diff --git a/Library/Homebrew/cmd/vendor-install.sh b/Library/Homebrew/cmd/vendor-install.sh
index ab6b4afffc..4a47df700c 100644
--- a/Library/Homebrew/cmd/vendor-install.sh
+++ b/Library/Homebrew/cmd/vendor-install.sh
@@ -365,4 +365,11 @@ homebrew-vendor-install() {
   lock "vendor-install-${VENDOR_NAME}"
   fetch
   install
+
+  # Bootsnap needs cleaned up on a new Ruby version.
+  # It's cleaned up by every `brew cleanup` run anyway so not a big deal to do it here, too.
+  if [[ "${VENDOR_NAME}" == "ruby" ]]
+  then
+    rm -rf "${HOMEBREW_CACHE}/bootsnap"
+  fi
 }