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brew update/brew upgrade failing with Error: Not a directory @ dir_s_rmdir error strikes back #2248

@traversaro

Description

@traversaro

Description
On some scheduled jobs on macOS, since a few hours the brew update and brew upgrade commands are failing.

Area for Triage:

Question, Bug, or Feature?:
Bug

Virtual environments affected

  • Ubuntu 16.04
  • Ubuntu 18.04
  • Ubuntu 20.04
  • macOS 10.15
  • macOS 11.0
  • Windows Server 2016 R2
  • Windows Server 2019

Expected behavior
The commands:

  • brew update
  • brew upgrade

Should work fine.

Actual behavior

  • brew update
  • brew upgrade
    commands fail with error:
2020-12-11T14:20:31.2785670Z �[34m==>�[0m �[1mPouring openssl@1.1-1.1.1i.catalina.bottle.tar.gz�[0m
2020-12-11T14:21:54.9827160Z �[31mError:�[0m Not a directory @ dir_s_rmdir - /usr/local/Cellar/openssl
2020-12-11T14:21:54.9844860Z �[34m==>�[0m �[1mCaveats�[0m

See for example https://github.com/robotology/robotology-superbuild/runs/1534684566?check_suite_focus=true .

Repro steps
A description with steps to reproduce the issue. If your have a public example or repo to share,
please provide the link.

  1. Run brew update
  2. Run brew upgrade

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