diff --git a/Library/Homebrew/livecheck/strategy/pypi.rb b/Library/Homebrew/livecheck/strategy/pypi.rb
index c598b331680fac..0d1a27cac0a84d 100644
--- a/Library/Homebrew/livecheck/strategy/pypi.rb
+++ b/Library/Homebrew/livecheck/strategy/pypi.rb
@@ -1,9 +1,6 @@
 # typed: strict
 # frozen_string_literal: true
 
-require "json"
-require "utils/curl"
-
 module Homebrew
   module Livecheck
     module Strategy
@@ -21,6 +18,14 @@ module Strategy
       class Pypi
         NICE_NAME = "PyPI"
 
+        # The default `strategy` block used to extract version information when
+        # a `strategy` block isn't provided.
+        DEFAULT_BLOCK = T.let(proc do |json|
+          json.dig("info", "version")
+        end.freeze, T.proc.params(
+          arg0: T::Hash[String, T.untyped],
+        ).returns(T.nilable(String)))
+
         # The `Regexp` used to extract the package name and suffix (e.g. file
         # extension) from the URL basename.
         FILENAME_REGEX = /
@@ -47,7 +52,7 @@ def self.match?(url)
         end
 
         # Extracts the package name from the provided URL and generates the
-        # PyPI JSON API endpoint.
+        # PyPI JSON API URL.
         #
         # @param url [String] the URL used to generate values
         # @return [Hash]
@@ -58,48 +63,52 @@ def self.generate_input_values(url)
           match = File.basename(url).match(FILENAME_REGEX)
           return values if match.blank?
 
-          package_name = T.must(match[:package_name]).gsub(/[_-]/, "-")
-          values[:url] = "https://pypi.org/project/#{package_name}/#files"
-          values[:regex] = %r{href=.*?/packages.*?/#{package_name}[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)\.t}i
+          values[:url] = "https://pypi.org/pypi/#{T.must(match[:package_name]).gsub(/%20|_/, "-")}/json"
 
           values
         end
 
-        # Fetches the latest version of the package from the PyPI JSON API.
+        # Generates a URL, fetches the JSON content, and identifies new
+        # versions using {Json#versions_from_content} with a block.
         #
         # @param url [String] the URL of the content to check
-        # @param regex [Regexp] a regex used for matching versions in content (optional)
+        # @param regex [Regexp] a regex used for matching versions in content
+        # @param provided_content [String, nil] content to check instead of
+        #   fetching
+        # @param homebrew_curl [Boolean] whether to use brewed curl with the URL
         # @return [Hash]
         sig {
           params(
-            url:     String,
-            regex:   T.nilable(Regexp),
-            _unused: T.untyped,
-            _block:  T.nilable(Proc),
+            url:              String,
+            regex:            T.nilable(Regexp),
+            provided_content: T.nilable(String),
+            homebrew_curl:    T::Boolean,
+            _unused:          T.untyped,
+            block:            T.nilable(Proc),
           ).returns(T::Hash[Symbol, T.untyped])
         }
-        def self.find_versions(url:, regex: nil, **_unused, &_block)
+        def self.find_versions(url:, regex: nil, provided_content: nil, homebrew_curl: false, **_unused, &block)
           match_data = { matches: {}, regex:, url: }
+          match_data[:cached] = true if provided_content.is_a?(String)
 
           generated = generate_input_values(url)
           return match_data if generated.blank?
 
           match_data[:url] = generated[:url]
 
-          # Parse JSON and get the latest version
-          begin
-            response = Utils::Curl.curl_output(generated[:url])
-            data = JSON.parse(response.stdout, symbolize_names: true)
-            latest_version = data.dig(:info, :version)
-          rescue => e
-            puts "Error fetching version from PyPI: #{e.message}"
-            return {}
+          content = if provided_content
+            provided_content
+          else
+            match_data.merge!(Strategy.page_content(match_data[:url], homebrew_curl:))
+            match_data[:content]
           end
+          return match_data unless content
 
-          # Return the version if found
-          return {} if latest_version.blank?
+          Json.versions_from_content(content, regex, &block || DEFAULT_BLOCK).each do |match_text|
+            match_data[:matches][match_text] = Version.new(match_text)
+          end
 
-          { matches: { latest_version => Version.new(latest_version) } }
+          match_data
         end
       end
     end
diff --git a/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb b/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb
index f42a3d174c5807..2ee5aa35e8786d 100644
--- a/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb
+++ b/Library/Homebrew/test/livecheck/strategy/pypi_spec.rb
@@ -10,8 +10,7 @@
 
   let(:generated) do
     {
-      url:   "https://pypi.org/project/example-package/#files",
-      regex: %r{href=.*?/packages.*?/example-package[._-]v?(\d+(?:\.\d+)*(?:[._-]post\d+)?)\.t}i,
+      url: "https://pypi.org/pypi/example-package/json",
     }
   end