Upgrade issue - 2.85 -> 2.87

[e-tobar]

This is autogenerated. Please review and update as needed.

Describe the bug

After az upgrade process I receive a erro message
Command Name
az upgrade

Errors:

Upgrade finished.
Traceback (most recent call last):
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/knack/cli.py", line 233, in invoke
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 677, in execute
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 820, in _run_jobs_serially
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/core/commands/__init__.py", line 805, in _run_job
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/core/util.py", line 682, in todict
ModuleNotFoundError: No module named 'azure.core'

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<frozen runpy>", line 198, in _run_module_as_main
  File "<frozen runpy>", line 88, in _run_code
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/__main__.py", line 41, in <module>
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/__main__.py", line 27, in cli_main
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/knack/cli.py", line 245, in invoke
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/core/__init__.py", line 157, in exception_handler
  File "/opt/homebrew/Cellar/azure-cli/2.85.0/libexec/lib/python3.13/site-packages/azure/cli/core/util.py", line 58, in handle_exception
ModuleNotFoundError: No module named 'jmespath'```

## To Reproduce:
Steps to reproduce the behavior. Note that argument values have been redacted, as they may contain sensitive information.

- _Put any pre-requisite steps here..._
- `az upgrade`

## Expected Behavior

## Environment Summary

macOS-26.5.1-arm64-arm-64bit-Mach-O, Darwin 25.5.0
Python 3.13.13
Installer: HOMEBREW

azure-cli 2.87.0

## Additional Context
==> Updating Homebrew...
Updated 1 tap (hashicorp/tap).
==> Outdated Formulae
azure-cli        ca-certificates  gitleaks         libsodium        openssl@3        python@3.13      sqlite           terraform        trivy

You have 9 outdated formulae installed.
You can upgrade them with brew upgrade
or list them with brew outdated.
==> Upgrading 1 outdated package:
azure-cli 2.85.0 -> 2.87.0
Warning: The following taps are not trusted:
  hashicorp/tap

Homebrew will ignore formulae, casks and commands from these taps when `HOMEBREW_REQUIRE_TAP_TRUST` is set.
This will become the default in Homebrew 6.0.0 or 5.2.0, whichever comes first.
Enable trust checks now with:
  export HOMEBREW_REQUIRE_TAP_TRUST=1
Trust specific formulae, casks or commands with:
  brew trust --formula <user>/<tap>/<formula>
  brew trust --cask <user>/<tap>/<cask>
  brew trust --command <user>/<tap>/<command>
or trust installed formulae from these taps with:
  brew trust --formula hashicorp/tap/terraform
You can trust all formulae, casks and commands from these taps with:
  brew trust hashicorp/tap
Prefer trusting only the specific formulae, casks or commands you need.
Untap them with:
  brew untap hashicorp/tap
To keep allowing them by default during the transition:
  export HOMEBREW_NO_REQUIRE_TAP_TRUST=1
This is not recommended and will be removed in a later release.
==> Downloading bottle manifests
✔︎ Bottle Manifest azure-cli (2.87.0)                                                                                                Downloaded   23.6KB/ 23.6KB
==> Fetching downloads for: azure-cli
✔︎ Bottle Manifest libsodium (1.0.22)                                                                                                Downloaded    7.3KB/  7.3KB
✔︎ Bottle Manifest ca-certificates (2026-05-14)                                                                                      Downloaded    1.7KB/  1.7KB
✔︎ Bottle Manifest openssl@3 (3.6.2)                                                                                                 Downloaded   12.0KB/ 12.0KB
✔︎ Bottle ca-certificates (2026-05-14)                                                                                               Downloaded  112.1KB/112.1KB
✔︎ Bottle Manifest sqlite (3.53.2)                                                                                                   Downloaded   11.8KB/ 11.8KB
✔︎ Bottle Manifest python@3.13 (3.13.13_1)                                                                                           Downloaded   28.0KB/ 28.0KB
✔︎ Bottle libsodium (1.0.22)                                                                                                         Downloaded  408.8KB/408.8KB
✔︎ Bottle sqlite (3.53.2)                                                                                                            Downloaded    2.4MB/  2.4MB
✔︎ Bottle openssl@3 (3.6.2)                                                                                                          Downloaded   10.9MB/ 10.9MB
✔︎ Bottle python@3.13 (3.13.13_1)                                                                                                    Downloaded   18.4MB/ 18.4MB
✔︎ Bottle azure-cli (2.87.0)                                                                                                         Downloaded   35.5MB/ 35.5MB
==> Upgrading azure-cli
  2.85.0 -> 2.87.0 
==> Installing dependencies for azure-cli: libsodium, ca-certificates, openssl@3, sqlite and python@3.13
==> Installing azure-cli dependency: libsodium
==> Pouring libsodium--1.0.22.arm64_tahoe.bottle.tar.gz
🍺  /opt/homebrew/Cellar/libsodium/1.0.22: 88 files, 1.1MB
==> Installing azure-cli dependency: ca-certificates
==> Pouring ca-certificates--2026-05-14.all.bottle.tar.gz
==> Regenerating CA certificate bundle from keychain, this may take a while...
🍺  /opt/homebrew/Cellar/ca-certificates/2026-05-14: 4 files, 200.9KB
==> Installing azure-cli dependency: openssl@3
==> Pouring openssl@3--3.6.2.arm64_tahoe.bottle.tar.gz
🍺  /opt/homebrew/Cellar/openssl@3/3.6.2: 7,627 files, 37.6MB
==> Installing azure-cli dependency: sqlite
==> Pouring sqlite--3.53.2.arm64_tahoe.bottle.tar.gz
🍺  /opt/homebrew/Cellar/sqlite/3.53.2: 13 files, 5.3MB
==> Installing azure-cli dependency: python@3.13
==> Pouring python@3.13--3.13.13_1.arm64_tahoe.bottle.1.tar.gz
🍺  /opt/homebrew/Cellar/python@3.13/3.13.13_1: 3,620 files, 72.3MB
==> Installing azure-cli
==> Pouring azure-cli--2.87.0.arm64_tahoe.bottle.tar.gz
🍺  /opt/homebrew/Cellar/azure-cli/2.87.0: 15,337 files, 320.3MB
==> Running `brew cleanup azure-cli`...
Disable this behaviour by setting `HOMEBREW_NO_INSTALL_CLEANUP=1`.
Hide these hints with `HOMEBREW_NO_ENV_HINTS=1` (see `man brew`).
Removing: /opt/homebrew/Cellar/azure-cli/2.85.0... (20,393 files, 468.8MB)
==> Caveats
zsh completions have been installed to:
  /opt/homebrew/share/zsh/site-functions
==> Upgraded 1 outdated package
azure-cli 2.85.0 -> 2.87.0


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[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.

• Error upgrading azure cli using Homebrew #23716

---

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

I ran into the same problem today and was able to get around it by re-installing it via homebrew:

brew uninstall azure-cli
brew cleanup
brew install azure-cli

Reference:

• Error upgrading azure cli using Homebrew #23716 (comment)

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