diff --git a/lib/tasks/gitlab/tw/codeowners.rake b/lib/tasks/gitlab/tw/codeowners.rake
index 8d9aa4b03044e9fcd5c8e864ce9ed941a93b0e23..90a739e34d5f6b4d8b9b06520802316241bcdbf6 100644
--- a/lib/tasks/gitlab/tw/codeowners.rake
+++ b/lib/tasks/gitlab/tw/codeowners.rake
@@ -33,7 +33,7 @@ module TwCodeowners
     CodeOwnerRule.new('Composition Analysis', '@rdickenson'),
     CodeOwnerRule.new('Container Registry', '@z_painter'),
     CodeOwnerRule.new('Contributor Experience', '@eread'),
-    CodeOwnerRule.new('Custom Models', '@jglassman1'),
+    CodeOwnerRule.new('Custom Models', '@fneill'),
     # CodeOwnerRule.new('Database Frameworks', ''),
     # CodeOwnerRule.new('Database Operations', ''),
     # CodeOwnerRule.new('DataOps', ''),
@@ -155,6 +155,151 @@ namespace :tw do
   task :codeowners do
     require 'yaml'
 
+    CodeOwnerRule = Struct.new(:category, :writer)
+    DocumentOwnerMapping = Struct.new(:path, :writer) do
+      def writer_owns_directory?(mappings)
+        dir_mappings = mappings.select { |mapping| mapping.directory == directory }
+
+        dir_mappings.count { |mapping| mapping.writer == writer } / dir_mappings.length.to_f > 0.5
+      end
+
+      def directory
+        @directory ||= "#{File.dirname(path)}/"
+      end
+    end
+
+    # For groups without an assigned TW, comment out the line.
+    CODE_OWNER_RULES = [
+      # CodeOwnerRule.new('Activation', ''),
+      # CodeOwnerRule.new('Acquisition', ''),
+      CodeOwnerRule.new('Agent Foundations', '@sselhorn'),
+      CodeOwnerRule.new('AI Framework', '@sselhorn'),
+      # CodeOwnerRule.new('Analytics Instrumentation', ''),
+      CodeOwnerRule.new('Authentication', '@idurham'),
+      CodeOwnerRule.new('Authorization', '@idurham'),
+      CodeOwnerRule.new('Build', '@axil @eread'),
+      CodeOwnerRule.new('Cells Infrastructure', '@emily.sahlani'),
+      CodeOwnerRule.new('Code Creation', '@scawood'),
+      CodeOwnerRule.new('Code Review', '@aqualls'),
+      # CodeOwnerRule.new('Compliance', ''),
+      CodeOwnerRule.new('Composition Analysis', '@rdickenson'),
+      CodeOwnerRule.new('Container Registry', '@z_painter'),
+      CodeOwnerRule.new('Contributor Experience', '@eread'),
+      CodeOwnerRule.new('Custom Models', '@fneill'),
+      # CodeOwnerRule.new('Database Frameworks', ''),
+      # CodeOwnerRule.new('Database Operations', ''),
+      # CodeOwnerRule.new('DataOps', ''),
+      # CodeOwnerRule.new('Delivery', ''),
+      CodeOwnerRule.new('Durability', '@axil'),
+      CodeOwnerRule.new('Duo Chat', '@jglassman1'),
+      CodeOwnerRule.new('Dynamic Analysis', '@phillipwells'),
+      CodeOwnerRule.new('Editor Extensions', '@scawood'),
+      CodeOwnerRule.new('Engagement', '@kpaizee'),
+      # CodeOwnerRule.new('Environment Automation', ''),
+      # CodeOwnerRule.new('Environments', ''),
+      # CodeOwnerRule.new('Fulfillment Platform', ''),
+      CodeOwnerRule.new('Fuzz Testing', '@rdickenson'),
+      CodeOwnerRule.new('Geo', '@axil'),
+      CodeOwnerRule.new('Gitaly', '@eread'),
+      CodeOwnerRule.new('Global Search', '@ashrafkhamis'),
+      CodeOwnerRule.new('Remote Development', '@brendan777'),
+      CodeOwnerRule.new('Import', '@ashrafkhamis'),
+      CodeOwnerRule.new('Knowledge', '@msedlakjakubowski'),
+      # CodeOwnerRule.new('MLOps', ''),
+      # CodeOwnerRule.new('Mobile Devops', ''),
+      CodeOwnerRule.new('Optimize', '@lciutacu'),
+      CodeOwnerRule.new('Organizations', '@z_painter'),
+      CodeOwnerRule.new('Organization', '@lciutacu'),
+      CodeOwnerRule.new('Package Registry', '@z_painter'),
+      CodeOwnerRule.new('Pipeline Authoring', '@marcel.amirault'),
+      CodeOwnerRule.new('Pipeline Execution', '@lyspin'),
+      CodeOwnerRule.new('Pipeline Security', '@marcel.amirault'),
+      # CodeOwnerRule.new('Platform Insights', ''),
+      CodeOwnerRule.new('Product Planning', '@msedlakjakubowski'),
+      CodeOwnerRule.new('Project Management', '@msedlakjakubowski'),
+      CodeOwnerRule.new('Provision', '@lciutacu'),
+      CodeOwnerRule.new('Redirect', 'Redirect'),
+      # CodeOwnerRule.new('Respond', ''),
+      CodeOwnerRule.new('Runner', '@rsarangadharan'),
+      CodeOwnerRule.new('Hosted Runners', '@rsarangadharan'),
+      CodeOwnerRule.new('Seat Management', '@lciutacu'),
+      # CodeOwnerRule.new('Security Infrastructure', ''),
+      CodeOwnerRule.new('Security Platform Management', '@rlehmann1'),
+      CodeOwnerRule.new('Security Policies', '@rlehmann1'),
+      CodeOwnerRule.new('Secret Detection', '@phillipwells'),
+      CodeOwnerRule.new('Security Insights', '@rlehmann1'),
+      CodeOwnerRule.new('Operate', '@axil @eread'),
+      CodeOwnerRule.new('Solutions Architecture', '@jfullam @Darwinjs @sbrightwell'),
+      CodeOwnerRule.new('Source Code', '@brendan777'),
+      CodeOwnerRule.new('Static Analysis', '@rdickenson'),
+      CodeOwnerRule.new('Subscription Management', '@lciutacu'),
+      CodeOwnerRule.new('Switchboard', '@lyspin'),
+      CodeOwnerRule.new('Testing', '@eread'),
+      CodeOwnerRule.new('Tutorials', '@gl-docsteam'),
+      # CodeOwnerRule.new('US Public Sector Services', ''),
+      CodeOwnerRule.new('Utilization', '@lciutacu')
+      # CodeOwnerRule.new('Vulnerability Research', '')
+    ].freeze
+
+    CONTRIBUTOR_DOCS_PATH = '/doc/development/'
+    CONTRIBUTOR_DOCS_CODE_OWNER_RULES = [
+      CodeOwnerRule.new('AI Framework', '@gitlab-org/ai-powered'),
+      CodeOwnerRule.new('Analytics Instrumentation',
+        '@gitlab-org/analytics-section/product-analytics/engineers/frontend ' \
+        '@gitlab-org/analytics-section/analytics-instrumentation/engineers'),
+      CodeOwnerRule.new('Authentication', '@gitlab-org/software-supply-chain-security/authentication/approvers'),
+      CodeOwnerRule.new('Authorization', '@gitlab-org/software-supply-chain-security/authorization/approvers'),
+      CodeOwnerRule.new('Build', '@gitlab-org/distribution'),
+      CodeOwnerRule.new('Cells Infrastructure', '@OmarQunsulGitlab @bmarjanovic'),
+      CodeOwnerRule.new('Compliance',
+        '@gitlab-org/govern/security-policies-frontend @gitlab-org/govern/threat-insights-frontend-team ' \
+        '@gitlab-org/govern/threat-insights-backend-team'),
+      CodeOwnerRule.new('Composition Analysis',
+        '@gitlab-org/secure/composition-analysis-be @gitlab-org/secure/static-analysis'),
+      CodeOwnerRule.new('Documentation Guidelines', '@fneill @sselhorn'),
+      CodeOwnerRule.new('Duo Workflow', '@gitlab-org/ai-powered'),
+      CodeOwnerRule.new('Engineering Productivity', '@gl-dx/pipeline-maintainers'),
+      CodeOwnerRule.new('Engagement', '@gitlab-org/growth'),
+      CodeOwnerRule.new('Gitaly', '@proglottis @toon'),
+      CodeOwnerRule.new('Global Search', '@gitlab-org/search-team/migration-maintainers'),
+      CodeOwnerRule.new('Remote Development',
+        '@gitlab-org/maintainers/remote-development/backend @gitlab-org/maintainers/remote-development/frontend'),
+      CodeOwnerRule.new('Pipeline Authoring', '@gitlab-org/maintainers/cicd-verify'),
+      CodeOwnerRule.new('Pipeline Execution', '@gitlab-org/maintainers/cicd-verify'),
+      CodeOwnerRule.new('Platform Insights', '@gitlab-org/analytics-section/product-analytics/engineers/frontend'),
+      CodeOwnerRule.new('Organizations', '@abdwdd @alexpooley'),
+      CodeOwnerRule.new('Operate', '@gitlab-org/distribution'),
+      CodeOwnerRule.new('Threat Insights', '@gitlab-org/govern/threat-insights-frontend-team')
+    ].freeze
+
+    ERRORS_EXCLUDED_FILES = [
+      '/doc/architecture'
+    ].freeze
+
+    CODEOWNERS_BLOCK_BEGIN = "# Begin rake-managed-docs-block"
+    CODEOWNERS_BLOCK_END = "# End rake-managed-docs-block"
+
+    Document = Struct.new(:group, :redirect) do
+      def has_a_valid_group?
+        group && !redirect
+      end
+
+      def missing_metadata?
+        !group && !redirect
+      end
+    end
+
+    def self.writer_for_group(category, path)
+      rules = path.start_with?(CONTRIBUTOR_DOCS_PATH) ? CONTRIBUTOR_DOCS_CODE_OWNER_RULES : CODE_OWNER_RULES
+      writer = rules.find { |rule| rule.category == category }&.writer
+
+      if writer.is_a?(String) || writer.nil?
+        writer
+      else
+        writer.call(path)
+      end
+    end
+
     errors = []
     mappings = []