Permission errors when trying to install "Parallels Desktop for Mac"

[fabianschulz]

Output of brew config

HOMEBREW_VERSION: 4.4.24
ORIGIN: https://github.com/Homebrew/brew
HEAD: 2f6db3757e6c8533750264c0d397c3671665e2f4
Last commit: 2 days ago
Branch: stable
Core tap JSON: 11 Mar 21:29 UTC
Core cask tap JSON: 11 Mar 21:29 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: []
HOMEBREW_MAKE_JOBS: 14
Homebrew Ruby: 3.3.7 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.3.7/bin/ruby
CPU: 14-core 64-bit arm_brava
Clang: 16.0.0 build 1600
Git: 2.39.5 => /Library/Developer/CommandLineTools/usr/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 15.3.1-arm64
CLT: 16.2.0.0.1.1733547573
Xcode: N/A
Rosetta 2: false

Output of brew doctor

Your system is ready to brew.

Description of issue

Hi all,

on a brand new MacBook I tried to install cask "Parallels", but got tons of permission errors even after I entered my Admin password. Before trying anything which may mess up my Homebrew installation, I thought of maybe asking if it's clear why these errors were thrown.

I am not sure how to proceed - would anybody been able to give me advice how to fix my Parallels installation?

Here is the output:

fabian@MacBook ~ % brew install --cask parallels
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-cask/31656d137743c13779676eb5bf8d87904140268b/Casks/p/parallels.rb

100.0%

==> Downloading https://download.parallels.com/desktop/v20/20.2.2-55879/ParallelsDesktop-20.2.2-55879.dmg

100.0%

==> Installing Cask parallels
==> Moving App 'Parallels Desktop.app' to '/Applications/Parallels Desktop.app'
Password:
Mar 11 18:39:19 pdfm-bootstrap[14268] : inittool[14259]: Current umask: 0022
Mar 11 18:39:19 pdfm-bootstrap[14279] : inittool[14259]: '/Applications/Parallels Desktop.app/Contents/MacOS/Parallels Service' - incorrect permissions (0755)
Mar 11 18:39:19 pdfm-bootstrap[14280] : inittool[14259]: Last bundle location file was not found
Mar 11 18:39:19 pdfm-bootstrap[14281] : inittool[14259]: Bundle '/Applications/Parallels Desktop.app' (20.2.2-55879) is not initialized: let's cook it
Mar 11 18:39:19 pdfm-bootstrap[14282] : inittool[14259]: Set bundle owners to 'root:wheel'
chown: /Applications/Parallels Desktop.app/Contents/_CodeSignature/CodeResources: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/_CodeSignature: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prl_client_app: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prl_update_helper: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prlexec: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prl_disk_tool: Operation not permitted
...
chown: /Applications/Parallels Desktop.app/Contents/ ... hundreds of more chown errors in that directory
...
Mar 11 18:39:19 pdfm-bootstrap[14284] : inittool[14259]: Failed to set bundle owners
Mar 11 18:39:19 pdfm-bootstrap[14285] : inittool[14259]: Preinitialization failed
==> Backing App 'Parallels Desktop.app' up to '/opt/homebrew/Caskroom/parallels/20.2.2-55879/Parallels Desktop.app'
==> Removing App '/Applications/Parallels Desktop.app'
==> Purging files for version 20.2.2-55879 of Cask parallels
Error: Failure while executing; /usr/bin/sudo -E -- /Applications/Parallels\ Desktop.app/Contents/MacOS/inittool init exited with 1. Here's the output:
Mar 11 18:39:19 pdfm-bootstrap[14268] : inittool[14259]: Current umask: 0022
Mar 11 18:39:19 pdfm-bootstrap[14279] : inittool[14259]: '/Applications/Parallels Desktop.app/Contents/MacOS/Parallels Service' - incorrect permissions (0755)
Mar 11 18:39:19 pdfm-bootstrap[14280] : inittool[14259]: Last bundle location file was not found
Mar 11 18:39:19 pdfm-bootstrap[14281] : inittool[14259]: Bundle '/Applications/Parallels Desktop.app' (20.2.2-55879) is not initialized: let's cook it
Mar 11 18:39:19 pdfm-bootstrap[14282] : inittool[14259]: Set bundle owners to 'root:wheel'
chown: /Applications/Parallels Desktop.app/Contents/_CodeSignature/CodeResources: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/_CodeSignature: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prl_client_app: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prl_update_helper: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prlexec: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/prl_disk_tool: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/parallels_wrapper: Operation not permitted
chown: /Applications/Parallels Desktop.app/Contents/MacOS/Parallels Service: Operation not permitted
...
chown: /Applications/Parallels Desktop.app/Contents/ ... hundreds of more chown errors in that directory
...
Mar 11 18:39:19 pdfm-bootstrap[14284] : inittool[14259]: Failed to set bundle owners
Mar 11 18:39:19 pdfm-bootstrap[14285] : inittool[14259]: Preinitialization failed

Relevant casks

parallels

[fabianschulz]

Did some more research and will answer myself after finding: https://github.com/orgs/Homebrew/discussions/4159 (Terminal did not have full disk access, which I now have granted on my new Mac and did not know that this was required for this cask).

Quick question @SMillerDev (you had answered this in the other thread): is it OK to just run brew install --cask parallels again or do I manually need to uninstall the parallels cask before trying again with the proper disk permissions for Terminal?

[gromgit]

brew reinstall --cask parallels should do it.

[fabianschulz]

Thank you @gromgit , that did it. Appreciate your help!