diff --git a/plugins/guests/debian/cap/change_host_name.rb b/plugins/guests/debian/cap/change_host_name.rb
index 2107ea9e4..118592c27 100644
--- a/plugins/guests/debian/cap/change_host_name.rb
+++ b/plugins/guests/debian/cap/change_host_name.rb
@@ -20,11 +20,11 @@ module VagrantPlugins
               comm.sudo("sed -i 's/.*$/#{name.split('.')[0]}/' /etc/hostname")
 
               # hosts should resemble:
+              # 127.0.0.1   localhost host.fqdn.com host
               # 127.0.1.1   host.fqdn.com host
               # First to set fqdn
-              comm.sudo("sed -i 's@#{old}@#{name}@' /etc/hosts")
-              # Second to set hostname
-              comm.sudo("sed -i 's@#{old.split('.')[0]}@#{name.split('.')[0]}@' /etc/hosts")
+              comm.sudo("sed -ri 's@^(([0-9]{1,3}\.){3}[0-9]{1,3})\\s+(localhost)\\b.*$@\\1\\t#{name} #{name.split('.')[0]} \\3@g' /etc/hosts")
+              comm.sudo("sed -ri 's@^(([0-9]{1,3}\.){3}[0-9]{1,3})\\s+(#{old.split('.')[0]})\\b.*$@\\1\\t#{name} #{name.split('.')[0]}@g' /etc/hosts")
 
               comm.sudo("hostname -F /etc/hostname")
               comm.sudo("hostname --fqdn > /etc/mailname")