diff --git a/Library/Homebrew/bundle_version.rb b/Library/Homebrew/bundle_version.rb
index 16854fc40d..8bf70d76ea 100644
--- a/Library/Homebrew/bundle_version.rb
+++ b/Library/Homebrew/bundle_version.rb
@@ -17,7 +17,11 @@ module Homebrew
     sig { params(info_plist_path: Pathname).returns(T.nilable(T.attached_class)) }
     def self.from_info_plist(info_plist_path)
       plist = system_command!("plutil", args: ["-convert", "xml1", "-o", "-", info_plist_path]).plist
+      from_info_plist_content(plist)
+    end
 
+    sig { params(plist: T::Hash[String, T.untyped]).returns(T.nilable(T.attached_class)) }
+    def self.from_info_plist_content(plist)
       short_version = plist["CFBundleShortVersionString"].presence
       version = plist["CFBundleVersion"].presence
 
diff --git a/Library/Homebrew/livecheck/livecheck.rb b/Library/Homebrew/livecheck/livecheck.rb
index 92097bb711..cdb85e265c 100644
--- a/Library/Homebrew/livecheck/livecheck.rb
+++ b/Library/Homebrew/livecheck/livecheck.rb
@@ -501,8 +501,7 @@ module Homebrew
           regex_provided:     livecheck_regex.present?,
           block_provided:     livecheck.strategy_block.present?,
         )
-        strategy = Strategy.from_symbol(livecheck_strategy)
-        strategy ||= strategies.first
+        strategy = Strategy.from_symbol(livecheck_strategy) || strategies.first
         strategy_name = livecheck_strategy_names[strategy]
 
         if debug
@@ -514,24 +513,29 @@ module Homebrew
           puts "Regex:            #{livecheck_regex.inspect}" if livecheck_regex.present?
         end
 
-        if livecheck_strategy == :page_match && (livecheck_regex.blank? && livecheck.strategy_block.blank?)
-          odebug "#{strategy_name} strategy requires a regex or block"
-          next
-        end
-
-        if livecheck_strategy.present? && livecheck_url.blank?
-          odebug "#{strategy_name} strategy requires a URL"
-          next
-        end
-
-        if livecheck_strategy.present? && strategies.exclude?(strategy)
-          odebug "#{strategy_name} strategy does not apply to this URL"
-          next
+        if livecheck_strategy.present?
+          if livecheck_strategy == :page_match && (livecheck_regex.blank? && livecheck.strategy_block.blank?)
+            odebug "#{strategy_name} strategy requires a regex or block"
+            next
+          elsif livecheck_url.blank?
+            odebug "#{strategy_name} strategy requires a URL"
+            next
+          elsif strategies.exclude?(strategy)
+            odebug "#{strategy_name} strategy does not apply to this URL"
+            next
+          end
         end
 
         next if strategy.blank?
 
-        strategy_data = strategy.find_versions(url, livecheck_regex, &livecheck.strategy_block)
+        strategy_data = begin
+          strategy.find_versions(url, livecheck_regex, cask: cask, &livecheck.strategy_block)
+        rescue ArgumentError => e
+          raise unless e.message.include?("unknown keyword: cask")
+
+          odeprecated "`def self.find_versions` in `#{strategy}` without a `cask` parameter"
+          strategy.find_versions(url, livecheck_regex, &livecheck.strategy_block)
+        end
         match_version_map = strategy_data[:matches]
         regex = strategy_data[:regex]
         messages = strategy_data[:messages]
@@ -559,7 +563,9 @@ module Homebrew
           end
         end
 
-        if debug && match_version_map.present?
+        next if match_version_map.blank?
+
+        if debug
           puts
           puts "Matched Versions:"
 
@@ -572,8 +578,6 @@ module Homebrew
           end
         end
 
-        next if match_version_map.blank?
-
         version_info = {
           latest: Version.new(match_version_map.values.max_by { |v| LivecheckVersion.create(formula_or_cask, v) }),
         }
diff --git a/Library/Homebrew/livecheck/strategy.rb b/Library/Homebrew/livecheck/strategy.rb
index 69a139e161..76b1edfd79 100644
--- a/Library/Homebrew/livecheck/strategy.rb
+++ b/Library/Homebrew/livecheck/strategy.rb
@@ -148,6 +148,7 @@ require_relative "strategy/apache"
 require_relative "strategy/bitbucket"
 require_relative "strategy/cpan"
 require_relative "strategy/electron_builder"
+require_relative "strategy/extract_plist"
 require_relative "strategy/git"
 require_relative "strategy/github_latest"
 require_relative "strategy/gnome"
diff --git a/Library/Homebrew/livecheck/strategy/apache.rb b/Library/Homebrew/livecheck/strategy/apache.rb
index c96f0b903c..2fdbbcb1fe 100644
--- a/Library/Homebrew/livecheck/strategy/apache.rb
+++ b/Library/Homebrew/livecheck/strategy/apache.rb
@@ -21,6 +21,8 @@ module Homebrew
       #
       # @api public
       class Apache
+        extend T::Sig
+
         # The `Regexp` used to determine if the strategy applies to the URL.
         URL_MATCH_REGEX = %r{
           ^https?://www\.apache\.org
@@ -45,7 +47,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           # Use `\.t` instead of specific tarball extensions (e.g. .tar.gz)
@@ -60,7 +70,7 @@ module Homebrew
           # * `/href=["']?example-v?(\d+(?:\.\d+)+)-bin\.zip/i`
           regex ||= /href=["']?#{Regexp.escape(match[:prefix])}v?(\d+(?:\.\d+)+)#{Regexp.escape(suffix)}/i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/bitbucket.rb b/Library/Homebrew/livecheck/strategy/bitbucket.rb
index dfa3539836..754d2c5e37 100644
--- a/Library/Homebrew/livecheck/strategy/bitbucket.rb
+++ b/Library/Homebrew/livecheck/strategy/bitbucket.rb
@@ -28,6 +28,8 @@ module Homebrew
       #
       # @api public
       class Bitbucket
+        extend T::Sig
+
         # The `Regexp` used to determine if the strategy applies to the URL.
         URL_MATCH_REGEX = %r{
           ^https?://bitbucket\.org
@@ -52,7 +54,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           # Use `\.t` instead of specific tarball extensions (e.g. .tar.gz)
@@ -71,7 +81,7 @@ module Homebrew
           # * `/href=.*?example-v?(\d+(?:\.\d+)+)\.t/i`
           regex ||= /href=.*?#{Regexp.escape(match[:prefix])}v?(\d+(?:\.\d+)+)#{Regexp.escape(suffix)}/i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/cpan.rb b/Library/Homebrew/livecheck/strategy/cpan.rb
index 235254254c..f642f200a0 100644
--- a/Library/Homebrew/livecheck/strategy/cpan.rb
+++ b/Library/Homebrew/livecheck/strategy/cpan.rb
@@ -18,6 +18,8 @@ module Homebrew
       #
       # @api public
       class Cpan
+        extend T::Sig
+
         NICE_NAME = "CPAN"
 
         # The `Regexp` used to determine if the strategy applies to the URL.
@@ -43,7 +45,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           # Use `\.t` instead of specific tarball extensions (e.g. .tar.gz)
@@ -55,7 +65,7 @@ module Homebrew
           # Example regex: `/href=.*?Brew[._-]v?(\d+(?:\.\d+)*)\.t/i`
           regex ||= /href=.*?#{match[:prefix]}[._-]v?(\d+(?:\.\d+)*)#{Regexp.escape(suffix)}/i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/electron_builder.rb b/Library/Homebrew/livecheck/strategy/electron_builder.rb
index b03fdb81a6..9c59b9114a 100644
--- a/Library/Homebrew/livecheck/strategy/electron_builder.rb
+++ b/Library/Homebrew/livecheck/strategy/electron_builder.rb
@@ -64,10 +64,11 @@ module Homebrew
           params(
             url:   String,
             regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
             block: T.nilable(T.proc.params(arg0: Hash).returns(String)),
           ).returns(T::Hash[Symbol, T.untyped])
         }
-        def self.find_versions(url, regex = nil, &block)
+        def self.find_versions(url, regex, cask: nil, &block)
           raise ArgumentError, "The #{T.must(name).demodulize} strategy does not support a regex." if regex
 
           match_data = { matches: {}, regex: regex, url: url }
diff --git a/Library/Homebrew/livecheck/strategy/extract_plist.rb b/Library/Homebrew/livecheck/strategy/extract_plist.rb
new file mode 100644
index 0000000000..7b24e3bafb
--- /dev/null
+++ b/Library/Homebrew/livecheck/strategy/extract_plist.rb
@@ -0,0 +1,91 @@
+# typed: true
+# frozen_string_literal: true
+
+require "bundle_version"
+require "unversioned_cask_checker"
+require_relative "page_match"
+
+module Homebrew
+  module Livecheck
+    module Strategy
+      # The {ExtractPlist} strategy downloads the file at a URL and
+      # extracts versions from contained `.plist` files.
+      #
+      # @api private
+      class ExtractPlist
+        extend T::Sig
+
+        # A priority of zero causes livecheck to skip the strategy. We only
+        # apply {ExtractPlist} using `strategy :extract_plist` in a `livecheck` block,
+        # as we can't automatically determine when this can be successfully
+        # applied to a URL without fetching the content.
+        PRIORITY = 0
+
+        # The `Regexp` used to determine if the strategy applies to the URL.
+        URL_MATCH_REGEX = %r{^https?://}i.freeze
+
+        # Whether the strategy can be applied to the provided URL.
+        # The strategy will technically match any HTTP URL but is
+        # only usable with a `livecheck` block containing a regex
+        # or block.
+        sig { params(url: String).returns(T::Boolean) }
+        def self.match?(url)
+          URL_MATCH_REGEX.match?(url)
+        end
+
+        # @api private
+        Item = Struct.new(
+          # @api private
+          :bundle_version,
+          keyword_init: true,
+        ) do
+          extend T::Sig
+
+          extend Forwardable
+
+          # @api public
+          delegate version: :bundle_version
+
+          # @api public
+          delegate short_version: :bundle_version
+        end
+
+        # Checks the content at the URL for new versions.
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  Cask::Cask,
+            block: T.nilable(T.proc.params(arg0: T::Hash[String, Item]).returns(String)),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask:, &block)
+          raise ArgumentError, "The #{T.must(name).demodulize} strategy does not support a regex." if regex
+          raise ArgumentError, "The #{T.must(name).demodulize} strategy only supports casks." unless T.unsafe(cask)
+
+          match_data = { matches: {}, regex: regex, url: url }
+
+          unversioned_cask_checker = UnversionedCaskChecker.new(cask)
+          versions = unversioned_cask_checker.all_versions.transform_values { |v| Item.new(bundle_version: v) }
+
+          if block
+            match = block.call(versions)
+
+            unless T.unsafe(match).is_a?(String)
+              raise TypeError, "Return value of `strategy :extract_plist` block must be a string."
+            end
+
+            match_data[:matches][match] = Version.new(match) if match
+          elsif versions.any?
+            versions.each_value do |item|
+              version = item.bundle_version.nice_version
+              match_data[:matches][version] = Version.new(version)
+            end
+          end
+
+          match_data
+        end
+      end
+    end
+  end
+end
diff --git a/Library/Homebrew/livecheck/strategy/git.rb b/Library/Homebrew/livecheck/strategy/git.rb
index f57e047666..c681d5282a 100644
--- a/Library/Homebrew/livecheck/strategy/git.rb
+++ b/Library/Homebrew/livecheck/strategy/git.rb
@@ -24,6 +24,8 @@ module Homebrew
       #
       # @api public
       class Git
+        extend T::Sig
+
         # The priority of the strategy on an informal scale of 1 to 10 (from
         # lowest to highest).
         PRIORITY = 8
@@ -74,7 +76,16 @@ module Homebrew
         # @param url [String] the URL of the Git repository to check
         # @param regex [Regexp] the regex to use for matching versions
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: T::Array[String])
+            .returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match_data = { matches: {}, regex: regex, url: url }
 
           tags_data = tag_info(url, regex)
diff --git a/Library/Homebrew/livecheck/strategy/github_latest.rb b/Library/Homebrew/livecheck/strategy/github_latest.rb
index 8197e635ad..d29888f329 100644
--- a/Library/Homebrew/livecheck/strategy/github_latest.rb
+++ b/Library/Homebrew/livecheck/strategy/github_latest.rb
@@ -32,6 +32,8 @@ module Homebrew
       #
       # @api public
       class GithubLatest
+        extend T::Sig
+
         NICE_NAME = "GitHub - Latest"
 
         # A priority of zero causes livecheck to skip the strategy. We do this
@@ -60,7 +62,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.sub(/\.git$/i, "").match(URL_MATCH_REGEX)
 
           # Example URL: `https://github.com/example/example/releases/latest`
@@ -69,7 +79,7 @@ module Homebrew
           # The default regex is the same for all URLs using this strategy
           regex ||= %r{href=.*?/tag/v?(\d+(?:\.\d+)+)["' >]}i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/gnome.rb b/Library/Homebrew/livecheck/strategy/gnome.rb
index 19ea4ed70c..3eb6442cf9 100644
--- a/Library/Homebrew/livecheck/strategy/gnome.rb
+++ b/Library/Homebrew/livecheck/strategy/gnome.rb
@@ -17,6 +17,8 @@ module Homebrew
       #
       # @api public
       class Gnome
+        extend T::Sig
+
         NICE_NAME = "GNOME"
 
         # The `Regexp` used to determine if the strategy applies to the URL.
@@ -40,7 +42,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           page_url = "https://download.gnome.org/sources/#{match[:package_name]}/cache.json"
@@ -57,7 +67,7 @@ module Homebrew
           # Example regex: `/example-(\d+\.([0-8]\d*?)?[02468](?:\.\d+)*?)\.t/i`
           regex ||= /#{Regexp.escape(match[:package_name])}-(\d+\.([0-8]\d*?)?[02468](?:\.\d+)*?)\.t/i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/gnu.rb b/Library/Homebrew/livecheck/strategy/gnu.rb
index 8f2a5bcdca..a00e41ea9e 100644
--- a/Library/Homebrew/livecheck/strategy/gnu.rb
+++ b/Library/Homebrew/livecheck/strategy/gnu.rb
@@ -29,6 +29,8 @@ module Homebrew
       #
       # @api public
       class Gnu
+        extend T::Sig
+
         NICE_NAME = "GNU"
 
         # The `Regexp` used to determine if the strategy applies to the URL.
@@ -52,7 +54,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           # The directory listing page for the project's files
@@ -68,7 +78,7 @@ module Homebrew
           # Example regex: `%r{href=.*?example[._-]v?(\d+(?:\.\d+)*)(?:\.[a-z]+|/)}i`
           regex ||= %r{href=.*?#{match[:project_name]}[._-]v?(\d+(?:\.\d+)*)(?:\.[a-z]+|/)}i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/hackage.rb b/Library/Homebrew/livecheck/strategy/hackage.rb
index cb986e34ba..a780c848a8 100644
--- a/Library/Homebrew/livecheck/strategy/hackage.rb
+++ b/Library/Homebrew/livecheck/strategy/hackage.rb
@@ -17,6 +17,8 @@ module Homebrew
       #
       # @api public
       class Hackage
+        extend T::Sig
+
         # A `Regexp` used in determining if the strategy applies to the URL and
         # also as part of extracting the package name from the URL basename.
         PACKAGE_NAME_REGEX = /(?<package_name>.+?)-\d+/i.freeze
@@ -45,7 +47,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = File.basename(url).match(FILENAME_REGEX)
 
           # A page containing a directory listing of the latest source tarball
@@ -54,7 +64,7 @@ module Homebrew
           # Example regex: `%r{<h3>example-(.*?)/?</h3>}i`
           regex ||= %r{<h3>#{Regexp.escape(match[:package_name])}-(.*?)/?</h3>}i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/header_match.rb b/Library/Homebrew/livecheck/strategy/header_match.rb
index b413d0a1ba..1e10286d6a 100644
--- a/Library/Homebrew/livecheck/strategy/header_match.rb
+++ b/Library/Homebrew/livecheck/strategy/header_match.rb
@@ -35,8 +35,16 @@ module Homebrew
 
         # Checks the final URL for new versions after following all redirections,
         # using the provided regex for matching.
-        sig { params(url: String, regex: T.nilable(Regexp)).returns(T::Hash[Symbol, T.untyped]) }
-        def self.find_versions(url, regex, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: T::Hash[String, String])
+            .returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match_data = { matches: {}, regex: regex, url: url }
 
           headers = Strategy.page_headers(url)
@@ -45,7 +53,7 @@ module Homebrew
           merged_headers = headers.reduce(&:merge)
 
           if block
-            match = block.call(merged_headers, regex)
+            match = yield merged_headers, regex
           else
             match = nil
 
diff --git a/Library/Homebrew/livecheck/strategy/launchpad.rb b/Library/Homebrew/livecheck/strategy/launchpad.rb
index a871973b03..1257383a3e 100644
--- a/Library/Homebrew/livecheck/strategy/launchpad.rb
+++ b/Library/Homebrew/livecheck/strategy/launchpad.rb
@@ -23,6 +23,8 @@ module Homebrew
       #
       # @api public
       class Launchpad
+        extend T::Sig
+
         # The `Regexp` used to determine if the strategy applies to the URL.
         URL_MATCH_REGEX = %r{
           ^https?://(?:[^/]+?\.)*launchpad\.net
@@ -43,7 +45,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           # The main page for the project on Launchpad
@@ -52,7 +62,7 @@ module Homebrew
           # The default regex is the same for all URLs using this strategy
           regex ||= %r{class="[^"]*version[^"]*"[^>]*>\s*Latest version is (.+)\s*</}
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/npm.rb b/Library/Homebrew/livecheck/strategy/npm.rb
index 00abab9126..f5610f507a 100644
--- a/Library/Homebrew/livecheck/strategy/npm.rb
+++ b/Library/Homebrew/livecheck/strategy/npm.rb
@@ -17,6 +17,8 @@ module Homebrew
       #
       # @api public
       class Npm
+        extend T::Sig
+
         NICE_NAME = "npm"
 
         # The `Regexp` used to determine if the strategy applies to the URL.
@@ -39,7 +41,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           page_url = "https://www.npmjs.com/package/#{match[:package_name]}?activeTab=versions"
@@ -49,7 +59,7 @@ module Homebrew
           # * `%r{href=.*?/package/@example/example/v/(\d+(?:\.\d+)+)"}i`
           regex ||= %r{href=.*?/package/#{Regexp.escape(match[:package_name])}/v/(\d+(?:\.\d+)+)"}i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/page_match.rb b/Library/Homebrew/livecheck/strategy/page_match.rb
index 689c810c1d..322fe997bc 100644
--- a/Library/Homebrew/livecheck/strategy/page_match.rb
+++ b/Library/Homebrew/livecheck/strategy/page_match.rb
@@ -81,11 +81,12 @@ module Homebrew
           params(
             url:              String,
             regex:            T.nilable(Regexp),
+            cask:             T.nilable(Cask::Cask),
             provided_content: T.nilable(String),
             block:            T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
           ).returns(T::Hash[Symbol, T.untyped])
         }
-        def self.find_versions(url, regex, provided_content = nil, &block)
+        def self.find_versions(url, regex, cask: nil, provided_content: nil, &block)
           match_data = { matches: {}, regex: regex, url: url }
 
           content = if provided_content.is_a?(String)
diff --git a/Library/Homebrew/livecheck/strategy/pypi.rb b/Library/Homebrew/livecheck/strategy/pypi.rb
index 45a07374c5..f70a28469c 100644
--- a/Library/Homebrew/livecheck/strategy/pypi.rb
+++ b/Library/Homebrew/livecheck/strategy/pypi.rb
@@ -17,6 +17,8 @@ module Homebrew
       #
       # @api public
       class Pypi
+        extend T::Sig
+
         NICE_NAME = "PyPI"
 
         # The `Regexp` used to extract the package name and suffix (e.g., file
@@ -49,7 +51,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = File.basename(url).match(FILENAME_REGEX)
 
           # Use `\.t` instead of specific tarball extensions (e.g. .tar.gz)
@@ -64,7 +74,7 @@ module Homebrew
           re_suffix = Regexp.escape(suffix)
           regex ||= %r{href=.*?/packages.*?/#{re_package_name}[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)#{re_suffix}}i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/sourceforge.rb b/Library/Homebrew/livecheck/strategy/sourceforge.rb
index 641eed700e..1175a9d700 100644
--- a/Library/Homebrew/livecheck/strategy/sourceforge.rb
+++ b/Library/Homebrew/livecheck/strategy/sourceforge.rb
@@ -31,6 +31,8 @@ module Homebrew
       #
       # @api public
       class Sourceforge
+        extend T::Sig
+
         NICE_NAME = "SourceForge"
 
         # The `Regexp` used to determine if the strategy applies to the URL.
@@ -55,7 +57,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           match = url.match(URL_MATCH_REGEX)
 
           page_url = "https://sourceforge.net/projects/#{match[:project_name]}/rss"
@@ -65,7 +75,7 @@ module Homebrew
           # create something that works for most URLs.
           regex ||= %r{url=.*?/#{Regexp.escape(match[:project_name])}/files/.*?[-_/](\d+(?:[-.]\d+)+)[-_/%.]}i
 
-          PageMatch.find_versions(page_url, regex, &block)
+          PageMatch.find_versions(page_url, regex, cask: cask, &block)
         end
       end
     end
diff --git a/Library/Homebrew/livecheck/strategy/sparkle.rb b/Library/Homebrew/livecheck/strategy/sparkle.rb
index eaa3660637..e2833eabc2 100644
--- a/Library/Homebrew/livecheck/strategy/sparkle.rb
+++ b/Library/Homebrew/livecheck/strategy/sparkle.rb
@@ -32,12 +32,24 @@ module Homebrew
           URL_MATCH_REGEX.match?(url)
         end
 
-        Item = Struct.new(:title, :url, :bundle_version, :short_version, :version, keyword_init: true) do
+        # @api private
+        Item = Struct.new(
+          # @api public
+          :title,
+          # @api public
+          :url,
+          # @api private
+          :bundle_version,
+          keyword_init: true,
+        ) do
           extend T::Sig
 
           extend Forwardable
 
+          # @api public
           delegate version: :bundle_version
+
+          # @api public
           delegate short_version: :bundle_version
         end
 
@@ -74,8 +86,6 @@ module Homebrew
               title:          title,
               url:            url,
               bundle_version: bundle_version,
-              short_version:  bundle_version&.short_version,
-              version:        bundle_version&.version,
             }.compact
 
             Item.new(**data) unless data.empty?
@@ -85,8 +95,15 @@ module Homebrew
         end
 
         # Checks the content at the URL for new versions.
-        sig { params(url: String, regex: T.nilable(Regexp)).returns(T::Hash[Symbol, T.untyped]) }
-        def self.find_versions(url, regex, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: Item).returns(String)),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           raise ArgumentError, "The #{T.must(name).demodulize} strategy does not support a regex." if regex
 
           match_data = { matches: {}, regex: regex, url: url }
@@ -96,7 +113,13 @@ module Homebrew
 
           if (item = item_from_content(content))
             match = if block
-              block.call(item)&.to_s
+              value = block.call(item)
+
+              unless T.unsafe(value).is_a?(String)
+                raise TypeError, "Return value of `strategy :sparkle` block must be a string."
+              end
+
+              value
             else
               item.bundle_version&.nice_version
             end
diff --git a/Library/Homebrew/livecheck/strategy/xorg.rb b/Library/Homebrew/livecheck/strategy/xorg.rb
index 79dddc0b23..7a05b185d4 100644
--- a/Library/Homebrew/livecheck/strategy/xorg.rb
+++ b/Library/Homebrew/livecheck/strategy/xorg.rb
@@ -38,6 +38,8 @@ module Homebrew
       #
       # @api public
       class Xorg
+        extend T::Sig
+
         NICE_NAME = "X.Org"
 
         # A `Regexp` used in determining if the strategy applies to the URL and
@@ -78,7 +80,15 @@ module Homebrew
         # @param url [String] the URL of the content to check
         # @param regex [Regexp] a regex used for matching versions in content
         # @return [Hash]
-        def self.find_versions(url, regex = nil, &block)
+        sig {
+          params(
+            url:   String,
+            regex: T.nilable(Regexp),
+            cask:  T.nilable(Cask::Cask),
+            block: T.nilable(T.proc.params(arg0: String).returns(T.any(T::Array[String], String))),
+          ).returns(T::Hash[Symbol, T.untyped])
+        }
+        def self.find_versions(url, regex, cask: nil, &block)
           file_name = File.basename(url)
           match = file_name.match(FILENAME_REGEX)
 
@@ -92,7 +102,7 @@ module Homebrew
 
           # Use the cached page content to avoid duplicate fetches
           cached_content = @page_data[page_url]
-          match_data = PageMatch.find_versions(page_url, regex, cached_content, &block)
+          match_data = PageMatch.find_versions(page_url, regex, provided_content: cached_content, cask: cask, &block)
 
           # Cache any new page content
           @page_data[page_url] = match_data[:content] if match_data[:content].present?
diff --git a/Library/Homebrew/test/livecheck/strategy/page_match_spec.rb b/Library/Homebrew/test/livecheck/strategy/page_match_spec.rb
index 62142abe18..b0ff28eab9 100644
--- a/Library/Homebrew/test/livecheck/strategy/page_match_spec.rb
+++ b/Library/Homebrew/test/livecheck/strategy/page_match_spec.rb
@@ -79,7 +79,8 @@ describe Homebrew::Livecheck::Strategy::PageMatch do
 
   describe "::find_versions?" do
     it "finds versions in provided_content" do
-      expect(page_match.find_versions(url, regex, page_content)).to eq(find_versions_cached_return_hash)
+      expect(page_match.find_versions(url, regex, provided_content: page_content))
+        .to eq(find_versions_cached_return_hash)
     end
   end
 end
diff --git a/Library/Homebrew/test/livecheck/strategy/sparkle_spec.rb b/Library/Homebrew/test/livecheck/strategy/sparkle_spec.rb
index f98e43ef00..47d7f00df5 100644
--- a/Library/Homebrew/test/livecheck/strategy/sparkle_spec.rb
+++ b/Library/Homebrew/test/livecheck/strategy/sparkle_spec.rb
@@ -10,26 +10,13 @@ describe Homebrew::Livecheck::Strategy::Sparkle do
 
   let(:appcast_data) {
     {
-      title:          "Version 1.2.3",
-      url:            "https://www.example.com/example/example.tar.gz",
-      bundle_version: Homebrew::BundleVersion.new("1.2.3", "1234"),
-      short_version:  "1.2.3",
-      version:        "1234",
+      title:         "Version 1.2.3",
+      url:           "https://www.example.com/example/example.tar.gz",
+      short_version: "1.2.3",
+      version:       "1234",
     }
   }
 
-  let(:appcast_item) {
-    Homebrew::Livecheck::Strategy::Sparkle::Item.new(
-      {
-        title:          appcast_data[:title],
-        url:            appcast_data[:url],
-        bundle_version: appcast_data[:bundle_version],
-        short_version:  appcast_data[:bundle_version]&.short_version,
-        version:        appcast_data[:bundle_version]&.version,
-      },
-    )
-  }
-
   let(:appcast_xml) {
     <<~EOS
       <?xml version="1.0" encoding="utf-8"?>
@@ -65,10 +52,10 @@ describe Homebrew::Livecheck::Strategy::Sparkle do
 
     it "returns an Item when given XML data" do
       expect(item_from_appcast_xml).to be_a(Homebrew::Livecheck::Strategy::Sparkle::Item)
-      expect(item_from_appcast_xml.title).to eq(appcast_item.title)
-      expect(item_from_appcast_xml.url).to eq(appcast_item.url)
-      expect(item_from_appcast_xml.bundle_version.short_version).to eq(appcast_item.bundle_version.short_version)
-      expect(item_from_appcast_xml.bundle_version.version).to eq(appcast_item.bundle_version.version)
+      expect(item_from_appcast_xml.title).to eq(appcast_data[:title])
+      expect(item_from_appcast_xml.url).to eq(appcast_data[:url])
+      expect(item_from_appcast_xml.short_version).to eq(appcast_data[:short_version])
+      expect(item_from_appcast_xml.version).to eq(appcast_data[:version])
     end
   end
 end
diff --git a/Library/Homebrew/unversioned_cask_checker.rb b/Library/Homebrew/unversioned_cask_checker.rb
index 1fef545e0c..01c7538f21 100644
--- a/Library/Homebrew/unversioned_cask_checker.rb
+++ b/Library/Homebrew/unversioned_cask_checker.rb
@@ -60,6 +60,56 @@ module Homebrew
       end
     end
 
+    sig { returns(T::Hash[String, BundleVersion]) }
+    def all_versions
+      versions = {}
+
+      parse_info_plist = proc do |info_plist_path|
+        plist = system_command!("plutil", args: ["-convert", "xml1", "-o", "-", info_plist_path]).plist
+
+        id = plist["CFBundleIdentifier"]
+        version = BundleVersion.from_info_plist_content(plist)
+
+        versions[id] = version if id && version
+      end
+
+      Dir.mktmpdir do |dir|
+        dir = Pathname(dir)
+
+        installer.extract_primary_container(to: dir)
+
+        info_plist_paths = apps.flat_map do |app|
+          top_level_info_plists(Pathname.glob(dir/"**"/app.source.basename/"Contents"/"Info.plist")).sort
+        end
+
+        info_plist_paths.each(&parse_info_plist)
+
+        pkg_paths = pkgs.flat_map do |pkg|
+          Pathname.glob(dir/"**"/pkg.path.basename).sort
+        end
+
+        pkg_paths.each do |pkg_path|
+          Dir.mktmpdir do |extract_dir|
+            extract_dir = Pathname(extract_dir)
+            FileUtils.rmdir extract_dir
+
+            system_command! "pkgutil", args: ["--expand-full", pkg_path, extract_dir]
+
+            top_level_info_plist_paths = top_level_info_plists(Pathname.glob(extract_dir/"**/Contents/Info.plist"))
+
+            top_level_info_plist_paths.each(&parse_info_plist)
+          ensure
+            Cask::Utils.gain_permissions_remove(extract_dir)
+            extract_dir.mkpath
+          end
+        end
+
+        nil
+      end
+
+      versions
+    end
+
     sig { returns(T.nilable(String)) }
     def guess_cask_version
       if apps.empty? && pkgs.empty?