diff --git a/app/controllers/admin/sensitive_words_controller.rb b/app/controllers/admin/sensitive_words_controller.rb
index d97da2a927..eaa6ae802e 100644
--- a/app/controllers/admin/sensitive_words_controller.rb
+++ b/app/controllers/admin/sensitive_words_controller.rb
@@ -11,6 +11,14 @@ module Admin
     def create
       authorize :sensitive_words, :create?
 
+      begin
+        test_words
+      rescue
+        flash[:alert] = I18n.t('admin.ng_words.test_error')
+        redirect_to after_update_redirect_path
+        return
+      end
+
       @admin_settings = Form::AdminSettings.new(settings_params)
 
       if @admin_settings.save
@@ -23,6 +31,12 @@ module Admin
 
     private
 
+    def test_words
+      sensitive_words = settings_params['sensitive_words'].split(/\r\n|\r|\n/)
+      sensitive_words_for_full = settings_params['sensitive_words_for_full'].split(/\r\n|\r|\n/)
+      Admin::NgWord.reject_with_custom_words?('Sample text', sensitive_words + sensitive_words_for_full)
+    end
+
     def after_update_redirect_path
       admin_sensitive_words_path
     end
diff --git a/app/models/admin/sensitive_word.rb b/app/models/admin/sensitive_word.rb
index 0e4f3e6a16..ab457382b9 100644
--- a/app/models/admin/sensitive_word.rb
+++ b/app/models/admin/sensitive_word.rb
@@ -4,8 +4,8 @@ class Admin::SensitiveWord
   class << self
     def sensitive?(text, spoiler_text)
       exposure_text = (spoiler_text.presence || text)
-      (spoiler_text.blank? && sensitive_words.any? { |word| text.include?(word) }) ||
-        sensitive_words_for_full.any? { |word| exposure_text.include?(word) }
+      (spoiler_text.blank? && sensitive_words.any? { |word| include?(text, word) }) ||
+        sensitive_words_for_full.any? { |word| include?(exposure_text, word) }
     end
 
     def modified_text(text, spoiler_text)
@@ -14,6 +14,14 @@ class Admin::SensitiveWord
 
     private
 
+    def include?(text, word)
+      if word.start_with?('?') && word.size >= 2
+        text =~ /#{word[1..]}/i
+      else
+        text.include?(word)
+      end
+    end
+
     def sensitive_words
       Setting.sensitive_words || []
     end