diff --git a/.gitignore b/.gitignore
index b89793014d141e..99eef04e54a823 100644
--- a/.gitignore
+++ b/.gitignore
@@ -63,7 +63,6 @@
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/*/
-!**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/enumerable.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/file/atomic.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/hash/deep_merge.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/hash/deep_transform_values.rb
diff --git a/Library/Homebrew/extend/enumerable.rb b/Library/Homebrew/extend/enumerable.rb
index d5a0ab9012b081..4c3eb14ecbc396 100644
--- a/Library/Homebrew/extend/enumerable.rb
+++ b/Library/Homebrew/extend/enumerable.rb
@@ -1,3 +1,4 @@
+# typed: strict
 # frozen_string_literal: true
 
 module Enumerable
@@ -9,21 +10,20 @@ module Enumerable
   #
   #   people.index_by { |person| "#{person.first_name} #{person.last_name}" }
   #   # => { "Chade- Fowlersburg-e" => <Person ...>, "David Heinemeier Hansson" => <Person ...>, ...}
-  def index_by
-    if block_given?
+  def index_by(&block)
+    if block
       result = {}
       each { |elem| result[yield(elem)] = elem }
       result
     else
-      to_enum(:index_by) { size if respond_to?(:size) }
+      T.unsafe(self).to_enum(:index_by) { T.unsafe(self).size if respond_to?(:size) }
     end
   end
 
   # The negative of the <tt>Enumerable#include?</tt>. Returns +true+ if the
   # collection does not include the object.
-  def exclude?(object)
-    !include?(object)
-  end
+  sig { params(object: T.untyped).returns(T::Boolean) }
+  def exclude?(object) = !include?(object)
 
   # Returns a new +Array+ without the blank items.
   # Uses Object#blank? for determining if an item is blank.
@@ -38,14 +38,11 @@ def exclude?(object)
   #
   #   { a: "", b: 1, c: nil, d: [], e: false, f: true }.compact_blank
   #   # => { b: 1, f: true }
-  def compact_blank
-    reject(&:blank?)
-  end
+  sig { returns(T.self_type) }
+  def compact_blank = T.unsafe(self).reject(&:blank?)
 end
 
 class Hash
   # Hash#reject has its own definition, so this needs one too.
-  def compact_blank # :nodoc:
-    reject { |_k, v| v.blank? }
-  end
+  def compact_blank = reject { T.unsafe(_2).blank? }
 end
diff --git a/Library/Homebrew/extend/enumerable.rbi b/Library/Homebrew/extend/enumerable.rbi
new file mode 100644
index 00000000000000..a95b0bf4bb4fa4
--- /dev/null
+++ b/Library/Homebrew/extend/enumerable.rbi
@@ -0,0 +1,17 @@
+# typed: strict
+
+module Enumerable
+  requires_ancestor { Object }
+
+  sig {
+    type_parameters(:key).params(
+      block: T.nilable(T.proc.params(o: Enumerable::Elem).returns(T.type_parameter(:key))),
+    ).returns(T::Hash[T.type_parameter(:key), Enumerable::Elem])
+  }
+  def index_by(&block); end
+end
+
+class Hash
+  sig { returns(T::Hash[Hash::K, Hash::V]) }
+  def compact_blank; end
+end
diff --git a/Library/Homebrew/global.rb b/Library/Homebrew/global.rb
index 077d7cce035d02..e3e866a459f579 100644
--- a/Library/Homebrew/global.rb
+++ b/Library/Homebrew/global.rb
@@ -10,7 +10,6 @@
 require "forwardable"
 require "set"
 
-require "active_support/core_ext/enumerable"
 require "active_support/core_ext/file/atomic"
 require "active_support/core_ext/hash/deep_merge"
 require "active_support/core_ext/hash/keys"
@@ -68,6 +67,7 @@
 
 require "extend/array"
 require "extend/blank"
+require "extend/enumerable"
 require "extend/string"
 require "env_config"
 require "macos_version"
diff --git a/Library/Homebrew/vendor/bundle/ruby/3.1.0/gems/activesupport-6.1.7.6/lib/active_support/core_ext/enumerable.rb b/Library/Homebrew/vendor/bundle/ruby/3.1.0/gems/activesupport-6.1.7.6/lib/active_support/core_ext/enumerable.rb
deleted file mode 100644
index 97c918a71f89e5..00000000000000
--- a/Library/Homebrew/vendor/bundle/ruby/3.1.0/gems/activesupport-6.1.7.6/lib/active_support/core_ext/enumerable.rb
+++ /dev/null
@@ -1,260 +0,0 @@
-# frozen_string_literal: true
-
-module Enumerable
-  INDEX_WITH_DEFAULT = Object.new
-  private_constant :INDEX_WITH_DEFAULT
-
-  # Enumerable#sum was added in Ruby 2.4, but it only works with Numeric elements
-  # when we omit an identity.
-
-  # :stopdoc:
-
-  # We can't use Refinements here because Refinements with Module which will be prepended
-  # doesn't work well https://bugs.ruby-lang.org/issues/13446
-  alias :_original_sum_with_required_identity :sum
-  private :_original_sum_with_required_identity
-
-  # :startdoc:
-
-  # Calculates a sum from the elements.
-  #
-  #  payments.sum { |p| p.price * p.tax_rate }
-  #  payments.sum(&:price)
-  #
-  # The latter is a shortcut for:
-  #
-  #  payments.inject(0) { |sum, p| sum + p.price }
-  #
-  # It can also calculate the sum without the use of a block.
-  #
-  #  [5, 15, 10].sum # => 30
-  #  ['foo', 'bar'].sum # => "foobar"
-  #  [[1, 2], [3, 1, 5]].sum # => [1, 2, 3, 1, 5]
-  #
-  # The default sum of an empty list is zero. You can override this default:
-  #
-  #  [].sum(Payment.new(0)) { |i| i.amount } # => Payment.new(0)
-  def sum(identity = nil, &block)
-    if identity
-      _original_sum_with_required_identity(identity, &block)
-    elsif block_given?
-      map(&block).sum(identity)
-    else
-      inject(:+) || 0
-    end
-  end
-
-  # Convert an enumerable to a hash, using the block result as the key and the
-  # element as the value.
-  #
-  #   people.index_by(&:login)
-  #   # => { "nextangle" => <Person ...>, "chade-" => <Person ...>, ...}
-  #
-  #   people.index_by { |person| "#{person.first_name} #{person.last_name}" }
-  #   # => { "Chade- Fowlersburg-e" => <Person ...>, "David Heinemeier Hansson" => <Person ...>, ...}
-  def index_by
-    if block_given?
-      result = {}
-      each { |elem| result[yield(elem)] = elem }
-      result
-    else
-      to_enum(:index_by) { size if respond_to?(:size) }
-    end
-  end
-
-  # Convert an enumerable to a hash, using the element as the key and the block
-  # result as the value.
-  #
-  #   post = Post.new(title: "hey there", body: "what's up?")
-  #
-  #   %i( title body ).index_with { |attr_name| post.public_send(attr_name) }
-  #   # => { title: "hey there", body: "what's up?" }
-  #
-  # If an argument is passed instead of a block, it will be used as the value
-  # for all elements:
-  #
-  #   %i( created_at updated_at ).index_with(Time.now)
-  #   # => { created_at: 2020-03-09 22:31:47, updated_at: 2020-03-09 22:31:47 }
-  def index_with(default = INDEX_WITH_DEFAULT)
-    if block_given?
-      result = {}
-      each { |elem| result[elem] = yield(elem) }
-      result
-    elsif default != INDEX_WITH_DEFAULT
-      result = {}
-      each { |elem| result[elem] = default }
-      result
-    else
-      to_enum(:index_with) { size if respond_to?(:size) }
-    end
-  end
-
-  # Returns +true+ if the enumerable has more than 1 element. Functionally
-  # equivalent to <tt>enum.to_a.size > 1</tt>. Can be called with a block too,
-  # much like any?, so <tt>people.many? { |p| p.age > 26 }</tt> returns +true+
-  # if more than one person is over 26.
-  def many?
-    cnt = 0
-    if block_given?
-      any? do |element|
-        cnt += 1 if yield element
-        cnt > 1
-      end
-    else
-      any? { (cnt += 1) > 1 }
-    end
-  end
-
-  # Returns a new array that includes the passed elements.
-  #
-  #   [ 1, 2, 3 ].including(4, 5)
-  #   # => [ 1, 2, 3, 4, 5 ]
-  #
-  #   ["David", "Rafael"].including %w[ Aaron Todd ]
-  #   # => ["David", "Rafael", "Aaron", "Todd"]
-  def including(*elements)
-    to_a.including(*elements)
-  end
-
-  # The negative of the <tt>Enumerable#include?</tt>. Returns +true+ if the
-  # collection does not include the object.
-  def exclude?(object)
-    !include?(object)
-  end
-
-  # Returns a copy of the enumerable excluding the specified elements.
-  #
-  #   ["David", "Rafael", "Aaron", "Todd"].excluding "Aaron", "Todd"
-  #   # => ["David", "Rafael"]
-  #
-  #   ["David", "Rafael", "Aaron", "Todd"].excluding %w[ Aaron Todd ]
-  #   # => ["David", "Rafael"]
-  #
-  #   {foo: 1, bar: 2, baz: 3}.excluding :bar
-  #   # => {foo: 1, baz: 3}
-  def excluding(*elements)
-    elements.flatten!(1)
-    reject { |element| elements.include?(element) }
-  end
-
-  # Alias for #excluding.
-  def without(*elements)
-    excluding(*elements)
-  end
-
-  # Extract the given key from each element in the enumerable.
-  #
-  #   [{ name: "David" }, { name: "Rafael" }, { name: "Aaron" }].pluck(:name)
-  #   # => ["David", "Rafael", "Aaron"]
-  #
-  #   [{ id: 1, name: "David" }, { id: 2, name: "Rafael" }].pluck(:id, :name)
-  #   # => [[1, "David"], [2, "Rafael"]]
-  def pluck(*keys)
-    if keys.many?
-      map { |element| keys.map { |key| element[key] } }
-    else
-      key = keys.first
-      map { |element| element[key] }
-    end
-  end
-
-  # Extract the given key from the first element in the enumerable.
-  #
-  #   [{ name: "David" }, { name: "Rafael" }, { name: "Aaron" }].pick(:name)
-  #   # => "David"
-  #
-  #   [{ id: 1, name: "David" }, { id: 2, name: "Rafael" }].pick(:id, :name)
-  #   # => [1, "David"]
-  def pick(*keys)
-    return if none?
-
-    if keys.many?
-      keys.map { |key| first[key] }
-    else
-      first[keys.first]
-    end
-  end
-
-  # Returns a new +Array+ without the blank items.
-  # Uses Object#blank? for determining if an item is blank.
-  #
-  #    [1, "", nil, 2, " ", [], {}, false, true].compact_blank
-  #    # =>  [1, 2, true]
-  #
-  #    Set.new([nil, "", 1, 2])
-  #    # => [2, 1] (or [1, 2])
-  #
-  # When called on a +Hash+, returns a new +Hash+ without the blank values.
-  #
-  #    { a: "", b: 1, c: nil, d: [], e: false, f: true }.compact_blank
-  #    #=> { b: 1, f: true }
-  def compact_blank
-    reject(&:blank?)
-  end
-end
-
-class Hash
-  # Hash#reject has its own definition, so this needs one too.
-  def compact_blank #:nodoc:
-    reject { |_k, v| v.blank? }
-  end
-
-  # Removes all blank values from the +Hash+ in place and returns self.
-  # Uses Object#blank? for determining if a value is blank.
-  #
-  #    h = { a: "", b: 1, c: nil, d: [], e: false, f: true }
-  #    h.compact_blank!
-  #    # => { b: 1, f: true }
-  def compact_blank!
-    # use delete_if rather than reject! because it always returns self even if nothing changed
-    delete_if { |_k, v| v.blank? }
-  end
-end
-
-class Range #:nodoc:
-  # Optimize range sum to use arithmetic progression if a block is not given and
-  # we have a range of numeric values.
-  def sum(identity = nil)
-    if block_given? || !(first.is_a?(Integer) && last.is_a?(Integer))
-      super
-    else
-      actual_last = exclude_end? ? (last - 1) : last
-      if actual_last >= first
-        sum = identity || 0
-        sum + (actual_last - first + 1) * (actual_last + first) / 2
-      else
-        identity || 0
-      end
-    end
-  end
-end
-
-# Using Refinements here in order not to expose our internal method
-using Module.new {
-  refine Array do
-    alias :orig_sum :sum
-  end
-}
-
-class Array #:nodoc:
-  # Array#sum was added in Ruby 2.4 but it only works with Numeric elements.
-  def sum(init = nil, &block)
-    if init.is_a?(Numeric) || first.is_a?(Numeric)
-      init ||= 0
-      orig_sum(init, &block)
-    else
-      super
-    end
-  end
-
-  # Removes all blank elements from the +Array+ in place and returns self.
-  # Uses Object#blank? for determining if an item is blank.
-  #
-  #    a = [1, "", nil, 2, " ", [], {}, false, true]
-  #    a.compact_blank!
-  #    # =>  [1, 2, true]
-  def compact_blank!
-    # use delete_if rather than reject! because it always returns self even if nothing changed
-    delete_if(&:blank?)
-  end
-end