diff --git a/scripts/package/update_all b/scripts/package/update_all
index 9a71970..cbdc128 100755
--- a/scripts/package/update_all
+++ b/scripts/package/update_all
@@ -22,10 +22,10 @@ brew outdated | xargs -n1 brew upgrade
 
 echo ''
 echo '🍻 Updating Brew Cask apps'
-OUTDATED_CASKS=$(brew cask outdated)
+OUTDATED_CASKS=$(brew outdated --cask --greedy --quiet)
 
 if [ -n "$OUTDATED_CASKS" ]; then
-  echo "$OUTDATED_CASKS" | grep -v real-vnc | xargs -n1 brew cask install --force
+  echo "$OUTDATED_CASKS" | grep -v real-vnc | xargs -n1 brew install --cask --force
   echo '✅  Casks updated'
 else
   echo '✅  Casks already up-to-date'
@@ -61,7 +61,7 @@ if [ "${1-none}" == "--all" ]; then
 
   echo ''
   echo '🐍 Updating Pip (Python)'
-  pip freeze --local | grep -v '^\-e' | cut -d = -f 1 | xargs -n1 pip install -U
+  pip list --outdated --format=freeze | grep -v '^\-e' | cut -d = -f 1 | xargs -n1 pip install -U
 
   echo ''
   echo '♦️  Updating gem (Ruby)'