diff --git a/bridgetown-core/lib/bridgetown-core/configurations/bt-postcss.rb b/bridgetown-core/lib/bridgetown-core/configurations/bt-postcss.rb
index 035831029..5f21ad8f0 100644
--- a/bridgetown-core/lib/bridgetown-core/configurations/bt-postcss.rb
+++ b/bridgetown-core/lib/bridgetown-core/configurations/bt-postcss.rb
@@ -13,12 +13,14 @@
   return
 end
 
+confirm = ask "This configuration will ovewrite your existing #{"postcss.config.js".bold.white}. Would you like to continue? [Yn]"
+return unless confirm.casecmp?("Y")
+
 plugins = %w(postcss-easy-import postcss-mixins postcss-color-function cssnano)
 
 say "Adding the following PostCSS plugins: #{plugins.join(' | ')}", :green
 run "yarn add -D #{plugins.join(' ')}"
 
-remove_file "postcss.config.js"
-copy_file "#{TEMPLATE_PATH}/postcss.config.js", "postcss.config.js"
+copy_file "#{TEMPLATE_PATH}/postcss.config.js", "postcss.config.js", force: true
 
 # rubocop:enable all
diff --git a/bridgetown-core/lib/bridgetown-core/configurations/tailwindcss.rb b/bridgetown-core/lib/bridgetown-core/configurations/tailwindcss.rb
index 77df059fe..cbb2c120d 100644
--- a/bridgetown-core/lib/bridgetown-core/configurations/tailwindcss.rb
+++ b/bridgetown-core/lib/bridgetown-core/configurations/tailwindcss.rb
@@ -1,5 +1,7 @@
 # frozen_string_literal: true
 
+# rubocop:disable all
+
 TEMPLATE_PATH = File.expand_path("./tailwindcss", __dir__)
 
 unless File.exist?("postcss.config.js")
@@ -11,13 +13,17 @@
   return
 end
 
+confirm = ask "This configuration will ovewrite your existing #{"postcss.config.js".bold.white}. Would you like to continue? [Yn]"
+return unless confirm.casecmp?("Y")
+
 run "yarn add -D tailwindcss"
 run "npx tailwindcss init"
 
-remove_file "postcss.config.js"
-copy_file "#{TEMPLATE_PATH}/postcss.config.js", "postcss.config.js"
+copy_file "#{TEMPLATE_PATH}/postcss.config.js", "postcss.config.js", force: true
 
 prepend_to_file "frontend/styles/index.css",
                 File.read("#{TEMPLATE_PATH}/css_imports.css")
 
 run "bundle exec bridgetown configure purgecss"
+
+# rubocop:enable all