diff --git a/lib/bootic_cli/commands/themes.rb b/lib/bootic_cli/commands/themes.rb
index 71ead81..04b9098 100644
--- a/lib/bootic_cli/commands/themes.rb
+++ b/lib/bootic_cli/commands/themes.rb
@@ -157,7 +157,7 @@ def watch
 
           write_lockfile
           at_exit { remove_lockfile }
-          workflows.watch(current_dir, remote_theme)
+          workflows.watch(current_dir, remote_theme, local_theme)
         end
       end
 
diff --git a/lib/bootic_cli/themes/workflows.rb b/lib/bootic_cli/themes/workflows.rb
index ee5ef59..9026432 100644
--- a/lib/bootic_cli/themes/workflows.rb
+++ b/lib/bootic_cli/themes/workflows.rb
@@ -189,7 +189,7 @@ def publish(local_theme, remote_theme)
         end
       end
 
-      def watch(dir, remote_theme, watcher: Listen)
+      def watch(dir, remote_theme, local_theme, watcher: Listen)
         listener = watcher.to(dir) do |modified, added, removed|
 
           if modified.any?
@@ -229,12 +229,31 @@ def watch(dir, remote_theme, watcher: Listen)
         }
 
         prompt.say "Preview changes at #{remote_theme.path} -- Hit Ctrl-C to stop watching for changes.", :cyan
+
+
+        if local_theme && File.exists?(File.join(dir, 'tailwind.config.js'))
+          source = local_theme.templates.find { |t| t.name['css'] && t.name['input'] }
+          target = local_theme.templates.find { |t| t.name['css'] && t.name['output'] }
+
+          if source && target
+            notice "Tailwind config found! Firing the CLI in watch mode.."
+            run_tailwind_cli(source, target) # blocks
+            return
+          else
+            notice "Tailwind config found, but couldn't determine the source/input and target/output files..."
+          end
+        end
+
         Kernel.sleep
       end
 
       private
       attr_reader :prompt
 
+      def run_tailwind_cli(source_css, target_css)
+        `npx tailwindcss -i #{source_css} -o #{target_css} --watch`
+      end
+
       def check_dupes!(list)
         names = list.map { |f| f.file_name.downcase }
         dupes = names.group_by { |e| e }.select { |k, v| v.size > 1 }.map(&:first)