diff --git a/app/finders/main_theme.rb b/app/finders/main_theme.rb
index d353d451..377e8287 100644
--- a/app/finders/main_theme.rb
+++ b/app/finders/main_theme.rb
@@ -1,8 +1,10 @@
 # frozen_string_literal: true
 
-require_relative 'main_theme/css_style'
+require_relative 'main_theme/css_style_in_homepage'
+require_relative 'main_theme/css_style_in_404_page'
 require_relative 'main_theme/woo_framework_meta_generator'
 require_relative 'main_theme/urls_in_homepage'
+require_relative 'main_theme/urls_in_404_page'
 
 module WPScan
   module Finders
@@ -14,9 +16,11 @@ module WPScan
         # @param [ WPScan::Target ] target
         def initialize(target)
           finders <<
-            MainTheme::CssStyle.new(target) <<
+            MainTheme::CssStyleInHomepage.new(target) <<
+            MainTheme::CssStyleIn404Page.new(target) <<
             MainTheme::WooFrameworkMetaGenerator.new(target) <<
-            MainTheme::UrlsInHomepage.new(target)
+            MainTheme::UrlsInHomepage.new(target) <<
+            MainTheme::UrlsIn404Page.new(target)
         end
       end
     end
diff --git a/app/finders/main_theme/css_style_in_404_page.rb b/app/finders/main_theme/css_style_in_404_page.rb
new file mode 100644
index 00000000..bbba5036
--- /dev/null
+++ b/app/finders/main_theme/css_style_in_404_page.rb
@@ -0,0 +1,14 @@
+# frozen_string_literal: true
+
+module WPScan
+  module Finders
+    module MainTheme
+      # From the CSS style in the 404 page
+      class CssStyleIn404Page < CssStyleInHomepage
+        def passive(opts = {})
+          passive_from_css_href(target.error_404_res, opts) || passive_from_style_code(target.error_404_res, opts)
+        end
+      end
+    end
+  end
+end
diff --git a/app/finders/main_theme/css_style.rb b/app/finders/main_theme/css_style_in_homepage.rb
similarity index 85%
rename from app/finders/main_theme/css_style.rb
rename to app/finders/main_theme/css_style_in_homepage.rb
index 4b978311..34bb8619 100644
--- a/app/finders/main_theme/css_style.rb
+++ b/app/finders/main_theme/css_style_in_homepage.rb
@@ -3,9 +3,9 @@
 module WPScan
   module Finders
     module MainTheme
-      # From the css style
-      class CssStyle < CMSScanner::Finders::Finder
-        include Finders::WpItems::URLsInHomepage
+      # From the CSS style in the homepage
+      class CssStyleInHomepage < CMSScanner::Finders::Finder
+        include Finders::WpItems::UrlsInPage # To have the item_code_pattern method available here
 
         def create_theme(slug, style_url, opts)
           Model::Theme.new(
diff --git a/app/finders/main_theme/urls_in_404_page.rb b/app/finders/main_theme/urls_in_404_page.rb
new file mode 100644
index 00000000..55ffd407
--- /dev/null
+++ b/app/finders/main_theme/urls_in_404_page.rb
@@ -0,0 +1,15 @@
+# frozen_string_literal: true
+
+module WPScan
+  module Finders
+    module MainTheme
+      # URLs In 404 Page Finder
+      class UrlsIn404Page < UrlsInHomepage
+        # @return [ Typhoeus::Response ]
+        def page_res
+          @page_res ||= target.error_404_res
+        end
+      end
+    end
+  end
+end
diff --git a/app/finders/main_theme/urls_in_homepage.rb b/app/finders/main_theme/urls_in_homepage.rb
index b424d2ff..49c31004 100644
--- a/app/finders/main_theme/urls_in_homepage.rb
+++ b/app/finders/main_theme/urls_in_homepage.rb
@@ -5,7 +5,7 @@ module WPScan
     module MainTheme
       # URLs In Homepage Finder
       class UrlsInHomepage < CMSScanner::Finders::Finder
-        include WpItems::URLsInHomepage
+        include WpItems::UrlsInPage
 
         # @param [ Hash ] opts
         #
@@ -21,6 +21,11 @@ module WPScan
 
           found
         end
+
+        # @return [ Typhoeus::Response ]
+        def page_res
+          @page_res ||= target.homepage_res
+        end
       end
     end
   end
diff --git a/app/finders/main_theme/woo_framework_meta_generator.rb b/app/finders/main_theme/woo_framework_meta_generator.rb
index 427dc83c..03d9e68c 100644
--- a/app/finders/main_theme/woo_framework_meta_generator.rb
+++ b/app/finders/main_theme/woo_framework_meta_generator.rb
@@ -10,7 +10,7 @@ module WPScan
         PATTERN           = /#{THEME_PATTERN}\s+#{FRAMEWORK_PATTERN}/i.freeze
 
         def passive(opts = {})
-          return unless target.homepage_res.body =~ PATTERN
+          return unless target.homepage_res.body =~ PATTERN || target.error_404_res.body =~ PATTERN
 
           Model::Theme.new(
             Regexp.last_match[1],
diff --git a/app/finders/plugins.rb b/app/finders/plugins.rb
index 2efc8e74..926fd746 100644
--- a/app/finders/plugins.rb
+++ b/app/finders/plugins.rb
@@ -1,6 +1,7 @@
 # frozen_string_literal: true
 
 require_relative 'plugins/urls_in_homepage'
+require_relative 'plugins/urls_in_404_page'
 require_relative 'plugins/known_locations'
 # From the DynamicFinders
 require_relative 'plugins/comment'
@@ -22,6 +23,7 @@ module WPScan
         def initialize(target)
           finders <<
             Plugins::UrlsInHomepage.new(target) <<
+            Plugins::UrlsIn404Page.new(target) <<
             Plugins::HeaderPattern.new(target) <<
             Plugins::Comment.new(target) <<
             Plugins::Xpath.new(target) <<
diff --git a/app/finders/plugins/urls_in_404_page.rb b/app/finders/plugins/urls_in_404_page.rb
new file mode 100644
index 00000000..b5422900
--- /dev/null
+++ b/app/finders/plugins/urls_in_404_page.rb
@@ -0,0 +1,16 @@
+# frozen_string_literal: true
+
+module WPScan
+  module Finders
+    module Plugins
+      # URLs In 404 Page Finder
+      # Typically, the items detected from URLs like /wp-content/plugins/<slug>/
+      class UrlsIn404Page < UrlsInHomepage
+        # @return [ Typhoeus::Response ]
+        def page_res
+          @page_res ||= target.error_404_res
+        end
+      end
+    end
+  end
+end
diff --git a/app/finders/plugins/urls_in_homepage.rb b/app/finders/plugins/urls_in_homepage.rb
index 22334f9f..832005aa 100644
--- a/app/finders/plugins/urls_in_homepage.rb
+++ b/app/finders/plugins/urls_in_homepage.rb
@@ -4,10 +4,9 @@ module WPScan
   module Finders
     module Plugins
       # URLs In Homepage Finder
-      # Typically, the items detected from URLs like
-      # /wp-content/plugins/<slug>/
+      # Typically, the items detected from URLs like /wp-content/plugins/<slug>/
       class UrlsInHomepage < CMSScanner::Finders::Finder
-        include WpItems::URLsInHomepage
+        include WpItems::UrlsInPage
 
         # @param [ Hash ] opts
         #
@@ -21,6 +20,11 @@ module WPScan
 
           found
         end
+
+        # @return [ Typhoeus::Response ]
+        def page_res
+          @page_res ||= target.homepage_res
+        end
       end
     end
   end
diff --git a/app/finders/themes.rb b/app/finders/themes.rb
index 95cedffe..250f9dfd 100644
--- a/app/finders/themes.rb
+++ b/app/finders/themes.rb
@@ -1,12 +1,13 @@
 # frozen_string_literal: true
 
 require_relative 'themes/urls_in_homepage'
+require_relative 'themes/urls_in_404_page'
 require_relative 'themes/known_locations'
 
 module WPScan
   module Finders
     module Themes
-      # themes Finder
+      # Themes Finder
       class Base
         include CMSScanner::Finders::SameTypeFinder
 
@@ -14,6 +15,7 @@ module WPScan
         def initialize(target)
           finders <<
             Themes::UrlsInHomepage.new(target) <<
+            Themes::UrlsIn404Page.new(target) <<
             Themes::KnownLocations.new(target)
         end
       end
diff --git a/app/finders/themes/urls_in_404_page.rb b/app/finders/themes/urls_in_404_page.rb
new file mode 100644
index 00000000..fd393232
--- /dev/null
+++ b/app/finders/themes/urls_in_404_page.rb
@@ -0,0 +1,15 @@
+# frozen_string_literal: true
+
+module WPScan
+  module Finders
+    module Themes
+      # URLs In 04 Page Finder
+      class UrlsIn404Page < UrlsInHomepage
+        # @return [ Typhoeus::Response ]
+        def page_res
+          @page_res ||= target.error_404_res
+        end
+      end
+    end
+  end
+end
diff --git a/app/finders/themes/urls_in_homepage.rb b/app/finders/themes/urls_in_homepage.rb
index 4709bba0..c8071355 100644
--- a/app/finders/themes/urls_in_homepage.rb
+++ b/app/finders/themes/urls_in_homepage.rb
@@ -5,7 +5,7 @@ module WPScan
     module Themes
       # URLs In Homepage Finder
       class UrlsInHomepage < CMSScanner::Finders::Finder
-        include WpItems::URLsInHomepage
+        include WpItems::UrlsInPage
 
         # @param [ Hash ] opts
         #
@@ -19,6 +19,11 @@ module WPScan
 
           found
         end
+
+        # @return [ Typhoeus::Response ]
+        def page_res
+          @page_res ||= target.homepage_res
+        end
       end
     end
   end
diff --git a/app/finders/wp_items.rb b/app/finders/wp_items.rb
index ded84746..e9f1dd4b 100644
--- a/app/finders/wp_items.rb
+++ b/app/finders/wp_items.rb
@@ -1,3 +1,3 @@
 # frozen_string_literal: true
 
-require_relative 'wp_items/urls_in_homepage'
+require_relative 'wp_items/urls_in_page'
diff --git a/app/finders/wp_items/urls_in_homepage.rb b/app/finders/wp_items/urls_in_page.rb
similarity index 92%
rename from app/finders/wp_items/urls_in_homepage.rb
rename to app/finders/wp_items/urls_in_page.rb
index d17ffa44..200608c6 100644
--- a/app/finders/wp_items/urls_in_homepage.rb
+++ b/app/finders/wp_items/urls_in_page.rb
@@ -4,7 +4,7 @@ module WPScan
   module Finders
     module WpItems
       # URLs In Homepage Module to use in plugins & themes finders
-      module URLsInHomepage
+      module UrlsInPage
         # @param [ String ] type plugins / themes
         # @param [ Boolean ] uniq Wether or not to apply the #uniq on the results
         #
@@ -12,7 +12,7 @@ module WPScan
         def items_from_links(type, uniq = true)
           found = []
 
-          target.in_scope_uris(target.homepage_res) do |uri|
+          target.in_scope_uris(page_res) do |uri|
             next unless uri.to_s =~ item_attribute_pattern(type)
 
             slug = Regexp.last_match[1]&.strip
@@ -30,7 +30,7 @@ module WPScan
         def items_from_codes(type, uniq = true)
           found = []
 
-          target.homepage_res.html.xpath('//script[not(@src)]|//style[not(@src)]').each do |tag|
+          page_res.html.xpath('//script[not(@src)]|//style[not(@src)]').each do |tag|
             code = tag.text.to_s
             next if code.empty?
 
diff --git a/app/models/wp_item.rb b/app/models/wp_item.rb
index b43b6a59..e001946b 100644
--- a/app/models/wp_item.rb
+++ b/app/models/wp_item.rb
@@ -14,7 +14,7 @@ module WPScan
 
       attr_reader :uri, :slug, :detection_opts, :version_detection_opts, :blog, :path_from_blog, :db_data
 
-      delegate :homepage_res, :xpath_pattern_from_page, :in_scope_uris, :head_or_get_params, to: :blog
+      delegate :homepage_res, :error_404_res, :xpath_pattern_from_page, :in_scope_uris, :head_or_get_params, to: :blog
 
       # @param [ String ] slug The plugin/theme slug
       # @param [ Target ] blog The targeted blog
diff --git a/lib/wpscan/finders/dynamic_finder/finder.rb b/lib/wpscan/finders/dynamic_finder/finder.rb
index 60c42f94..b4349588 100644
--- a/lib/wpscan/finders/dynamic_finder/finder.rb
+++ b/lib/wpscan/finders/dynamic_finder/finder.rb
@@ -44,19 +44,27 @@ module WPScan
         #
         # @param [ Typhoeus::Response ] response
         # @param [ Hash ] opts
-        # @return [ Mixed ]
+        # @return [ Mixed: nil, Object, Array ]
         def find(_response, _opts = {})
           raise NoMethodError
         end
 
         # @param [ Hash ] opts
+        # @return [ Mixed ] See #find
         def passive(opts = {})
           return if self.class::PATH
 
-          find(target.homepage_res, opts)
+          homepage_result = find(target.homepage_res, opts)
+
+          if homepage_result
+            return homepage_result unless homepage_result.is_a?(Array) && homepage_result.empty?
+          end
+
+          find(target.error_404_res, opts)
         end
 
         # @param [ Hash ] opts
+        # @return [ Mixed ] See #find
         def aggressive(opts = {})
           return unless self.class::PATH
 
diff --git a/lib/wpscan/finders/dynamic_finder/wp_items/finder.rb b/lib/wpscan/finders/dynamic_finder/wp_items/finder.rb
index bd348550..ee460103 100644
--- a/lib/wpscan/finders/dynamic_finder/wp_items/finder.rb
+++ b/lib/wpscan/finders/dynamic_finder/wp_items/finder.rb
@@ -31,9 +31,11 @@ module WPScan
 
             passive_configs.each do |slug, configs|
               configs.each do |klass, config|
-                item = process_response(opts, target.homepage_res, slug, klass, config)
+                [target.homepage_res, target.error_404_res].each do |page_res|
+                  item = process_response(opts, page_res, slug, klass, config)
 
-                found << item if item.is_a?(Model::WpItem)
+                  found << item if item.is_a?(Model::WpItem)
+                end
               end
             end
 
diff --git a/lib/wpscan/target/platform/wordpress.rb b/lib/wpscan/target/platform/wordpress.rb
index a3360562..dbb41bc9 100644
--- a/lib/wpscan/target/platform/wordpress.rb
+++ b/lib/wpscan/target/platform/wordpress.rb
@@ -24,21 +24,10 @@ module WPScan
 
         # @param [ Symbol ] detection_mode
         #
-        # @return [ Boolean ]
-        # rubocop:disable Metrics/AbcSize, Metrics/PerceivedComplexity
+        # @return [ Boolean ] Whether or not the target is running WordPress
         def wordpress?(detection_mode)
-          in_scope_uris(homepage_res) do |uri|
-            return true if WORDPRESS_PATTERN.match?(uri.path) || WP_JSON_OEMBED_PATTERN.match?(uri.path)
-          end
-
-          return true if homepage_res.html.css('meta[name="generator"]').any? do |node|
-            /wordpress/i.match?(node['content'])
-          end
-
-          return true unless comments_from_page(/wordpress/i, homepage_res).empty?
-
-          return true if homepage_res.html.xpath('//script[not(@src)]').any? do |node|
-            WP_ADMIN_AJAX_PATTERN.match?(node.text)
+          [homepage_res, error_404_res].each do |page_res|
+            return true if wordpress_from_meta_comments_or_scripts?(page_res)
           end
 
           if %i[mixed aggressive].include?(detection_mode)
@@ -51,7 +40,26 @@ module WPScan
 
           false
         end
-        # rubocop:enable Metrics/AbcSize, Metrics/PerceivedComplexity
+
+        # @param [ Typhoeus::Response ] response
+        # @return [ Boolean ]
+        def wordpress_from_meta_comments_or_scripts?(response)
+          in_scope_uris(response) do |uri|
+            return true if WORDPRESS_PATTERN.match?(uri.path) || WP_JSON_OEMBED_PATTERN.match?(uri.path)
+          end
+
+          return true if response.html.css('meta[name="generator"]').any? do |node|
+            /wordpress/i.match?(node['content'])
+          end
+
+          return true unless comments_from_page(/wordpress/i, response).empty?
+
+          return true if response.html.xpath('//script[not(@src)]').any? do |node|
+            WP_ADMIN_AJAX_PATTERN.match?(node.text)
+          end
+
+          false
+        end
 
         COOKIE_PATTERNS = {
           'vjs' => /createCookie\('vjs','(?<c_value>\d+)',\d+\);/i
diff --git a/lib/wpscan/target/platform/wordpress/custom_directories.rb b/lib/wpscan/target/platform/wordpress/custom_directories.rb
index 1b21e557..3ca40412 100644
--- a/lib/wpscan/target/platform/wordpress/custom_directories.rb
+++ b/lib/wpscan/target/platform/wordpress/custom_directories.rb
@@ -19,13 +19,15 @@ module WPScan
             # scope_url_pattern is from CMSScanner::Target
             pattern = %r{#{scope_url_pattern}([\w\s\-/]+?)\\?/(?:themes|plugins|uploads|cache)\\?/}i
 
-            in_scope_uris(homepage_res, '//link/@href|//script/@src|//img/@src') do |uri|
-              return @content_dir = Regexp.last_match[1] if uri.to_s.match(pattern)
-            end
+            [homepage_res, error_404_res].each do |page_res|
+              in_scope_uris(page_res, '//link/@href|//script/@src|//img/@src') do |uri|
+                return @content_dir = Regexp.last_match[1] if uri.to_s.match(pattern)
+              end
 
-            # Checks for the pattern in raw JS code, as well as @content attributes of meta tags
-            xpath_pattern_from_page('//script[not(@src)]|//meta/@content', pattern, homepage_res) do |match|
-              return @content_dir = match[1]
+              # Checks for the pattern in raw JS code, as well as @content attributes of meta tags
+              xpath_pattern_from_page('//script[not(@src)]|//meta/@content', pattern, page_res) do |match|
+                return @content_dir = match[1]
+              end
             end
 
             return @content_dir = 'wp-content' if default_content_dir_exists?
@@ -104,8 +106,10 @@ module WPScan
           # url_pattern is from CMSScanner::Target
           pattern = %r{#{url_pattern}(.+?)/(?:xmlrpc\.php|wp\-includes/)}i
 
-          in_scope_uris(homepage_res) do |uri|
-            return @sub_dir = Regexp.last_match[1] if uri.to_s.match(pattern)
+          [homepage_res, error_404_res].each do |page_res|
+            in_scope_uris(page_res) do |uri|
+              return @sub_dir = Regexp.last_match[1] if uri.to_s.match(pattern)
+            end
           end
 
           @sub_dir = false
diff --git a/spec/app/finders/main_theme/css_style_in_404_page_spec.rb b/spec/app/finders/main_theme/css_style_in_404_page_spec.rb
new file mode 100644
index 00000000..ce778ed0
--- /dev/null
+++ b/spec/app/finders/main_theme/css_style_in_404_page_spec.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+describe WPScan::Finders::MainTheme::CssStyleIn404Page do
+  subject(:finder) { described_class.new(target) }
+  let(:target)     { WPScan::Target.new(url).extend(CMSScanner::Target::Server::Apache) }
+  let(:url)        { 'http://wp.lab/' }
+  let(:fixtures)   { FINDERS_FIXTURES.join('main_theme', 'css_style_in_404_page') }
+
+  # This stuff is just a child class of CssStyleInHomepage (using the error_404_res rather than homepage_res)
+  # which already has a spec
+end
diff --git a/spec/app/finders/main_theme/css_style_spec.rb b/spec/app/finders/main_theme/css_style_in_homepage_spec.rb
similarity index 87%
rename from spec/app/finders/main_theme/css_style_spec.rb
rename to spec/app/finders/main_theme/css_style_in_homepage_spec.rb
index 1cf30fb8..c067bb30 100644
--- a/spec/app/finders/main_theme/css_style_spec.rb
+++ b/spec/app/finders/main_theme/css_style_in_homepage_spec.rb
@@ -1,10 +1,10 @@
 # frozen_string_literal: true
 
-describe WPScan::Finders::MainTheme::CssStyle do
+describe WPScan::Finders::MainTheme::CssStyleInHomepage do
   subject(:finder) { described_class.new(target) }
   let(:target)     { WPScan::Target.new(url).extend(CMSScanner::Target::Server::Apache) }
   let(:url)        { 'http://wp.lab/' }
-  let(:fixtures)   { FINDERS_FIXTURES.join('main_theme', 'css_style') }
+  let(:fixtures)   { FINDERS_FIXTURES.join('main_theme', 'css_style_in_homepage') }
 
   describe '#passive' do
     after do
@@ -33,7 +33,7 @@ describe WPScan::Finders::MainTheme::CssStyle do
           @expected = WPScan::Model::Theme.new(
             'twentyfifteen',
             target,
-            found_by: 'Css Style (Passive Detection)',
+            found_by: 'Css Style In Homepage (Passive Detection)',
             confidence: 70,
             style_url: 'http://wp.lab/wp-content/themes/twentyfifteen/style.css?ver=4.1.1'
           )
@@ -47,7 +47,7 @@ describe WPScan::Finders::MainTheme::CssStyle do
           @expected = WPScan::Model::Theme.new(
             'custom',
             target,
-            found_by: 'Css Style (Passive Detection)',
+            found_by: 'Css Style In Homepage (Passive Detection)',
             confidence: 70,
             style_url: 'http://wp.lab/wp-content/themes/custom/style.css'
           )
diff --git a/spec/app/finders/main_theme/urls_in_404_page_spec.rb.rb b/spec/app/finders/main_theme/urls_in_404_page_spec.rb.rb
new file mode 100644
index 00000000..01cf483d
--- /dev/null
+++ b/spec/app/finders/main_theme/urls_in_404_page_spec.rb.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+describe WPScan::Finders::MainTheme::UrlsIn404Page do
+  subject(:finder) { described_class.new(target) }
+  let(:target)     { WPScan::Target.new(url) }
+  let(:url)        { 'http://wp.lab/' }
+  let(:fixtures)   { FINDERS_FIXTURES.join('main_theme', 'urls_in_404_page') }
+
+  # This stuff is just a child class of URLsInHomepage (using the error_404_res rather than homepage_res)
+  # which already has a spec
+end
diff --git a/spec/app/finders/main_theme/urls_in_homepage_spec.rb b/spec/app/finders/main_theme/urls_in_homepage_spec.rb
index 9f7565f9..314b63fb 100644
--- a/spec/app/finders/main_theme/urls_in_homepage_spec.rb
+++ b/spec/app/finders/main_theme/urls_in_homepage_spec.rb
@@ -6,7 +6,8 @@ describe WPScan::Finders::MainTheme::UrlsInHomepage do
   let(:url)        { 'http://wp.lab/' }
   let(:fixtures)   { FINDERS_FIXTURES.join('main_theme', 'urls_in_homepage') }
 
-  it_behaves_like 'App::Finders::WpItems::URLsInHomepage' do
+  it_behaves_like 'App::Finders::WpItems::UrlsInPage' do
+    let(:page_url)            { url }
     let(:type)                { 'themes' }
     let(:uniq_links)          { false }
     let(:uniq_codes)          { false }
@@ -18,6 +19,8 @@ describe WPScan::Finders::MainTheme::UrlsInHomepage do
     before do
       stub_request(:get, /.*.css/)
       stub_request(:get, target.url).to_return(body: File.read(fixtures.join('found.html')))
+
+      allow(target).to receive(:content_dir).and_return('wp-content')
     end
 
     it 'returns the expected Themes' do
diff --git a/spec/app/finders/main_theme/woo_framework_meta_generator_spec.rb b/spec/app/finders/main_theme/woo_framework_meta_generator_spec.rb
index e73d16b8..fc7f4f10 100644
--- a/spec/app/finders/main_theme/woo_framework_meta_generator_spec.rb
+++ b/spec/app/finders/main_theme/woo_framework_meta_generator_spec.rb
@@ -7,32 +7,50 @@ describe WPScan::Finders::MainTheme::WooFrameworkMetaGenerator do
   let(:fixtures)   { FINDERS_FIXTURES.join('main_theme', 'woo_framework_meta_generator') }
 
   describe '#passive' do
-    after do
-      stub_request(:get, url).to_return(body: File.read(fixtures.join(@file)))
-
-      expect(finder.passive).to eql @expected
+    before do
+      stub_request(:get, url).to_return(body: File.read(fixtures.join(homepage_fixture)))
+      stub_request(:get, ERROR_404_URL_PATTERN).to_return(body: File.read(fixtures.join(error_404_fixture)))
     end
 
     context 'when no Woo generator' do
+      let(:homepage_fixture) { 'no_woo_generator.html' }
+      let(:error_404_fixture) { 'no_woo_generator.html' }
+
       it 'returns nil' do
-        @file     = 'no_woo_generator.html'
-        @expected = nil
+        expect(finder.passive).to eql nil
       end
     end
 
     context 'when Woo generator' do
       before do
-        expect(target).to receive(:content_dir).at_least(1).and_return('wp-content')
+        allow(target).to receive(:content_dir).and_return('wp-content')
         stub_request(:get, "#{url}wp-content/themes/Merchant/style.css")
       end
 
-      it 'returns the expected theme' do
-        @file     = 'woo_generator.html'
-        @expected = WPScan::Model::Theme.new(
-          'Merchant', target,
-          found_by: 'Woo Framework Meta Generator (Passive Detection)',
-          confidence: 80
-        )
+      context 'from the homepage' do
+        let(:homepage_fixture) { 'woo_generator.html' }
+        let(:error_404_fixture) { 'no_woo_generator.html' }
+
+        it 'returns the expected theme' do
+          expect(finder.passive).to eql WPScan::Model::Theme.new(
+            'Merchant', target,
+            found_by: 'Woo Framework Meta Generator (Passive Detection)',
+            confidence: 80
+          )
+        end
+      end
+
+      context 'from the 404 page' do
+        let(:homepage_fixture) { 'no_woo_generator.html' }
+        let(:error_404_fixture) { 'woo_generator.html' }
+
+        it 'returns the expected theme' do
+          expect(finder.passive).to eql WPScan::Model::Theme.new(
+            'Merchant', target,
+            found_by: 'Woo Framework Meta Generator (Passive Detection)',
+            confidence: 80
+          )
+        end
       end
     end
   end
diff --git a/spec/app/finders/main_theme_spec.rb b/spec/app/finders/main_theme_spec.rb
index 11037430..a047c50b 100644
--- a/spec/app/finders/main_theme_spec.rb
+++ b/spec/app/finders/main_theme_spec.rb
@@ -8,7 +8,7 @@ describe WPScan::Finders::MainTheme::Base do
   describe '#finders' do
     it 'contains the expected finders' do
       expect(main_theme.finders.map { |f| f.class.to_s.demodulize })
-        .to eq %w[CssStyle WooFrameworkMetaGenerator UrlsInHomepage]
+        .to eq %w[CssStyleInHomepage CssStyleIn404Page WooFrameworkMetaGenerator UrlsInHomepage UrlsIn404Page]
     end
   end
 end
diff --git a/spec/app/finders/plugins/urls_in_404_page_spec.rb b/spec/app/finders/plugins/urls_in_404_page_spec.rb
new file mode 100644
index 00000000..f698c53c
--- /dev/null
+++ b/spec/app/finders/plugins/urls_in_404_page_spec.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+describe WPScan::Finders::Plugins::UrlsIn404Page do
+  subject(:finder) { described_class.new(target) }
+  let(:target)     { WPScan::Target.new(url) }
+  let(:url)        { 'https://wp.lab/' }
+  let(:fixtures)   { FINDERS_FIXTURES.join('plugins', 'urls_in_404_page') }
+
+  # This stuff is just a child class of URLsInHomepage (using the error_404_res rather than homepage_res)
+  # which already has a spec
+end
diff --git a/spec/app/finders/plugins/urls_in_homepage_spec.rb b/spec/app/finders/plugins/urls_in_homepage_spec.rb
index 225eb12f..5087733a 100644
--- a/spec/app/finders/plugins/urls_in_homepage_spec.rb
+++ b/spec/app/finders/plugins/urls_in_homepage_spec.rb
@@ -8,7 +8,8 @@ describe WPScan::Finders::Plugins::UrlsInHomepage do
 
   before { target.scope << 'sub.lab' }
 
-  it_behaves_like 'App::Finders::WpItems::URLsInHomepage' do
+  it_behaves_like 'App::Finders::WpItems::UrlsInPage' do
+    let(:page_url)            { url }
     let(:type)                { 'plugins' }
     let(:uniq_links)          { true }
     let(:uniq_codes)          { true }
diff --git a/spec/app/finders/plugins_spec.rb b/spec/app/finders/plugins_spec.rb
index fea6b1b5..6b93e61a 100644
--- a/spec/app/finders/plugins_spec.rb
+++ b/spec/app/finders/plugins_spec.rb
@@ -8,7 +8,7 @@ describe WPScan::Finders::Plugins::Base do
   describe '#finders' do
     it 'contains the expected finders' do
       expect(plugins.finders.map { |f| f.class.to_s.demodulize })
-        .to eq %w[UrlsInHomepage HeaderPattern Comment Xpath BodyPattern JavascriptVar KnownLocations]
+        .to eq %w[UrlsInHomepage UrlsIn404Page HeaderPattern Comment Xpath BodyPattern JavascriptVar KnownLocations]
     end
   end
 end
diff --git a/spec/app/finders/themes/urls_in_404_page_spec.rb b/spec/app/finders/themes/urls_in_404_page_spec.rb
new file mode 100644
index 00000000..fc723894
--- /dev/null
+++ b/spec/app/finders/themes/urls_in_404_page_spec.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+describe WPScan::Finders::Themes::UrlsIn404Page do
+  subject(:finder) { described_class.new(target) }
+  let(:target)     { WPScan::Target.new(url) }
+  let(:url)        { 'http://wp.lab/' }
+  let(:fixtures)   { FINDERS_FIXTURES.join('themes', 'urls_in_404_page') }
+
+  # This stuff is just a child class of URLsInHomepage (using the error_404_res rather than homepage_res)
+  # which already has a spec
+end
diff --git a/spec/app/finders/themes/urls_in_homepage_spec.rb b/spec/app/finders/themes/urls_in_homepage_spec.rb
index d6b152bb..6f5aa052 100644
--- a/spec/app/finders/themes/urls_in_homepage_spec.rb
+++ b/spec/app/finders/themes/urls_in_homepage_spec.rb
@@ -8,7 +8,8 @@ describe WPScan::Finders::Themes::UrlsInHomepage do
 
   # before { target.scope << 'sub.lab' }
 
-  it_behaves_like 'App::Finders::WpItems::URLsInHomepage' do
+  it_behaves_like 'App::Finders::WpItems::UrlsInPage' do
+    let(:page_url)            { url }
     let(:type)                { 'themes' }
     let(:uniq_links)          { true }
     let(:uniq_codes)          { true }
diff --git a/spec/app/finders/themes_spec.rb b/spec/app/finders/themes_spec.rb
index 7b033c57..a4f75e3e 100644
--- a/spec/app/finders/themes_spec.rb
+++ b/spec/app/finders/themes_spec.rb
@@ -8,7 +8,7 @@ describe WPScan::Finders::Themes::Base do
   describe '#finders' do
     it 'contains the expected finders' do
       expect(themes.finders.map { |f| f.class.to_s.demodulize })
-        .to eq %w[UrlsInHomepage KnownLocations]
+        .to eq %w[UrlsInHomepage UrlsIn404Page KnownLocations]
     end
   end
 end
diff --git a/spec/app/finders/users/wp_json_api_spec.rb b/spec/app/finders/users/wp_json_api_spec.rb
index e24af419..a9af123e 100644
--- a/spec/app/finders/users/wp_json_api_spec.rb
+++ b/spec/app/finders/users/wp_json_api_spec.rb
@@ -87,6 +87,8 @@ describe WPScan::Finders::Users::WpJsonApi do
   describe '#api_url' do
     let(:fixtures) { super().join('api_url') }
 
+    before { allow(target).to receive(:sub_dir).and_return(false) }
+
     context 'when url in the homepage' do
       {
         in_scope: 'https://wp.lab/wp-json/wp/v2/users/',
@@ -100,7 +102,7 @@ describe WPScan::Finders::Users::WpJsonApi do
       end
 
       context 'when subdir' do
-        before { allow(target).to receive(:subdir).and_return('cms') }
+        before { allow(target).to receive(:sub_dir).and_return('cms') }
 
         {
           in_scope_subdir: 'https://wp.lab/cms/wp-json/wp/v2/users/',
diff --git a/spec/fixtures/finders/main_theme/css_style/link_href.html b/spec/fixtures/finders/main_theme/css_style_in_homepage/link_href.html
similarity index 100%
rename from spec/fixtures/finders/main_theme/css_style/link_href.html
rename to spec/fixtures/finders/main_theme/css_style_in_homepage/link_href.html
diff --git a/spec/fixtures/finders/main_theme/css_style/no_in_scope_style.html b/spec/fixtures/finders/main_theme/css_style_in_homepage/no_in_scope_style.html
similarity index 100%
rename from spec/fixtures/finders/main_theme/css_style/no_in_scope_style.html
rename to spec/fixtures/finders/main_theme/css_style_in_homepage/no_in_scope_style.html
diff --git a/spec/fixtures/finders/main_theme/css_style/style_code.html b/spec/fixtures/finders/main_theme/css_style_in_homepage/style_code.html
similarity index 100%
rename from spec/fixtures/finders/main_theme/css_style/style_code.html
rename to spec/fixtures/finders/main_theme/css_style_in_homepage/style_code.html
diff --git a/spec/lib/finders/dynamic_finder/plugin_version_spec.rb b/spec/lib/finders/dynamic_finder/plugin_version_spec.rb
index 8fa96ff8..04bce07c 100644
--- a/spec/lib/finders/dynamic_finder/plugin_version_spec.rb
+++ b/spec/lib/finders/dynamic_finder/plugin_version_spec.rb
@@ -38,13 +38,21 @@ WPScan::DB::DynamicFinders::Plugin.versions_finders_configs.each do |slug, confi
         end
       end
 
-      let(:stubbed_response) { { body: 'aa' } }
+      before { allow(target).to receive(:content_dir).and_return('wp-content') }
 
       describe '#passive', slow: true do
         before do
-          stub_request(:get, target.url).to_return(stubbed_response)
+          if defined?(stubbed_homepage_res)
+            stub_request(:get, target.url).to_return(stubbed_homepage_res)
+          else
+            stub_request(:get, target.url)
+          end
 
-          expect(target).to receive(:content_dir).at_least(1).and_return('wp-content')
+          if defined?(stubbed_404_res)
+            stub_request(:get, ERROR_404_URL_PATTERN).to_return(stubbed_404_res)
+          else
+            stub_request(:get, ERROR_404_URL_PATTERN)
+          end
         end
 
         if config['path']
@@ -56,27 +64,63 @@ WPScan::DB::DynamicFinders::Plugin.versions_finders_configs.each do |slug, confi
         else
           context 'when no PATH' do
             context 'when the version is detected' do
-              let(:stubbed_response) do
-                df_stubbed_response(
-                  fixtures.join("#{finder_super_class.underscore}_passive_all.html"),
-                  finder_super_class
-                )
+              context 'from the homepage' do
+                let(:ie_url) { target.url }
+                let(:stubbed_homepage_res) do
+                  df_stubbed_response(
+                    fixtures.join("#{finder_super_class.underscore}_passive_all.html"),
+                    finder_super_class
+                  )
+                end
+
+                it 'returns the expected version/s' do
+                  found = [*finder.passive]
+
+                  expect(found).to_not be_empty
+
+                  found.each_with_index do |version, index|
+                    expected_version = expected.at(index)
+                    expected_ie = expected_version['interesting_entries'].map do |ie|
+                      ie.gsub(target.url + ',', ie_url + ',')
+                    end
+
+                    expect(version).to be_a WPScan::Model::Version
+                    expect(version.number).to eql expected_version['number'].to_s
+                    expect(version.found_by).to eql expected_version['found_by']
+                    expect(version.interesting_entries).to match_array expected_ie
+
+                    expect(version.confidence).to eql expected_version['confidence'] if expected_version['confidence']
+                  end
+                end
               end
 
-              it 'returns the expected version/s from the homepage' do
-                found = [*finder.passive]
+              context 'from the 404' do
+                let(:ie_url) { target.error_404_url }
+                let(:stubbed_404_res) do
+                  df_stubbed_response(
+                    fixtures.join("#{finder_super_class.underscore}_passive_all.html"),
+                    finder_super_class
+                  )
+                end
 
-                expect(found).to_not be_empty
+                it 'returns the expected version/s' do
+                  found = [*finder.passive]
 
-                found.each_with_index do |version, index|
-                  expected_version = expected.at(index)
+                  expect(found).to_not be_empty
 
-                  expect(version).to be_a WPScan::Model::Version
-                  expect(version.number).to eql expected_version['number'].to_s
-                  expect(version.found_by).to eql expected_version['found_by']
-                  expect(version.interesting_entries).to match_array expected_version['interesting_entries']
+                  found.each_with_index do |version, index|
+                    expected_version = expected.at(index)
+                    expected_ie = expected_version['interesting_entries'].map do |ie|
+                      ie.gsub(target.url + ',', ie_url + ',')
+                    end
 
-                  expect(version.confidence).to eql expected_version['confidence'] if expected_version['confidence']
+                    expect(version).to be_a WPScan::Model::Version
+                    expect(version.number).to eql expected_version['number'].to_s
+                    expect(version.found_by).to eql expected_version['found_by']
+                    expect(version.interesting_entries).to match_array expected_ie
+
+                    expect(version.confidence).to eql expected_version['confidence'] if expected_version['confidence']
+                  end
                 end
               end
             end
@@ -91,11 +135,10 @@ WPScan::DB::DynamicFinders::Plugin.versions_finders_configs.each do |slug, confi
       end
 
       describe '#aggressive' do
-        let(:fixtures) { super().join(slug, finder_class.underscore) }
+        let(:fixtures)         { super().join(slug, finder_class.underscore) }
+        let(:stubbed_response) { { body: 'aa' } }
 
         before do
-          expect(target).to receive(:content_dir).at_least(1).and_return('wp-content')
-
           stub_request(:get, plugin.url(config['path'])).to_return(stubbed_response) if config['path']
         end
 
diff --git a/spec/lib/finders/dynamic_finder/theme_version_spec.rb b/spec/lib/finders/dynamic_finder/theme_version_spec.rb
index 6ae926e5..4482c6a0 100644
--- a/spec/lib/finders/dynamic_finder/theme_version_spec.rb
+++ b/spec/lib/finders/dynamic_finder/theme_version_spec.rb
@@ -38,8 +38,6 @@ WPScan::DB::DynamicFinders::Theme.versions_finders_configs.each do |slug, config
         end
       end
 
-      let(:stubbed_response) { { body: 'aa' } }
-
       before do
         allow(target).to receive(:content_dir).and_return('wp-content')
 
@@ -48,7 +46,19 @@ WPScan::DB::DynamicFinders::Theme.versions_finders_configs.each do |slug, config
       end
 
       describe '#passive', slow: true do
-        before { stub_request(:get, target.url).to_return(stubbed_response) }
+        before do
+          if defined?(stubbed_homepage_res)
+            stub_request(:get, target.url).to_return(stubbed_homepage_res)
+          else
+            stub_request(:get, target.url)
+          end
+
+          if defined?(stubbed_404_res)
+            stub_request(:get, ERROR_404_URL_PATTERN).to_return(stubbed_404_res)
+          else
+            stub_request(:get, ERROR_404_URL_PATTERN)
+          end
+        end
 
         if config['path']
           context 'when PATH' do
@@ -59,27 +69,63 @@ WPScan::DB::DynamicFinders::Theme.versions_finders_configs.each do |slug, config
         else
           context 'when no PATH' do
             context 'when the version is detected' do
-              let(:stubbed_response) do
-                df_stubbed_response(
-                  fixtures.join("#{finder_super_class.underscore}_passive_all.html"),
-                  finder_super_class
-                )
+              context 'from the homepage' do
+                let(:ie_url) { target.url }
+                let(:stubbed_homepage_res) do
+                  df_stubbed_response(
+                    fixtures.join("#{finder_super_class.underscore}_passive_all.html"),
+                    finder_super_class
+                  )
+                end
+
+                it 'returns the expected version/s' do
+                  found = [*finder.passive]
+
+                  expect(found).to_not be_empty
+
+                  found.each_with_index do |version, index|
+                    expected_version = expected.at(index)
+                    expected_ie = expected_version['interesting_entries'].map do |ie|
+                      ie.gsub(target.url + ',', ie_url + ',')
+                    end
+
+                    expect(version).to be_a WPScan::Model::Version
+                    expect(version.number).to eql expected_version['number'].to_s
+                    expect(version.found_by).to eql expected_version['found_by']
+                    expect(version.interesting_entries).to match_array expected_ie
+
+                    expect(version.confidence).to eql expected_version['confidence'] if expected_version['confidence']
+                  end
+                end
               end
 
-              it 'returns the expected version/s from the homepage' do
-                found = [*finder.passive]
+              context 'from the 404' do
+                let(:ie_url) { target.error_404_url }
+                let(:stubbed_404_res) do
+                  df_stubbed_response(
+                    fixtures.join("#{finder_super_class.underscore}_passive_all.html"),
+                    finder_super_class
+                  )
+                end
 
-                expect(found).to_not be_empty
+                it 'returns the expected version/s' do
+                  found = [*finder.passive]
 
-                found.each_with_index do |version, index|
-                  expected_version = expected.at(index)
+                  expect(found).to_not be_empty
 
-                  expect(version).to be_a WPScan::Model::Version
-                  expect(version.number).to eql expected_version['number'].to_s
-                  expect(version.found_by).to eql expected_version['found_by']
-                  expect(version.interesting_entries).to match_array expected_version['interesting_entries']
+                  found.each_with_index do |version, index|
+                    expected_version = expected.at(index)
+                    expected_ie = expected_version['interesting_entries'].map do |ie|
+                      ie.gsub(target.url + ',', ie_url + ',')
+                    end
 
-                  expect(version.confidence).to eql expected_version['confidence'] if expected_version['confidence']
+                    expect(version).to be_a WPScan::Model::Version
+                    expect(version.number).to eql expected_version['number'].to_s
+                    expect(version.found_by).to eql expected_version['found_by']
+                    expect(version.interesting_entries).to match_array expected_ie
+
+                    expect(version.confidence).to eql expected_version['confidence'] if expected_version['confidence']
+                  end
                 end
               end
             end
@@ -94,7 +140,8 @@ WPScan::DB::DynamicFinders::Theme.versions_finders_configs.each do |slug, config
       end
 
       describe '#aggressive' do
-        let(:fixtures) { super().join(slug, finder_class.underscore) }
+        let(:fixtures)         { super().join(slug, finder_class.underscore) }
+        let(:stubbed_response) { { body: 'aa' } }
 
         before do
           stub_request(:get, theme.url(config['path'])).to_return(stubbed_response) if config['path']
diff --git a/spec/lib/finders/dynamic_finder/wp_version_spec.rb b/spec/lib/finders/dynamic_finder/wp_version_spec.rb
index 1a7f5fd4..29161120 100644
--- a/spec/lib/finders/dynamic_finder/wp_version_spec.rb
+++ b/spec/lib/finders/dynamic_finder/wp_version_spec.rb
@@ -25,7 +25,10 @@ WPScan::DB::DynamicFinders::Wordpress.versions_finders_configs.each do |finder_c
     let(:stubbed_response) { { body: '' } }
 
     describe '#passive' do
-      before { stub_request(:get, target.url).to_return(stubbed_response) }
+      before do
+        stub_request(:get, target.url).to_return(stubbed_response)
+        stub_request(:get, ERROR_404_URL_PATTERN)
+      end
 
       if config['path']
         context 'when PATH' do
@@ -66,7 +69,7 @@ WPScan::DB::DynamicFinders::Wordpress.versions_finders_configs.each do |finder_c
       let(:fixtures) { super().join(finder_class.underscore) }
 
       before do
-        allow(target).to receive(:sub_dir).and_return(nil)
+        allow(target).to receive(:sub_dir).and_return(false)
 
         stub_request(:get, target.url(config['path'])).to_return(stubbed_response) if config['path']
       end
diff --git a/spec/shared_examples.rb b/spec/shared_examples.rb
index 526acb76..3a88dfbc 100644
--- a/spec/shared_examples.rb
+++ b/spec/shared_examples.rb
@@ -5,6 +5,6 @@ require 'shared_examples/views/wp_version'
 require 'shared_examples/views/main_theme'
 require 'shared_examples/views/enumeration'
 require 'shared_examples/target/platform/wordpress'
-require 'shared_examples/finders/wp_items/urls_in_homepage'
+require 'shared_examples/finders/wp_items/urls_in_page'
 require 'shared_examples/references'
 require 'shared_examples/dynamic_finders/wp_items'
diff --git a/spec/shared_examples/dynamic_finders/wp_items.rb b/spec/shared_examples/dynamic_finders/wp_items.rb
index 8d998a56..c30c6b18 100644
--- a/spec/shared_examples/dynamic_finders/wp_items.rb
+++ b/spec/shared_examples/dynamic_finders/wp_items.rb
@@ -16,13 +16,15 @@ shared_examples WPScan::Finders::DynamicFinder::WpItems::Finder do
 
   describe '#passive' do
     before do
-      stub_request(:get, target.url).to_return(body: body)
+      stub_request(:get, target.url).to_return(body: homepage_body)
+      stub_request(:get, ERROR_404_URL_PATTERN).to_return(body: error_404_body)
 
       allow(target).to receive(:content_dir).and_return('wp-content')
     end
 
     context 'when no matches' do
-      let(:body) { '' }
+      let(:homepage_body) { '' }
+      let(:error_404_body) { '' }
 
       it 'returns an empty array' do
         expect(finder.passive).to eql([])
@@ -30,9 +32,7 @@ shared_examples WPScan::Finders::DynamicFinder::WpItems::Finder do
     end
 
     context 'when matches' do
-      let(:body) { File.read(passive_fixture) }
-
-      it 'contains the expected items' do
+      let(:expected_items) do
         expected = []
 
         finder.passive_configs.each do |slug, configs|
@@ -48,7 +48,25 @@ shared_examples WPScan::Finders::DynamicFinder::WpItems::Finder do
           end
         end
 
-        expect(finder.passive).to match_array(expected.map { |item| eql(item) })
+        expected
+      end
+
+      context 'from the homepage' do
+        let(:homepage_body) { File.read(passive_fixture) }
+        let(:error_404_body) { '' }
+
+        it 'contains the expected items' do
+          expect(finder.passive).to match_array(expected_items.map { |item| eql(item) })
+        end
+      end
+
+      context 'from the 404' do
+        let(:homepage_body) { '' }
+        let(:error_404_body) { File.read(passive_fixture) }
+
+        it 'contains the expected items' do
+          expect(finder.passive).to match_array(expected_items.map { |item| eql(item) })
+        end
       end
     end
   end
diff --git a/spec/shared_examples/finders/wp_items/urls_in_homepage.rb b/spec/shared_examples/finders/wp_items/urls_in_page.rb
similarity index 88%
rename from spec/shared_examples/finders/wp_items/urls_in_homepage.rb
rename to spec/shared_examples/finders/wp_items/urls_in_page.rb
index d2b934c1..b3598a24 100644
--- a/spec/shared_examples/finders/wp_items/urls_in_homepage.rb
+++ b/spec/shared_examples/finders/wp_items/urls_in_page.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
 
-shared_examples 'App::Finders::WpItems::URLsInHomepage' do
+shared_examples 'App::Finders::WpItems::UrlsInPage' do
   before do
-    stub_request(:get, finder.target.url).to_return(body: File.read(fixtures.join(file)))
+    stub_request(:get, page_url).to_return(body: File.read(fixtures.join(file)))
   end
 
   describe '#items_from_links' do
diff --git a/spec/shared_examples/target/platform/wordpress.rb b/spec/shared_examples/target/platform/wordpress.rb
index 3088ffae..32432996 100644
--- a/spec/shared_examples/target/platform/wordpress.rb
+++ b/spec/shared_examples/target/platform/wordpress.rb
@@ -7,14 +7,17 @@ shared_examples WPScan::Target::Platform::WordPress do
 
   let(:fixtures) { FIXTURES.join('target', 'platform', 'wordpress') }
 
-  describe '#wordpress?' do
+  describe '#wordpress?, wordpress_from_meta_comments_or_scripts?' do
     let(:fixtures) { super().join('detection') }
 
     before do
       stub_request(:get, target.url).to_return(body: File.read(fixtures.join("#{homepage}.html")))
+      stub_request(:get, ERROR_404_URL_PATTERN).to_return(body: File.read(fixtures.join("#{page_404}.html")))
     end
 
     context 'when pattern/s in the homepage' do
+      let(:page_404) { 'not_wp' }
+
       %w[default wp_includes only_scripts meta_generator comments mu_plugins wp_admin wp_json_oembed].each do |file|
         context "when a wordpress page (#{file}.html)" do
           let(:homepage) { file }
@@ -29,39 +32,55 @@ shared_examples WPScan::Target::Platform::WordPress do
     context 'when no clues in the homepage' do
       let(:homepage) { 'not_wp' }
 
-      context 'when only passive detection mode' do
-        it 'returns false' do
-          expect(subject.wordpress?(:passive)).to be false
+      context 'when pattern/s in the 404 page' do
+        %w[default wp_includes only_scripts meta_generator comments mu_plugins wp_admin wp_json_oembed].each do |file|
+          context "when a wordpress page (#{file}.html)" do
+            let(:page_404) { file }
+
+            it 'returns true' do
+              expect(subject.wordpress?(:mixed)).to be true
+            end
+          end
         end
       end
 
-      context 'when mixed or aggressive detection modes' do
-        context 'when wp-admin/install.php and wp-login.php not there' do
+      context 'when no clues in the 404 page' do
+        let(:page_404) { 'not_wp' }
+
+        context 'when only passive detection mode' do
           it 'returns false' do
-            %w[wp-admin/install.php wp-login.php].each do |path|
-              stub_request(:get, target.url(path)).to_return(status: 404)
+            expect(subject.wordpress?(:passive)).to be false
+          end
+        end
+
+        context 'when mixed or aggressive detection modes' do
+          context 'when wp-admin/install.php and wp-login.php not there' do
+            it 'returns false' do
+              %w[wp-admin/install.php wp-login.php].each do |path|
+                stub_request(:get, target.url(path)).to_return(status: 404)
+              end
+
+              expect(subject.wordpress?(:mixed)).to be false
             end
-
-            expect(subject.wordpress?(:mixed)).to be false
           end
-        end
 
-        context 'when wp-admin/install.php is matching a WP install' do
-          it 'returns true' do
-            stub_request(:get, target.url('wp-admin/install.php'))
-              .to_return(body: File.read(fixtures.join('wp-admin-install.php')))
+          context 'when wp-admin/install.php is matching a WP install' do
+            it 'returns true' do
+              stub_request(:get, target.url('wp-admin/install.php'))
+                .to_return(body: File.read(fixtures.join('wp-admin-install.php')))
 
-            expect(subject.wordpress?(:mixed)).to be true
+              expect(subject.wordpress?(:mixed)).to be true
+            end
           end
-        end
 
-        context 'when wp-admin/install.php not there but wp-login.php is matching a WP install' do
-          it 'returns true' do
-            stub_request(:get, target.url('wp-admin/install.php')).to_return(status: 404)
-            stub_request(:get, target.url('wp-login.php'))
-              .to_return(body: File.read(fixtures.join('wp-login.php')))
+          context 'when wp-admin/install.php not there but wp-login.php is matching a WP install' do
+            it 'returns true' do
+              stub_request(:get, target.url('wp-admin/install.php')).to_return(status: 404)
+              stub_request(:get, target.url('wp-login.php'))
+                .to_return(body: File.read(fixtures.join('wp-login.php')))
 
-            expect(subject.wordpress?(:mixed)).to be true
+              expect(subject.wordpress?(:mixed)).to be true
+            end
           end
         end
       end
diff --git a/spec/shared_examples/target/platform/wordpress/custom_directories.rb b/spec/shared_examples/target/platform/wordpress/custom_directories.rb
index ce4d354c..e822c263 100644
--- a/spec/shared_examples/target/platform/wordpress/custom_directories.rb
+++ b/spec/shared_examples/target/platform/wordpress/custom_directories.rb
@@ -4,6 +4,9 @@ shared_examples 'WordPress::CustomDirectories' do
   let(:fixtures) { super().join('custom_directories') }
 
   describe '#content_dir' do
+    # Stub the error_404_res to make it easier to test
+    before { stub_request(:get, ERROR_404_URL_PATTERN) }
+
     {
       default: 'wp-content', https: 'wp-content', custom_w_spaces: 'custom content spaces',
       relative_one: 'wp-content', relative_two: 'wp-content', cache: 'wp-content',
@@ -45,9 +48,9 @@ shared_examples 'WordPress::CustomDirectories' do
       end
     end
 
-    context 'when not found via the homepage' do
+    context 'when not found via the homepage or 404' do
       before do
-        stub_request(:get, target.url).to_return(body: '')
+        stub_request(:get, target.url)
 
         expect(target).to receive(:default_content_dir_exists?).and_return(dir_exist)
       end
@@ -123,6 +126,9 @@ shared_examples 'WordPress::CustomDirectories' do
   end
 
   describe '#sub_dir' do
+    # Stub the error_404_res to make it easier to test
+    before { stub_request(:get, ERROR_404_URL_PATTERN) }
+
     { default: false, with_sub_dir: 'wp', relative_two_sub_dir: 'cms' }.each do |file, expected|
       it "returns #{expected} for #{file}.html" do
         fixture = File.join(fixtures, "#{file}.html")
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 9dfe59b1..16218e07 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -102,5 +102,6 @@ SPECS                    = Pathname.new(__FILE__).dirname
 FIXTURES                 = SPECS.join('fixtures')
 FINDERS_FIXTURES         = FIXTURES.join('finders')
 DYNAMIC_FINDERS_FIXTURES = FIXTURES.join('dynamic_finders')
+ERROR_404_URL_PATTERN    = %r{/[a-z\d]{7}\.html$}
 
 redefine_constant(:DB_DIR, FIXTURES.join('db'))