Cask not updating if older version exists in /usr/local/Caskroom

[Fafifoerniek]

Output of brew config

$ brew config
HOMEBREW_VERSION: 4.6.16-24-gafdef01
ORIGIN: https://github.com/Homebrew/brew
HEAD: afdef012e71c81c8e80956a2f5bfb6bbc95cea6a
Last commit: 50 minutes ago
Branch: main
Core tap JSON: 06 Oct 14:40 UTC
Core cask tap JSON: 06 Oct 14:40 UTC
HOMEBREW_PREFIX: /usr/local
HOMEBREW_CASK_OPTS: []
HOMEBREW_FORBID_PACKAGES_FROM_PATHS: set
HOMEBREW_MAKE_JOBS: 4
HOMEBREW_SORBET_RUNTIME: set
Homebrew Ruby: 3.4.5 => /usr/local/Homebrew/Library/Homebrew/vendor/portable-ruby/3.4.5/bin/ruby
CPU: quad-core 64-bit kabylake
Clang: 14.0.3 build 1403
Git: 2.39.2 => /Library/Developer/CommandLineTools/usr/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 13.7.8-x86_64
CLT: 14.3.1.0.1.1683849156
Xcode: N/A

Output of brew doctor

Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: A newer Command Line Tools release is available.
Update them from Software Update in System Settings.

If that doesn't show you any updates, run:
  sudo rm -rf /Library/Developer/CommandLineTools
  sudo xcode-select --install
Alternatively, manually download them from:
  https://developer.apple.com/download/all/.
You should download the Command Line Tools for Xcode 15.2.
This is a Tier 2 configuration:
  https://docs.brew.sh/Support-Tiers#tier-2
You can report Tier 2 unrelated issues to Homebrew/* repositories!
Read the above document instead before opening any issues or PRs.
Warning: You are using macOS 13.
We (and Apple) do not provide support for this old version.
This is a Tier 3 configuration:
  https://docs.brew.sh/Support-Tiers#tier-3
You can report Tier 3 unrelated issues to Homebrew/* repositories!
Read the above document instead before opening any issues or PRs.

Description of issue

I have a couple of casks installed with Homebrew for "ease of use" regarding upgrading all the casks in one go.
I have the following script running in macOS Ventura 13.7.8:

#!/bin/zsh
/usr/local/bin/brew update -v
/usr/local/bin/brew upgrade
/usr/local/bin/brew upgrade --greedy
/usr/local/bin/brew cleanup -s
rm -rf "$(brew --cache)"
/usr/local/bin/brew missing
/usr/local/bin/brew autoremove
/usr/local/bin/brew doctor
/usr/local/bin/brew bundle install --file "/Lokaal/Linux/brewfile.txt"
/usr/local/bin/brew bundle check --file "/Lokaal/Linux/brewfile.txt"
/usr/local/bin/brew bundle cleanup --file "~/Lokaal/Linux/brewfile.txt"
/usr/local/bin/brew bundle dump --file ~/Lokaal/Linux/brewfile.txt --describe --force
Lately I get error messages regarding some casks:

I got these messages with: leader-key, nordvpn, stats, tuta-mail, raycast, session, ... and the error message states that there is already an application "X" in "/usr/local/Caskroom". Once I delete the folder of the old version of the application X and re-run the script, everything goes smoothly and the new casks are installed.

Is this something I can arange myself in changing my script or is there something wrong in the Homebrew process of upgrading outdated casks?

Many thanks for advice.

Relevant casks

leader-key, nordvpn, stats, tuta-mail, raycast, session, …

[gromgit]

HOMEBREW_VERSION: 4.6.13-4-g4747ead
ORIGIN: https://github.com/Homebrew/brew
HEAD: 4747ead1c21073b1730213b94b889d368bb99334
Last commit: 19 hours ago
Branch: main
Core tap JSON: 25 Sep 06:18 UTC
Core cask tap JSON: 25 Sep 06:18 UTC

Your brew config output is almost two weeks old. Please post your current brew config output.

[Fafifoerniek]

Updated with the config of today, 14:40 UTC