I’m on my phone so this will be brief. The short answer is no (in CommandBox 5). The longer answer is yes, in CommandBox 6. 6 has support for SSL SNI as well as multi-site support which basically does multiple contexts but with a proper mechanism for defining them directly in your server.json with host header matching as well as having ALL settings like rewrites, custom error pages, and unlimited http/s/ajp bindings per site. The only caveat is multi site is planned to be unlimited for development use and up to two sites in production. Unlimited production usage will be available via CommandBox Pro.