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Cade's Dotfiles

Bootstrap upgrade leaves GUI apps outdated

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Source: Troubleshooting reference

Symptom: formula upgrades complete, but VS Code, ChatGPT, or other casks remain outdated. The output says Cask upgrades deferred.

Root cause: the cask pass requires cached sudo authentication. Previously, bootstrap only checked sudo -n true and skipped every cask if it failed, even when individual apps did not need privileges. A manual sudo -v before starting was unreliable because lengthy formula upgrades could outlast the timestamp.

Confirm: inspect the bootstrap output for the deferral message and compare Homebrew’s records with the app’s own version:

Terminal window
brew outdated --cask --greedy

Auto-updating apps can have stale Homebrew receipts, so this list alone does not establish the version of the app bundle.

Fix: run the updated ~/dotfiles/bootstrap.sh upgrade from an interactive terminal. Bootstrap authenticates once and maintains the timestamp until exit. Keep DF_SUDO=auto and the desired cask/MAS upgrade gates enabled. Unattended runs without authentication report the skipped upgrades in the degradation summary. See sudo session behavior for configuration and limitations.

If the log first reports sudo credential renewal failed, the credential was lost during the run. Updated installers recheck before cask, App Store, and TeX updates and can visibly reauthenticate in an interactive terminal. The keeper preserves sudo’s error and retries without prompting. Inspect the effective policy with sudo -l if renewal repeatedly fails; do not change sudo timeout or security policy merely to suppress the warning. An unattended run still needs an interactive follow-up to complete skipped updates.