diff --git a/Library/Homebrew/.ruby-version b/Library/Homebrew/.ruby-version
index 619b537668..a0891f563f 100644
--- a/Library/Homebrew/.ruby-version
+++ b/Library/Homebrew/.ruby-version
@@ -1 +1 @@
-3.3.3
+3.3.4
diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index e9e7c45ea0..0e317ea7a8 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -193,7 +193,7 @@ DEPENDENCIES
   yard-sorbet
 
 RUBY VERSION
-   ruby 3.3.3p89
+   ruby 3.3.4p94
 
 BUNDLED WITH
    2.5.11
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
 }
diff --git a/Library/Homebrew/vendor/portable-ruby-arm64-darwin b/Library/Homebrew/vendor/portable-ruby-arm64-darwin
index 931624f90a..ea83e9cd62 100644
--- a/Library/Homebrew/vendor/portable-ruby-arm64-darwin
+++ b/Library/Homebrew/vendor/portable-ruby-arm64-darwin
@@ -1,2 +1,2 @@
 ruby_TAG=arm64_big_sur
-ruby_SHA=49847c7a13f7094b211f6d0025900dd23716be07dac894a3d6941d7696296306
+ruby_SHA=1e64d7393d6bed090ebd892514457a10a2066682693eaade7d4a25568fa35312
diff --git a/Library/Homebrew/vendor/portable-ruby-version b/Library/Homebrew/vendor/portable-ruby-version
index 619b537668..a0891f563f 100644
--- a/Library/Homebrew/vendor/portable-ruby-version
+++ b/Library/Homebrew/vendor/portable-ruby-version
@@ -1 +1 @@
-3.3.3
+3.3.4
diff --git a/Library/Homebrew/vendor/portable-ruby-x86_64-darwin b/Library/Homebrew/vendor/portable-ruby-x86_64-darwin
index 5121655b98..2df32a7972 100644
--- a/Library/Homebrew/vendor/portable-ruby-x86_64-darwin
+++ b/Library/Homebrew/vendor/portable-ruby-x86_64-darwin
@@ -1,2 +1,2 @@
 ruby_TAG=el_capitan
-ruby_SHA=a5ef040e054444a0eb2cbcc1032fed14702dfbe2e55b25e609f3ce643f23c4ee
+ruby_SHA=a37578bcc3b57e02bcf72ad853ee493ebf6f042755c4eb922c6cb8c1a905b807
diff --git a/Library/Homebrew/vendor/portable-ruby-x86_64-linux b/Library/Homebrew/vendor/portable-ruby-x86_64-linux
index 71c4c4b928..8ec8bcb7a9 100644
--- a/Library/Homebrew/vendor/portable-ruby-x86_64-linux
+++ b/Library/Homebrew/vendor/portable-ruby-x86_64-linux
@@ -1,2 +1,2 @@
 ruby_TAG=x86_64_linux
-ruby_SHA=40a1dbc25bb1a8bbdf0bba53d3f16c45416be12d4c6d48b4530f90b2a77d64ce
+ruby_SHA=44a5a8e4c5e4f74a346e50232c13b2ec54a72d8cb5d8ebc6965a197eefc9b03f