As described in Robert Zehnder's "Adding new sites to Railo demystified", I needed to also add the new site to Railo's server.xml file:
<Host name="awesome.site.com" appBase="webapps">
<Context path="" docBase="/var/www/awesome/" />
</Host>
It was also key to make sure the Railo user had permissions to /var/www/awesome/
so that Railo could create the WEB-INF
folder.