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 c91f20ae..a3df3414 100644
--- a/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
+++ b/home/.chezmoiscripts/universal/run_before_01-system-homebrew.sh.tmpl
@@ -30,17 +30,19 @@
 
 ### System upgrade on macOS
 # Note: If a shutdown is required and the `softwareupdate` command restart command does not work then `m shutdown -f` might be useful or `m restart -f`
+# Do you want to terminate running processes in this window?
+# Closing this window will terminate the running processes: softwareupdate, sudo
 if [ -d /Applications ] && [ -d /Library ] && [ -z "$NO_RESTART" ]; then
   if [ ! -f "$HOME/.zshrc" ] || ! cat "$HOME/.zshrc" | grep '# TEMPORARY FOR INSTALL DOCTOR MACOS' > /dev/null; then
     echo 'bash <(curl -sSL https://install.doctor/start) # TEMPORARY FOR INSTALL DOCTOR MACOS' >> "$HOME/.zshrc"
   fi
   if command -v gtimeout > /dev/null; then
     logg info 'Ensuring system software is upgraded (timing out after 50 minutes if system upgrade fails)'
-    sudo gtimeout 3000 softwareupdate -i -a -R || logg warn 'The system update command timed out after 50 minutes'
+    sudo gtimeout 3000 softwareupdate -i -a -R --agree-to-license || 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)
     logg info 'Applying OS upgrades (if available)'
-    sudo softwareupdate -i -a -R || logg error 'Failed to perform a system update via sudo softwareupdate -i -a -R'
+    sudo softwareupdate -i -a -R --agree-to-license || logg error 'Failed to perform a system update via sudo softwareupdate -i -a -R'
   fi
   logg info 'If system updates were downloaded / installed, a reboot might be required.'
   if command -v gsed > /dev/null; then