diff --git a/app/controllers/concerns/documentation_controller_branding.rb b/app/controllers/concerns/documentation_controller_branding.rb
index fbfa580..d6fcf0a 100644
--- a/app/controllers/concerns/documentation_controller_branding.rb
+++ b/app/controllers/concerns/documentation_controller_branding.rb
@@ -33,8 +33,7 @@ def wiki_url(section: '')
   # We do not use flavor downstream, but keeping it here for the same method signature
   # rubocop:disable Lint/UnusedMethodArgument
   def docs_url(guide:, flavor:, chapter: nil)
-    url = ForemanThemeSatellite::Documentation::DOCS_GUIDES_LINKS.dig(guide, chapter)
-    url || "#{ForemanThemeSatellite.documentation_root}/#{guide.downcase}/#{chapter}"
+    ForemanThemeSatellite::Documentation.docs_url(guide, chapter, logger: Foreman::Logging.logger('app'))
   end
   # rubocop:enable Lint/UnusedMethodArgument
 end
diff --git a/test/fixtures/toc.json b/lib/foreman_theme_satellite/documentation-toc.json
similarity index 100%
rename from test/fixtures/toc.json
rename to lib/foreman_theme_satellite/documentation-toc.json
diff --git a/lib/foreman_theme_satellite/documentation.rb b/lib/foreman_theme_satellite/documentation.rb
index dfb8171..d1f133b 100644
--- a/lib/foreman_theme_satellite/documentation.rb
+++ b/lib/foreman_theme_satellite/documentation.rb
@@ -73,32 +73,59 @@ module Documentation
       'foreman_discovery' => "#{ForemanThemeSatellite.documentation_root}/provisioning_hosts/discovering-hosts-on-a-network_provisioning",
     }.freeze
 
-    DOCS_GUIDES_LINKS = {
-      'Managing_Content' => {
-        'Products_and_Repositories_content-management' => "#{ForemanThemeSatellite.documentation_root}/managing_content/importing_content_content-management#Products_and_Repositories_content-management",
-      },
+    # Guide mapping. If no entry is present, it should be assumed that it can
+    # be downcased
+    # Copied from foreman-documentation's upstream_filename_to_satellite_link.json
+    DOCS_GUIDE_MAPPING = {
+      'Administering_Project' => 'administering_red_hat_satellite',
+      'Configuring_Load_Balancer' => 'configuring_capsules_with_a_load_balancer',
+      'Deploying_Project_on_AWS' => 'deploying_red_hat_satellite_on_amazon_web_services',
+      'Installing_Proxy' => 'installing_capsule_server',
+      'Installing_Server' => 'installing_satellite_server_in_a_connected_network_environment',
+      'Installing_Server_Disconnected' => 'installing_satellite_server_in_a_disconnected_network_environment',
+      'Managing_Configurations_Ansible' => 'managing_configurations_using_ansible_integration',
+      'Managing_Configurations_Puppet' => 'managing_configurations_using_puppet_integration',
+      'Managing_Content' => 'managing_content',
+      'Managing_Hosts' => 'managing_hosts',
+      'Managing_Security_Compliance' => 'managing_security_compliance',
+      'Monitoring_Project' => 'monitoring_satellite_performance',
+      'Planning_for_Project' => 'overview_concepts_and_deployment_considerations',
+      'Provisioning_Hosts' => 'provisioning_hosts',
+      'Tuning_Performance' => 'tuning_performance_of_red_hat_satellite',
+      'Updating_Project' => 'updating_red_hat_satellite',
+      'Upgrading_Project' => "upgrading_connected_red_hat_satellite_to_#{SATELLITE_SHORT_VERSION}",
+      'Upgrading_Project_Disconnected' => "upgrading_disconnected_red_hat_satellite_to_#{SATELLITE_SHORT_VERSION}",
+    }.freeze
+
+    # An upstream chapter mapping, in case downstream another chapter should be
+    # used. The top level key is the upstream guide name where the value is a
+    # mapping of upstream chapter to downstream mapping
+    DOCS_GUIDE_CHAPTER_MAPPING = {
       'Managing_Hosts' => {
-        'registering-a-host_managing-hosts' => "#{ForemanThemeSatellite.documentation_root}/managing_hosts/registering_hosts_to_server_managing-hosts#Registering_Hosts_by_Using_Global_Registration_managing-hosts",
+        'registering-a-host_managing-hosts' => 'Registering_Hosts_by_Using_Global_Registration_managing-hosts',
       },
-      'Managing_Configurations_Ansible' => {
-        'Importing_Ansible_Roles_and_Variables_ansible' => "#{ForemanThemeSatellite.documentation_root}/managing_configurations_using_ansible_integration/getting_started_with_ansible_in_satellite_ansible#Importing_Ansible_Roles_and_Variables_ansible",
-        'Overriding_Ansible_Variables_in_foreman_ansible' => "#{ForemanThemeSatellite.documentation_root}/managing_configurations_using_ansible_integration/getting_started_with_ansible_in_satellite_ansible#Overriding_Ansible_Variables_in_satellite_ansible",
-      }
     }.freeze
 
-    def self.flat_docs_guides_links
-      nested_to_flat_k_v(nil, DOCS_GUIDES_LINKS).to_h
-    end
+    DOCS_GUIDE_PAGES = JSON.load_file(File.join(__dir__, 'documentation-toc.json'))
+
+    def self.docs_url(guide, chapter, logger:)
+      root = ForemanThemeSatellite.documentation_root
+      downstream_guide = DOCS_GUIDE_MAPPING.fetch(guide) do
+        logger.debug("Could not find downstream guide for '#{guide}'")
+        guide.downcase
+      end
+
+      if chapter
+        downstream_chapter = DOCS_GUIDE_CHAPTER_MAPPING.fetch(guide, chapter) || chapter
 
-    private_class_method def self.nested_to_flat_k_v(prefix, source)
-      key_values = []
-      source.map do |k, v|
-        key = "#{prefix}/#{k}"
-        if v.is_a?(Hash)
-          key_values.concat(nested_to_flat_k_v(key, v))
+        if (page = DOCS_GUIDE_PAGES[downstream_guide]&.find { |_page, chapters| chapters.include?(downstream_chapter) }&.first)
+          "#{root}/#{downstream_guide}/#{page}##{downstream_chapter}"
         else
-          key_values.concat([[key, v]])
+          logger.warn("Could not find page for chapter '#{downstream_chapter}' in guide '#{downstream_guide}'")
+          "#{root}-single/#{downstream_guide}/index##{downstream_chapter}"
         end
+      else
+        "#{root}/#{downstream_guide}"
       end
       key_values
     end
diff --git a/lib/tasks/foreman_theme_satellite_tasks.rake b/lib/tasks/foreman_theme_satellite_tasks.rake
index eed2acf..a0ea41e 100644
--- a/lib/tasks/foreman_theme_satellite_tasks.rake
+++ b/lib/tasks/foreman_theme_satellite_tasks.rake
@@ -18,7 +18,7 @@ namespace :foreman_theme_satellite do
   task :validate_docs do
     toc_file = ENV['TOC']
     unless toc_file
-      toc_file = File.expand_path('../../test/fixtures/toc.json', __dir__)
+      toc_file = File.expand_path('../foreman_theme_satellite/documentation-toc.json', __dir__)
       puts "Using default TOC: #{toc_file}, to override please specify TOC=<toc_file>"
     end
 
@@ -29,13 +29,12 @@ namespace :foreman_theme_satellite do
 
     all_links = ForemanThemeSatellite::Documentation::USER_GUIDE_DICTIONARY
                 .merge(ForemanThemeSatellite::Documentation::PLUGINS_DOCUMENTATION)
-                .merge(ForemanThemeSatellite::Documentation.flat_docs_guides_links)
 
     failed = all_links.filter { |_key, doc_address| doc_address.include?('/html/') && !checker.test_link(doc_address) }
 
     abort((failed.map { |key, doc_address| "FAILED: Cannot find #{doc_address} in TOC for entry: #{key}" } + ["Total failed: #{failed.count} entries"]).join("\n")) unless failed.empty?
 
-    puts "Successfully tested #{all_links.count} links"
+    puts "Successfully tested #{all_links.count + docs_guide_mapping.each_value.sum(&:length)} links"
   end
 end
 
diff --git a/test/integration/documentation_controller_branding_test.rb b/test/integration/documentation_controller_branding_test.rb
index 42df429..83e165b 100644
--- a/test/integration/documentation_controller_branding_test.rb
+++ b/test/integration/documentation_controller_branding_test.rb
@@ -7,9 +7,55 @@ def test_docs_redirect_branded
     assert_redirected_to "https://docs.redhat.com/documentation/en-us/red_hat_satellite/#{ForemanThemeSatellite.documentation_version}/html/managing_hosts/registering_hosts_to_server_managing-hosts#Registering_Hosts_by_Using_Global_Registration_managing-hosts"
   end
 
+  def test_docs_dynamically_generated
+    get "/links/docs/Managing_Content?chapter=Products_and_Repositories_content-management"
+
+    assert_redirected_to "https://docs.redhat.com/documentation/en-us/red_hat_satellite/#{ForemanThemeSatellite.documentation_version}/html/managing_content/importing_content_content-management#Products_and_Repositories_content-management"
+  end
+
+  def test_docs_with_mapped_guide
+    get "/links/docs/Managing_Configurations_Ansible?chapter=Importing_Ansible_Roles_and_Variables_ansible"
+
+    assert_redirected_to "https://docs.redhat.com/documentation/en-us/red_hat_satellite/#{ForemanThemeSatellite.documentation_version}/html/managing_configurations_using_ansible/getting_started_with_ansible_in_satellite_ansible_integration#Importing_Ansible_Roles_and_Variables_ansible"
+  end
+
+  def test_docs_chapter_does_not_exist
+    get "/links/docs/Managing_Content?chapter=does-not-exist"
+
+    assert_redirected_to "https://docs.redhat.com/documentation/en-us/red_hat_satellite/#{ForemanThemeSatellite.documentation_version}/html-single/managing_content/index#does-not-exist"
+  end
+
   def test_docs_redirect_unknown_chapter
     get "/links/docs/Managing_Hosts"
 
     assert_redirected_to "https://docs.redhat.com/documentation/en-us/red_hat_satellite/#{ForemanThemeSatellite.documentation_version}/html/managing_hosts/"
   end
+
+  def test_docs_guide_chapter_mapping
+    logger = mock
+
+    ForemanThemeSatellite::Documentation::DOCS_GUIDE_CHAPTER_MAPPING.each do |guide, chapters|
+      chapters.each_key do |chapter|
+        url = ForemanThemeSatellite::Documentation.docs_url(guide, chapter, logger: logger)
+        assert_not_includes(url, 'html-single')
+      end
+    end
+  end
+
+  def test_many
+    {
+      'Managing_Content' => {
+        'Products_and_Repositories_content-management' => "#{ForemanThemeSatellite.documentation_root}/managing_content/importing_content_content-management#Products_and_Repositories_content-management",
+      },
+      'Managing_Configurations_Ansible' => {
+        'Importing_Ansible_Roles_and_Variables_ansible' => "#{ForemanThemeSatellite.documentation_root}/managing_configurations_using_ansible_integration/getting_started_with_ansible_in_satellite_ansible#Importing_Ansible_Roles_and_Variables_ansible",
+        'Overriding_Ansible_Variables_in_foreman_ansible' => "#{ForemanThemeSatellite.documentation_root}/managing_configurations_using_ansible_integration/getting_started_with_ansible_in_satellite_ansible#Overriding_Ansible_Variables_in_satellite_ansible",
+      },
+    }.each do |guide, chapters|
+      chapters.each do |chapter, expected|
+        get "/links/docs/#{guide}?chapter=#{chapter}"
+        assert_redirected_to expected
+      end
+    end
+  end
 end