From c6c40e17909411bfe9da8ad6995dacb3e0403758 Mon Sep 17 00:00:00 2001
From: Brian Zalewski <59970525+ProfessorManhattan@users.noreply.github.com>
Date: Thu, 15 Jun 2023 02:40:58 +0000
Subject: [PATCH] Latest

---
 .../universal/run_before_01-system-homebrew.sh.tmpl  | 12 +++++++++++-
 1 file changed, 11 insertions(+), 1 deletion(-)

diff --git a/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl b/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
index 5bf9fc24..8307e9bc 100644
--- a/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
+++ b/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
@@ -16,11 +16,21 @@
 
 ### System upgrade on macOS
 if [ -d /Applications ] && [ -d /Library ]; then
-  sudo softwareupdate -i -a
+  if command -v gtimeout > /dev/null; then
+    # Allow 8 minutes for system updates
+    logg info 'Ensuring system software is upgraded (timing out after 8 minutes if system upgrade fails)'
+    sudo gtimeout 480 softwareupdate -i -a || logg warn 'The system update command timed out after 8 minutes'
+  else
+    # If gtimeout is unavailable, then attempt system upgrade without a timeout (which usually works on fresh systems)
+    logg info 'Applying OS upgrades (if available)'
+    sudo softwareupdate -i -a || logg error 'Failed to perform a system update via `sudo softwareupdate -i -a`'
+  fi
+  logg info 'If system updates were downloaded / installed, a reboot might be required.'
 fi
 
 ### Install Xcode CLI tools on macOS
 if [ -d /Applications ] && [ -d /Library ]; then
+  logg info 'Ensuring xcode-select is installed for developer tools'
   xcode-select -p >/dev/null 2>&1 || sudo xcode-select --install
 fi