1\ssh-2.0.6-py3-none-any.whl', '--disable-pip-version-check', '--no-cache-dir']' returned non-zero exit status 2.
cli.azure.cli.core.extension.operations: Pip failed so deleting anything we might have installed at C:\Users\rb.jfk.azure\cliextensions\ssh
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 591, in execute
File "D:\a_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\knack/parser.py", line 261, in parse_args
File "argparse.py", line 1904, in parse_args
File "D:\a_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/parser.py", line 281, in parse_known_args
File "argparse.py", line 1914, in parse_known_args
File "argparse.py", line 1943, in _parse_known_args2
File "argparse.py", line 2165, in _parse_known_args
File "argparse.py", line 2141, in consume_positionals
File "argparse.py", line 2003, in take_action
File "D:\a_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/parser.py", line 272, in _get_values
File "argparse.py", line 2523, in _get_values
File "D:\a_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/parser.py", line 300, in _check_value
File "D:\a_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/extension/dynamic_install.py", line 132, in try_install_extension
File "D:\a_work\1\s\build_scripts\windows\artifacts\cli\Lib\site-packages\azure/cli/core/extension/dynamic_install.py", line 242, in _check_value_in_extensions
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 2. Use --debug for more information.

cli.azure.cli.core.azclierror: An error occurred. Pip failed with status code 2. Use --debug for more information.
az_command_data_logger: An error occurred. Pip failed with status code 2. Use --debug for more information.
cli.knack.cli: Event: Cli.PostExecute [<function AzCliLogging.deinit_cmd_metadata_logging at 0x000002025753B2E0>]
az_command_data_logger: exit code: 1
cli.main: Command ran in 16.706 seconds (init: 0.358, invoke: 16.348)
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 4020 in cache file under C:\Users\rb.jfk.azure\telemetry\20250613163622593
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\rb.jfk.azure C:\Users\rb.jfk.azure\telemetry\20250613163622593"
telemetry.process: Return from creating process 12304
telemetry.main: Finish creating telemetry upload process.

Expected behavior

I should be able to install the extension as a dependency & then complete running the command to RDP to the target system.

Environment Summary

azure-cli 2.74.0

core 2.74.0
telemetry 1.1.0

Dependencies:
msal 1.32.3
azure-mgmt-resource 23.3.0

Python location 'C:\Program Files\Microsoft SDKs\Azure\CLI2\python.exe'
Config directory 'C:\Users\rb.jfk.azure'
Extensions directory 'C:\Users\rb.jfk.azure\cliextensions'

Python (Windows) 3.12.10 (tags/v3.12.10:0cc8128, Apr 8 2025, 12:21:36) [MSC v.1943 64 bit (AMD64)]

Legal docs and information: aka.ms/AzureCliLegal

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.

• bastion extension not installing on copilot pc #30684
• Unable to install extension using azure-cli 2.0.55. #8315
• az failed to install ml #29892

---

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

Solution 1:

Try this command python -m pip install --upgrade pip. This will upgrade pip and you should be unblocked post that.

Reference:

• Unable to install extension using azure-cli 2.0.55. #8315 (comment)

Solution 2:

Confirmed that the Workaround solved the issue. I have conda installed on my machine, which was interfering with the install.

Reference:

• bastion extension not installing on copilot pc #30684 (comment)

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