diff --git a/.gitignore b/.gitignore
index 806bde19fc..21b10a5f1e 100644
--- a/.gitignore
+++ b/.gitignore
@@ -73,7 +73,6 @@
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/object/blank.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/object/deep_dup.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/object/duplicable.rb
-!**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/object/try.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/string/exclude.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/string/filters.rb
 !**/vendor/bundle/ruby/*/gems/activesupport-*/lib/active_support/core_ext/string/indent.rb
diff --git a/Library/Homebrew/cask/artifact/artifact.rb b/Library/Homebrew/cask/artifact/artifact.rb
index 4ab625dfdf..c1d2f306b0 100644
--- a/Library/Homebrew/cask/artifact/artifact.rb
+++ b/Library/Homebrew/cask/artifact/artifact.rb
@@ -20,7 +20,7 @@ module Cask
 
         raise CaskInvalidError.new(cask.token, "No source provided for #{english_name}.") if source.blank?
 
-        unless options.try(:key?, :target)
+        unless options&.key?(:target)
           raise CaskInvalidError.new(cask.token, "#{english_name} '#{source}' requires a target.")
         end
 
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index 2bee5d03aa..a9e42cc6b3 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -300,12 +300,12 @@ on_request: true)
 
     def missing_cask_and_formula_dependencies
       cask_and_formula_dependencies.reject do |cask_or_formula|
-        installed = if cask_or_formula.respond_to?(:any_version_installed?)
-          cask_or_formula.any_version_installed?
-        else
-          cask_or_formula.try(:installed?)
+        case cask_or_formula
+        when Formula
+          cask_or_formula.any_version_installed? && cask_or_formula.optlinked?
+        when Cask
+          cask_or_formula.installed?
         end
-        installed && (cask_or_formula.respond_to?(:optlinked?) ? cask_or_formula.optlinked? : true)
       end
     end
 
diff --git a/Library/Homebrew/dev-cmd/bump.rb b/Library/Homebrew/dev-cmd/bump.rb
index 736f163441..5566675408 100644
--- a/Library/Homebrew/dev-cmd/bump.rb
+++ b/Library/Homebrew/dev-cmd/bump.rb
@@ -279,7 +279,7 @@ module Homebrew
   def retrieve_pull_requests(formula_or_cask, name, state:, version: nil)
     tap_remote_repo = formula_or_cask.tap&.remote_repo || formula_or_cask.tap&.full_name
     pull_requests = GitHub.fetch_pull_requests(name, tap_remote_repo, state: state, version: version)
-    if pull_requests.try(:any?)
+    if pull_requests&.any?
       pull_requests = pull_requests.map { |pr| "#{pr["title"]} (#{Formatter.url(pr["html_url"])})" }.join(", ")
     end
 
diff --git a/Library/Homebrew/extend/ENV/shared.rb b/Library/Homebrew/extend/ENV/shared.rb
index fb25328cf7..5bbbd4be1c 100644
--- a/Library/Homebrew/extend/ENV/shared.rb
+++ b/Library/Homebrew/extend/ENV/shared.rb
@@ -288,7 +288,7 @@ module SharedEnvExtension
     gcc_version_name = "gcc@#{version}"
 
     gcc = Formulary.factory("gcc")
-    if gcc.try(:version_suffix) == version
+    if gcc.respond_to?(:version_suffix) && T.unsafe(gcc).version_suffix == version
       gcc
     else
       Formulary.factory(gcc_version_name)
diff --git a/Library/Homebrew/formula.rb b/Library/Homebrew/formula.rb
index e7b757c5e8..0544e7d6f0 100644
--- a/Library/Homebrew/formula.rb
+++ b/Library/Homebrew/formula.rb
@@ -2351,12 +2351,17 @@ class Formula
     hsh["requirements"] = merge_spec_dependables(requirements).map do |data|
       req = data[:dependable]
       req_name = req.name.dup
-      req_name.prepend("maximum_") if req.try(:comparator) == "<="
+      req_name.prepend("maximum_") if req.respond_to?(:comparator) && req.comparator == "<="
+      req_version = if req.respond_to?(:version)
+        req.version
+      elsif req.respond_to?(:arch)
+        req.arch
+      end
       {
         "name"     => req_name,
         "cask"     => req.cask,
         "download" => req.download,
-        "version"  => req.try(:version) || req.try(:arch),
+        "version"  => req_version,
         "contexts" => req.tags,
         "specs"    => data[:specs],
       }
diff --git a/Library/Homebrew/global.rb b/Library/Homebrew/global.rb
index 3597cfe82f..487b40710e 100644
--- a/Library/Homebrew/global.rb
+++ b/Library/Homebrew/global.rb
@@ -19,7 +19,6 @@ require "active_support/core_ext/hash/deep_merge"
 require "active_support/core_ext/hash/except"
 require "active_support/core_ext/hash/keys"
 require "active_support/core_ext/object/blank"
-require "active_support/core_ext/object/try"
 require "active_support/core_ext/string/exclude"
 require "active_support/core_ext/string/filters"
 require "active_support/core_ext/string/indent"
diff --git a/Library/Homebrew/lazy_object.rb b/Library/Homebrew/lazy_object.rb
index 4dfcbdb4e6..4966f959f8 100644
--- a/Library/Homebrew/lazy_object.rb
+++ b/Library/Homebrew/lazy_object.rb
@@ -1,6 +1,8 @@
 # typed: true
 # frozen_string_literal: true
 
+require "delegate"
+
 # An object which lazily evaluates its inner block only once a method is called on it.
 #
 # @api private
diff --git a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/activesupport-6.1.7.6/lib/active_support/core_ext/object/try.rb b/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/activesupport-6.1.7.6/lib/active_support/core_ext/object/try.rb
deleted file mode 100644
index 999141a993..0000000000
--- a/Library/Homebrew/vendor/bundle/ruby/2.6.0/gems/activesupport-6.1.7.6/lib/active_support/core_ext/object/try.rb
+++ /dev/null
@@ -1,158 +0,0 @@
-# frozen_string_literal: true
-
-require "delegate"
-
-module ActiveSupport
-  module Tryable #:nodoc:
-    def try(method_name = nil, *args, &b)
-      if method_name.nil? && block_given?
-        if b.arity == 0
-          instance_eval(&b)
-        else
-          yield self
-        end
-      elsif respond_to?(method_name)
-        public_send(method_name, *args, &b)
-      end
-    end
-    ruby2_keywords(:try) if respond_to?(:ruby2_keywords, true)
-
-    def try!(method_name = nil, *args, &b)
-      if method_name.nil? && block_given?
-        if b.arity == 0
-          instance_eval(&b)
-        else
-          yield self
-        end
-      else
-        public_send(method_name, *args, &b)
-      end
-    end
-    ruby2_keywords(:try!) if respond_to?(:ruby2_keywords, true)
-  end
-end
-
-class Object
-  include ActiveSupport::Tryable
-
-  ##
-  # :method: try
-  #
-  # :call-seq:
-  #   try(*a, &b)
-  #
-  # Invokes the public method whose name goes as first argument just like
-  # +public_send+ does, except that if the receiver does not respond to it the
-  # call returns +nil+ rather than raising an exception.
-  #
-  # This method is defined to be able to write
-  #
-  #   @person.try(:name)
-  #
-  # instead of
-  #
-  #   @person.name if @person
-  #
-  # +try+ calls can be chained:
-  #
-  #   @person.try(:spouse).try(:name)
-  #
-  # instead of
-  #
-  #   @person.spouse.name if @person && @person.spouse
-  #
-  # +try+ will also return +nil+ if the receiver does not respond to the method:
-  #
-  #   @person.try(:non_existing_method) # => nil
-  #
-  # instead of
-  #
-  #   @person.non_existing_method if @person.respond_to?(:non_existing_method) # => nil
-  #
-  # +try+ returns +nil+ when called on +nil+ regardless of whether it responds
-  # to the method:
-  #
-  #   nil.try(:to_i) # => nil, rather than 0
-  #
-  # Arguments and blocks are forwarded to the method if invoked:
-  #
-  #   @posts.try(:each_slice, 2) do |a, b|
-  #     ...
-  #   end
-  #
-  # The number of arguments in the signature must match. If the object responds
-  # to the method the call is attempted and +ArgumentError+ is still raised
-  # in case of argument mismatch.
-  #
-  # If +try+ is called without arguments it yields the receiver to a given
-  # block unless it is +nil+:
-  #
-  #   @person.try do |p|
-  #     ...
-  #   end
-  #
-  # You can also call try with a block without accepting an argument, and the block
-  # will be instance_eval'ed instead:
-  #
-  #   @person.try { upcase.truncate(50) }
-  #
-  # Please also note that +try+ is defined on +Object+. Therefore, it won't work
-  # with instances of classes that do not have +Object+ among their ancestors,
-  # like direct subclasses of +BasicObject+.
-
-  ##
-  # :method: try!
-  #
-  # :call-seq:
-  #   try!(*a, &b)
-  #
-  # Same as #try, but raises a +NoMethodError+ exception if the receiver is
-  # not +nil+ and does not implement the tried method.
-  #
-  #   "a".try!(:upcase) # => "A"
-  #   nil.try!(:upcase) # => nil
-  #   123.try!(:upcase) # => NoMethodError: undefined method `upcase' for 123:Integer
-end
-
-class Delegator
-  include ActiveSupport::Tryable
-
-  ##
-  # :method: try
-  #
-  # :call-seq:
-  #   try(a*, &b)
-  #
-  # See Object#try
-
-  ##
-  # :method: try!
-  #
-  # :call-seq:
-  #   try!(a*, &b)
-  #
-  # See Object#try!
-end
-
-class NilClass
-  # Calling +try+ on +nil+ always returns +nil+.
-  # It becomes especially helpful when navigating through associations that may return +nil+.
-  #
-  #   nil.try(:name) # => nil
-  #
-  # Without +try+
-  #   @person && @person.children.any? && @person.children.first.name
-  #
-  # With +try+
-  #   @person.try(:children).try(:first).try(:name)
-  def try(_method_name = nil, *)
-    nil
-  end
-
-  # Calling +try!+ on +nil+ always returns +nil+.
-  #
-  #   nil.try!(:name) # => nil
-  def try!(_method_name = nil, *)
-    nil
-  end
-end