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

Area for Triage:

Question, Bug, or Feature?:

Bug

Virtual environments affected

• macOS 10.15
• Ubuntu 16.04 LTS
• Ubuntu 18.04 LTS
• Ubuntu 20.04 LTS
• 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:

==> Summary
🍺  /usr/local/Cellar/node@12/12.19.0_1: 4,304 files, 59.5MB
Removing: /usr/local/Cellar/node@12/12.18.4... (4,296 files, 58.9MB)
Removing: /Users/runner/Library/Caches/Homebrew/node@12--12.18.4.catalina.bottle.tar.gz... (15.8MB)
Error: Not a directory @ dir_s_rmdir - /usr/local/Cellar/openssl
==> Upgrading openssl@1.1 1.1.1h -> 1.1.1h 
Removing: /usr/local/Cellar/openssl/1.0.2t... (1,787 files, 12.4MB)
Error: Process completed with exit code 1.

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