diff --git a/Library/Homebrew/cleanup.rb b/Library/Homebrew/cleanup.rb
index 0e5102ddb8..b6cc9f836a 100644
--- a/Library/Homebrew/cleanup.rb
+++ b/Library/Homebrew/cleanup.rb
@@ -558,7 +558,7 @@ module Homebrew
       return unless bootsnap.directory?
 
       bootsnap.each_child do |subdir|
-        cleanup_path(subdir) { FileUtils.rm_r(subdir) } if subdir.basename.to_s != Homebrew.bootsnap_key
+        cleanup_path(subdir) { FileUtils.rm_r(subdir) } if subdir.basename.to_s != Homebrew::Bootsnap.key
       end
     end
 
diff --git a/Library/Homebrew/standalone/init.rbi b/Library/Homebrew/standalone/init.rbi
new file mode 100644
index 0000000000..95b05bc303
--- /dev/null
+++ b/Library/Homebrew/standalone/init.rbi
@@ -0,0 +1,3 @@
+# typed: strict
+
+HOMEBREW_USING_PORTABLE_RUBY = T.let(false, T::Boolean)
diff --git a/Library/Homebrew/startup/bootsnap.rb b/Library/Homebrew/startup/bootsnap.rb
index 01a9a662ea..375600fb10 100644
--- a/Library/Homebrew/startup/bootsnap.rb
+++ b/Library/Homebrew/startup/bootsnap.rb
@@ -1,46 +1,67 @@
 # typed: true
 # frozen_string_literal: true
 
-homebrew_bootsnap_enabled = HOMEBREW_USING_PORTABLE_RUBY &&
-                            ENV["HOMEBREW_NO_BOOTSNAP"].nil? &&
-                            !ENV["HOMEBREW_BOOTSNAP"].nil?
-
 module Homebrew
-  def self.bootsnap_key
-    @bootsnap_key ||= begin
-      require "digest/sha2"
+  module Bootsnap
+    def self.key
+      @key ||= begin
+        require "digest/sha2"
 
-      checksum = Digest::SHA256.new
-      checksum << RUBY_VERSION
-      checksum << RUBY_PLATFORM
-      checksum << Dir.children(File.join(Gem.paths.path, "gems")).join(",")
+        checksum = Digest::SHA256.new
+        checksum << RUBY_VERSION
+        checksum << RUBY_PLATFORM
+        checksum << Dir.children(File.join(Gem.paths.path, "gems")).join(",")
 
-      checksum.hexdigest
+        checksum.hexdigest
+      end
+    end
+
+    private_class_method def self.cache_dir
+      cache = ENV.fetch("HOMEBREW_CACHE", nil) || ENV.fetch("HOMEBREW_DEFAULT_CACHE", nil)
+      raise "Needs HOMEBREW_CACHE or HOMEBREW_DEFAULT_CACHE!" if cache.nil? || cache.empty?
+
+      File.join(cache, "bootsnap", key)
+    end
+
+    private_class_method def self.ignore_directories
+      # We never do `require "vendor/bundle/ruby/..."` or `require "vendor/portable-ruby/..."`,
+      # so let's slim the cache a bit by excluding them.
+      # Note that gems within `bundle/ruby` will still be cached - these are when directory walking down from above.
+      [
+        (HOMEBREW_LIBRARY_PATH/"vendor/bundle/ruby").to_s,
+        (HOMEBREW_LIBRARY_PATH/"vendor/portable-ruby").to_s,
+      ]
+    end
+
+    private_class_method def self.enabled?
+      HOMEBREW_USING_PORTABLE_RUBY && ENV["HOMEBREW_NO_BOOTSNAP"].nil? && !ENV["HOMEBREW_BOOTSNAP"].nil?
+    end
+
+    def self.load!(compile_cache: true)
+      return unless enabled?
+
+      require "bootsnap"
+
+      ::Bootsnap.setup(
+        cache_dir:,
+        ignore_directories:,
+        load_path_cache:    true,
+        compile_cache_iseq: compile_cache,
+        compile_cache_yaml: compile_cache,
+        compile_cache_json: compile_cache,
+      )
+    end
+
+    def self.reset!
+      return unless enabled?
+
+      ::Bootsnap.unload_cache!
+      @key = nil
+
+      # The compile cache doesn't get unloaded so we don't need to load it again!
+      load!(compile_cache: false)
     end
   end
 end
 
-if homebrew_bootsnap_enabled
-  require "bootsnap"
-
-  cache = ENV.fetch("HOMEBREW_CACHE", nil) || ENV.fetch("HOMEBREW_DEFAULT_CACHE", nil)
-  raise "Needs HOMEBREW_CACHE or HOMEBREW_DEFAULT_CACHE!" if cache.nil? || cache.empty?
-
-  cache = File.join(cache, "bootsnap", Homebrew.bootsnap_key)
-
-  # We never do `require "vendor/bundle/ruby/..."` or `require "vendor/portable-ruby/..."`,
-  # so let's slim the cache a bit by excluding them.
-  # Note that gems within `bundle/ruby` will still be cached - these are when directory walking down from above.
-  ignore_directories = [
-    (HOMEBREW_LIBRARY_PATH/"vendor/bundle/ruby").to_s,
-    (HOMEBREW_LIBRARY_PATH/"vendor/portable-ruby").to_s,
-  ]
-
-  Bootsnap.setup(
-    cache_dir:          cache,
-    ignore_directories:,
-    load_path_cache:    true,
-    compile_cache_iseq: true,
-    compile_cache_yaml: true,
-  )
-end
+Homebrew::Bootsnap.load!
diff --git a/Library/Homebrew/startup/bootsnap.rbi b/Library/Homebrew/startup/bootsnap.rbi
index 3f42e1837d..d71df2d278 100644
--- a/Library/Homebrew/startup/bootsnap.rbi
+++ b/Library/Homebrew/startup/bootsnap.rbi
@@ -1,8 +1,25 @@
 # typed: strict
 
 module Homebrew
-  sig { returns(String) }
-  def self.bootsnap_key; end
+  module Bootsnap
+    sig { returns(String) }
+    def self.key; end
+
+    sig { returns(String) }
+    private_class_method def self.cache_dir; end
+
+    sig { returns(T::Array[String]) }
+    private_class_method def self.ignore_directories; end
+
+    sig { returns(T::Boolean) }
+    private_class_method def self.enabled?; end
+
+    sig { params(compile_cache: T::Boolean).void }
+    def self.load!(compile_cache: true); end
+
+    sig { void }
+    def self.reset!; end
+  end
 end
 
 module Bootsnap
@@ -29,5 +46,9 @@ module Bootsnap
     compile_cache_iseq: true,
     compile_cache_yaml: true,
     compile_cache_json: true
-  ); end
+  )
+  end
+
+  sig { void }
+  def self.unload_cache!; end
 end
diff --git a/Library/Homebrew/utils/gems.rb b/Library/Homebrew/utils/gems.rb
index d4c2fa20dd..7559aff210 100644
--- a/Library/Homebrew/utils/gems.rb
+++ b/Library/Homebrew/utils/gems.rb
@@ -303,6 +303,7 @@ module Homebrew
           exec bundle, "install", out: :err
         end)
         if $CHILD_STATUS.success?
+          Homebrew::Bootsnap.reset! if defined?(Homebrew::Bootsnap) # Gem install can run before Bootsnap loads
           true
         else
           message = <<~EOS