diff --git a/home/.chezmoiscripts/universal/run_before_02-homebrew.sh.tmpl b/home/.chezmoiscripts/universal/run_before_02-homebrew.sh.tmpl
index 2f769639..5c500508 100644
--- a/home/.chezmoiscripts/universal/run_before_02-homebrew.sh.tmpl
+++ b/home/.chezmoiscripts/universal/run_before_02-homebrew.sh.tmpl
@@ -132,6 +132,7 @@ upgradeDarwin() {
 
     ### Run upgrade process
     logg info 'Applying OS upgrades (if available)'
+    logg info 'This may take awhile..'
     expect -c "set timeout -1
     spawn sudo softwareupdate -i -a --agree-to-license
     expect \"Password:\"
@@ -165,10 +166,6 @@ upgradeDarwin() {
 
       ### Reboot
       logg info 'Reboot required' && exit 140
-      # gtimeout 60 osascript -e 'tell application "Finder" to shut down' || OSASCRIPT_EXIT_CODE=$?
-      # if [ -n "$OSASCRIPT_EXIT_CODE" ]; then
-      #   logg info 'Reboot required and failed to gracefully shutdown within 1 minute, so forcing reboot' && sudo sh -c 'shutdown -r now'
-      # fi
     else
       logg info 'No reboot required for softwareupdate'
     fi
diff --git a/home/dot_config/shell/profile.sh.tmpl b/home/dot_config/shell/profile.sh.tmpl
index 9acbdf2a..3ca32c02 100644
--- a/home/dot_config/shell/profile.sh.tmpl
+++ b/home/dot_config/shell/profile.sh.tmpl
@@ -97,6 +97,11 @@ if [ "$BASH_SUPPORT" = 'true' ]; then
   if [ -f "${XDG_CONFIG_HOME:-$HOME/.config}/shell/motd.sh" ]; then
     . "${XDG_CONFIG_HOME:-$HOME/.config}/shell/motd.sh"
   fi
+
+  ### SUDO_ASKPASS
+  if [ -d /Applications ] && [ -d /System ]; then
+    SUDO_ASKPASS="$HOME/.local/bin/sudo-askpass"
+  fi
 fi
 
 ### Cargo
diff --git a/home/dot_local/bin/executable_sudo-askpass b/home/dot_local/bin/executable_sudo-askpass
new file mode 100644
index 00000000..2c6b21a1
--- /dev/null
+++ b/home/dot_local/bin/executable_sudo-askpass
@@ -0,0 +1,17 @@
+#!/usr/bin/env bash
+# @file Sudo Password Helper
+# @brief Integrates sudo password entry with native system dialogs for `SUDO_ASKPASS`
+# @description
+#   Many programs allow you to define the `SUDO_ASKPASS` environment variable to handle passing in
+#   sudo privileges. For more details, check out [this StackOverflow post](https://stackoverflow.com/questions/12608293/how-to-setup-a-sudo-askpass-environment-variable).
+
+if [ -z "$SUDO_PASSWORD" ]; then
+  if [ -d /Applications ] && [ -d /System ]; then
+    ### macOS
+    SUDO_PASSWORD="$(osascript -e 'Tell application "System Events" to display dialog "Administrator Password:" default answer "" with hidden answer' -e 'text returned of result' 2>/dev/null)"
+  else
+    ### Linux
+    SUDO_PASSWORD="TODO"
+  fi
+fi
+echo "$SUDO_PASSWORD"