diff --git a/Vagrantfile b/Vagrantfile
index 4997060552..29803603a0 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -29,7 +29,7 @@ Vagrant.configure('2') do |config|
   config.vm.box = box
   config.vm.box_version = vconfig.fetch('vagrant_box_version')
   config.ssh.forward_agent = true
-  config.vm.post_up_message = post_up_message
+  config.vm.post_up_message = post_up_message(trellis_config)
 
   # Fix for: "stdin: is not a tty"
   # https://github.com/mitchellh/vagrant/issues/1673#issuecomment-28288042
diff --git a/lib/trellis/vagrant.rb b/lib/trellis/vagrant.rb
index ef3c6bd13a..accbc6ceb9 100644
--- a/lib/trellis/vagrant.rb
+++ b/lib/trellis/vagrant.rb
@@ -72,7 +72,7 @@ def mount_options(mount_type, dmode:, fmode:)
   end
 end
 
-def post_up_message
+def post_up_message(trellis_config)
   msg = 'Your Trellis Vagrant box is ready to use!'
   msg << "\n* Composer and WP-CLI commands need to be run on the virtual machine"
   msg << "\n  for any post-provision modifications."
@@ -80,6 +80,21 @@ def post_up_message
   msg << "\n* Then navigate to your WordPress sites at `/srv/www`"
   msg << "\n  or to your Trellis files at `#{ANSIBLE_PATH_ON_VM}`."
 
+  if trellis_config.wordpress_sites.any?
+    msg << "\n\n\e[35m🚀 Development URLs: \e[0m"
+    trellis_config.wordpress_sites.each do |site_name, site|
+      site_url = site['site_hosts'].first
+      site_url = site_url.is_a?(Hash) ? site_url['canonical'] : site_url
+      site_url = site.dig('ssl', 'enabled') ? "https://#{site_url}" : "http://#{site_url}"
+      msg << "\n
+  🌱 \e[37mName:\e[33m #{site_name}\e[0m
+   ├── \e[37m🔗 URL:\e[33m #{site_url}\e[0m
+   ├── \e[37m🔧 Admin:\e[33m #{site_url}/wp-admin\e[0m
+   └── \e[37m📩 Mailpit:\e[33m #{site_url}:8025\e[0m
+    "
+    end
+  end
+
   msg
 end