diff --git a/lib/install/dev.bat b/lib/install/dev.bat
new file mode 100644
index 00000000..c16867b9
--- /dev/null
+++ b/lib/install/dev.bat
@@ -0,0 +1,12 @@
+@echo off
+
+set gem_installed=
+
+for /f "delims=" %%a in ('gem list foreman -i') do @set gem_installed=%%a
+
+if %gem_installed%==false (
+  echo "Installing foreman..."
+  gem install foreman
+)
+
+foreman start -f Procfile.dev %*
\ No newline at end of file
diff --git a/lib/install/tailwindcss.rb b/lib/install/tailwindcss.rb
index 413f86b8..ebc95c67 100644
--- a/lib/install/tailwindcss.rb
+++ b/lib/install/tailwindcss.rb
@@ -39,10 +39,15 @@
 end
 
 if Rails.root.join("Procfile.dev").exist?
-  append_to_file "Procfile.dev", "css: bin/rails tailwindcss:watch\n"
+  unless Gem.win_platform?
+    append_to_file "Procfile.dev", "css: bin/rails tailwindcss:watch\n"
+  else
+    append_to_file "Procfile.dev", "css: ruby bin/rails tailwindcss:watch\n"
+  end
 else
   say "Add default Procfile.dev"
   copy_file "#{__dir__}/Procfile.dev", "Procfile.dev"
+  gsub_file "Procfile.dev", /bin\/rails/, "ruby bin/rails" if Gem.win_platform?
 
   say "Ensure foreman is installed"
   run "gem install foreman"
@@ -51,6 +56,7 @@
 say "Add bin/dev to start foreman"
 copy_file "#{__dir__}/dev", "bin/dev"
 chmod "bin/dev", 0755, verbose: false
+copy_file "#{__dir__}/dev.bat", "bin/dev.bat" if Gem.win_platform?
 
 say "Compile initial Tailwind build"
 run "rails tailwindcss:build"