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 24a4c407..0b05ab1a 100644
--- a/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
+++ b/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
@@ -57,6 +57,7 @@ if [ -d /Applications ] && [ -d /Library ] && [ -z "$NO_RESTART" ]; then
   if command -v gtimeout > /dev/null; then
     # Allow 8 minutes for system updates
     logg info 'Ensuring system software is upgraded (timing out after 50 minutes if system upgrade fails)'
+    sudo softwareupdate -i -a -R
     gtimeout 3000 sudo softwareupdate -i -a -R || logg warn 'The system update command timed out after 50 minutes'
   else
     # If gtimeout is unavailable, then attempt system upgrade without a timeout (which usually works on fresh systems)