diff --git a/letsencrypt-auto-source/letsencrypt-auto b/letsencrypt-auto-source/letsencrypt-auto
index 23a9d93f0..fc534f1ba 100755
--- a/letsencrypt-auto-source/letsencrypt-auto
+++ b/letsencrypt-auto-source/letsencrypt-auto
@@ -363,8 +363,8 @@ BootstrapMac() {
       brew install dialog
   fi
 
-  if ! hash pip 2>/dev/null; then
-      echo "pip not installed.\nInstalling python from Homebrew..."
+  if [ -z "$(brew list --versions python)" ]; then
+      echo "python not installed.\nInstalling python from Homebrew..."
       brew install python
   fi
 
diff --git a/letsencrypt-auto-source/pieces/bootstrappers/mac.sh b/letsencrypt-auto-source/pieces/bootstrappers/mac.sh
index 23c12eec3..4bdf34116 100755
--- a/letsencrypt-auto-source/pieces/bootstrappers/mac.sh
+++ b/letsencrypt-auto-source/pieces/bootstrappers/mac.sh
@@ -14,8 +14,8 @@ BootstrapMac() {
       brew install dialog
   fi
 
-  if ! hash pip 2>/dev/null; then
-      echo "pip not installed.\nInstalling python from Homebrew..."
+  if [ -z "$(brew list --versions python)" ]; then
+      echo "python not installed.\nInstalling python from Homebrew..."
       brew install python
   fi