Dock Command does not install correctly, causing the dock commands to skip

[gregorskii]

I am finding that installing the fork of the brew package does not work on my machine as it seems to require the sudo password to link correctly. I have to remote desktop into the node uninstall the dockutil command and reinstall it with interactivity, when I do tha it prompts for my password and installs correctly.

Any ideas? Anyone experiencing this?

[supercoffee]

I also have the same issue. It seems that the install step when run by ansible downloads dockutil to /opt/homebrew/Caskroom but does not symlink it. Possibly the interactive password step is breaking something. Everything works as expected if I uninstall and reinstall dockutil from the machine's local terminal.

[supercoffee]

@gregorskii I think I've figured it out.

When installing homebrew casks via the homebrew role, the sudo password is specified as an ansible variable.

- name: Install configured cask applications.
      homebrew_cask:
        name: "{{ item.name | default(item) }}"
        state: present
        install_options: "{{ item.install_options | default('appdir=' + homebrew_cask_appdir) }}"
        accept_external_apps: "{{ homebrew_cask_accept_external_apps }}"
        sudo_password: "{{ ansible_become_password | default(omit) }}"
      loop: "{{ homebrew_cask_apps }}"
      notify:
        - Clear homebrew cache

However, when using the dock role to install dockutil, no sudo password is specified.

- name: Install dockutil.
  community.general.homebrew_cask:
    name: "{{ dockutil_homebrew_cask }}"
    state: present
  notify:
    - Clear homebrew cache
  when: dockutil_install
  tags: ['dock']

When I first attempt to run the playbook with dockutil tasks on a remote machine, it hangs on the install step (presumably waiting for a sudo password that never gets inputted.
The second time I run the playbook, it skips over a bunch of items then fails with a cryptic permission error.

TASK [geerlingguy.mac.dock : See if TV is in the Dock.] *****************************************************************************************************************************************************************************
ok: [remote-mac.lan.example.com]

TASK [geerlingguy.mac.dock : Ensure Dock item TV is removed.] ***********************************************************************************************************************************************************************
skipping: [remote-mac.lan.example.com]

TASK [geerlingguy.mac.dock : Pause for 7 seconds between dock changes.] *************************************************************************************************************************************************************
skipping: [remote-mac.lan.example.com]

TASK [geerlingguy.mac.dock : Ensure required dock items exist.] *********************************************************************************************************************************************************************
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'Settings', 'path': '/Applications/System Settings.app/', 'pos': 2})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'Firefox', 'path': '/Applications/Firefox.app/', 'pos': 3})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'Firefox Developer Edition', 'path': '/Applications/Firefox Developer Edition.app/', 'pos': 4})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'WebStorm', 'path': '/Applications/WebStorm.app/', 'pos': 5})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'Datagrip', 'path': '/Applications/DataGrip.app/', 'pos': 7})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'Iterm', 'path': '/Applications/Iterm.app/', 'pos': 8})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'screenshots', 'path': '~/Pictures/screenshots/'})
included: /Users/myuser/.ansible/collections/ansible_collections/geerlingguy/mac/roles/dock/tasks/dock-add.yml for remote-mac.lan.example.com => (item={'name': 'Downloads', 'path': '~/Downloads/'})

TASK [geerlingguy.mac.dock : See if Dock item Settings exists.] *********************************************************************************************************************************************************************
ok: [remote-mac.lan.example.com]

TASK [geerlingguy.mac.dock : Get current dock section from output.] *****************************************************************************************************************************************************************
skipping: [remote-mac.lan.example.com]

TASK [geerlingguy.mac.dock : Ensure Dock item Settings exists.] *********************************************************************************************************************************************************************
fatal: [remote-mac.lan.example.com]: FAILED! => changed=false 
  cmd: dockutil --add '/Applications/System Settings.app/' --label Settings
  msg: '[Errno 13] Permission denied: b''dockutil'''
  rc: 13
  stderr: ''
  stderr_lines: <omitted>
  stdout: ''
  stdout_lines: <omitted>

When I log into the remote machine locally, I see that homebrew shows dockutil as installed, but running dockutil results in "command not found" indicating that homebrew didn't finish installing it. (Presumably because the first run hung up on the sudo password step.)

If I uninstall and reinstall dockutil on the machine locally and input the sudo password, then the dock role runs correctly.

So, I think the workaround here is to install dockutil by adding it to homebrew_cask_apps installed by the homebrew role since that role correctly installs casks that require sudo. Also make sure to define ansible_become_password in your inventory (see related issue)

[glennbrown]

Wanted to provide an update, I forked the repo and tried to add the sudo_password option and for the life of me I cannot get it to work. It either still prompts for the password even when specifying --ask-become-pass, if I add ansible_become_password via a lookup it will install but it won't actually create the /usr/local/bin/dockutil entry.

However putting in the homebrew_cask_apps variable and running the homebrew role like @supercoffee said it works just fine.

[glennbrown]

Took a break and I came back and compared the homebrew code again and noticed there was a become option in the block that was being executed. I have submitted PR #84 to fix it as long with a sleep for dock position settings.

Original Code:

- name: Install dockutil.
  community.general.homebrew_cask:
    name: "{{ dockutil_homebrew_cask }}"
    state: present
  notify:
    - Clear homebrew cache
  when: dockutil_install
  tags: ['dock']

Updated code

- name: Install dockutil
  become: "{{ (homebrew_user != ansible_user_id) | bool }}"
  become_user: "{{ homebrew_user }}"
  community.general.homebrew_cask:
    name: "{{ dockutil_homebrew_cask }}"
    state: present
  notify:
    - Clear homebrew cache
  when: dockutil_install
  tags: ['dock']

I still don't fully understand why this works fine but it does.

[Kylmakalle]

It looks like pathfinding is a little different for Casks and normal brew utils.
For remote systems, there's a common flaw with the way macOS handles paths. In short, ansible uses /bin/sh and macOS does not read any startup files when accessed via ssh. It will not read any files even with /bin/bash/
Back in 2021 I've encountered the same issue with remote macs and the easiest solution was hardcoding the PATH.

Today, I'm interested in local setup and I don't follow geerlingguy/mac-dev-playbook where Jeff installs dotfiles with PATH first and then runs dock setup.

I've ended up with:

1. Installing homebrew manually.
   Pre-installing homebrew also eliminates the Homebrew version check issue

   • homebrew_cask: unhelpful error when become_user set wrong ansible-collections/community.general#4708
   • related to TypeError during Homebrew Cask Installation of android-platform-tools on MacOS #92

2. Setting brew path before running dock role. For Apple Silicon it will be eval "$(/opt/homebrew/bin/brew shellenv)"

3. appending ~/.zprofile for future use of brew and utils installed via brew.

- name: Ensure .zprofile exists
  copy:
    content: ""
    dest: "/Users/{{ lookup('env', 'USER') }}/.zprofile"
    force: no

- name: Ensure brew path in ~/.zprofile
  lineinfile:
    state: present
    path: "/Users/{{ lookup('env', 'USER') }}/.zprofile"
    line: eval "$({{ (ansible_machine == 'arm64') | ternary('/opt/homebrew', '/usr/local') }}/bin/brew shellenv)"
  tags: ['homebrew']

or a shell script

echo "Installing brew..."
/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

echo "Updating ~/.zprofile ..."
if [[ "$(uname -m)" == "arm64" ]]
then
   (echo; echo 'eval "$(/opt/homebrew/bin/brew shellenv)"') >> "${HOME}/.zprofile"
   eval "$(/opt/homebrew/bin/brew shellenv)"
else
   (echo; echo 'eval "$(/usr/local/bin/brew shellenv)"') >> "${HOME}/.zprofile"
   eval "$(/usr/local/bin/brew shellenv)"
fi

[strombringer]

I ran into a similar issue (dockutils are not working with the dock role).

I've installed brew manually on the Mac, including setting the eval "$(/opt/homebrew/bin/brew shellenv)" line in ~/.zprofile (as per instructions from installing brew).

Running a playbook remotely with the dock role fails with this error:

  msg:
    changed: false
    cmd: dockutil --find 'App Store'
    failed: false
    failed_when_result: false
    msg: '[Errno 2] No such file or directory: b''dockutil'''
    rc: 2
    stderr: ''
    stderr_lines: []
    stdout: ''
    stdout_lines: []

My workaround:

Adding the homebrew paths manually to the PATH variable:
(Thanks @Kylmakalle for the link)

  environment:
    PATH: "/opt/homebrew/bin:/opt/homebrew/sbin:{{ ansible_env.PATH }}"

[geerlingguy]

Hmm... separately, on one Mac I run, which I just upgraded to Sequoia, I'm now getting:

TASK [geerlingguy.mac.dock : Install dockutil.] ************************************************************************
fatal: [127.0.0.1]: FAILED! => changed=false 
  msg: |-
    ==> Tapping hpedrorodrigues/tools
    Cloning into '/opt/homebrew/Homebrew/Library/Taps/hpedrorodrigues/homebrew-tools'...
    Tapped 2 formulae (17 files, 36.4KB).
    Warning: Cask 'dockutil' is unavailable: '/opt/homebrew/Homebrew/Library/Taps/hpedrorodrigues/homebrew-tools/Casks/dockutil.rb' does not exist.

I tried:

brew untap hpedrorodrigues/tools
brew uninstall dockutil
brew uninstall --cask dockutil

As per kcrawford/dockutil#127 (comment) — but that doesn't seem to work.

The same task runs fine on my other Macs (which were clean installs of Sequoia...).

[geerlingguy]

And... my problem was just a missing symlink. I had a really, really old version of the geerlingguy.mac collection on this Mac. Oops!

[stale]

This issue has been marked 'stale' due to lack of recent activity. If there is no further activity, the issue will be closed in another 30 days. Thank you for your contribution!

Please read this blog post to see the reasons why I mark issues as stale.

[Kylmakalle]

bump

[stale]

This issue is no longer marked for closure.

[stale]

This issue has been marked 'stale' due to lack of recent activity. If there is no further activity, the issue will be closed in another 30 days. Thank you for your contribution!

Please read this blog post to see the reasons why I mark issues as stale.