diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 419e2e3ce2..bdce78a74b 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -11,8 +11,8 @@ GEM
       public_suffix (>= 2.0.2, < 5.0)
     ast (2.4.2)
     bindata (2.4.10)
-    bootsnap (1.9.4)
-      msgpack (~> 1.0)
+    bootsnap (1.10.1)
+      msgpack (~> 1.2)
     byebug (11.1.3)
     coderay (1.1.3)
     commander (4.6.0)
diff --git a/Library/Homebrew/sorbet/rbi/gems/bootsnap@1.9.4.rbi b/Library/Homebrew/sorbet/rbi/gems/bootsnap@1.10.1.rbi
similarity index 93%
rename from Library/Homebrew/sorbet/rbi/gems/bootsnap@1.9.4.rbi
rename to Library/Homebrew/sorbet/rbi/gems/bootsnap@1.10.1.rbi
index 1066bdf797..40e5ddd2f0 100644
--- a/Library/Homebrew/sorbet/rbi/gems/bootsnap@1.9.4.rbi
+++ b/Library/Homebrew/sorbet/rbi/gems/bootsnap@1.10.1.rbi
@@ -32,6 +32,7 @@ end
 
 class Bootsnap::CompileCache::Error < ::StandardError; end
 class Bootsnap::CompileCache::PermissionError < ::Bootsnap::CompileCache::Error; end
+Bootsnap::CompileCache::UNCOMPILABLE = T.let(T.unsafe(nil), BasicObject)
 
 module Bootsnap::ExplicitRequire
   class << self
@@ -72,13 +73,13 @@ class Bootsnap::LoadPathCache::Cache
 
   def dir_changed?; end
   def expand_path(feature); end
-  def maybe_append_extension(f); end
+  def maybe_append_extension(feature); end
   def now; end
   def push_paths_locked(*paths); end
-  def search_index(f, try_extensions: T.unsafe(nil)); end
+  def search_index(feature, try_extensions: T.unsafe(nil)); end
   def stale?; end
-  def try_ext(f); end
-  def try_index(f); end
+  def try_ext(feature); end
+  def try_index(feature); end
   def unshift_paths_locked(*paths); end
 end
 
@@ -134,15 +135,17 @@ class Bootsnap::LoadPathCache::FallbackScan < ::StandardError; end
 class Bootsnap::LoadPathCache::LoadedFeaturesIndex
   def initialize; end
 
+  def cursor(short); end
+  def identify(short, cursor); end
   def key?(feature); end
   def purge(feature); end
   def purge_multi(features); end
-  def register(short, long = T.unsafe(nil)); end
+  def register(short, long); end
 
   private
 
-  def extension_elidable?(f); end
-  def strip_extension_if_elidable(f); end
+  def extension_elidable?(feature); end
+  def strip_extension_if_elidable(feature); end
 end
 
 Bootsnap::LoadPathCache::LoadedFeaturesIndex::STRIP_EXTENSION = T.let(T.unsafe(nil), Regexp)
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index bb93d365ff..51cdd30365 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -15,8 +15,8 @@ $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/ast-2.4.2/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/bindata-2.4.10/lib"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/extensions/x86_64-darwin-14/2.6.0-static/msgpack-1.4.2"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/msgpack-1.4.2/lib"
-$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/extensions/x86_64-darwin-14/2.6.0-static/bootsnap-1.9.4"
-$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/bootsnap-1.9.4/lib"
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/extensions/x86_64-darwin-14/2.6.0-static/bootsnap-1.10.1"
+$:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/bootsnap-1.10.1/lib"
 $:.unshift "#{path}/"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/extensions/x86_64-darwin-14/2.6.0-static/byebug-11.1.3"
 $:.unshift "#{path}/../#{ruby_engine}/#{ruby_version}/gems/byebug-11.1.3/lib"