@zachdecook If I recall correct, I too was originally using #mod_http_upload but was given the suggestion on the Prosody chatroom to try out http_file_share. So far, I haven't had any issues but it's rare that I share files on XMPP. And for my use case, trunk has been pretty stable.
@samir the only trouble I've had so far is with sending attachments. Looks like you have #mod_http_file_share enabled (I'm not on trunk, but could use community #mod_http_upload for #XEP0363). I think this means the sysadmin could view any attachment? So I would want to wait for #XEP0454 in #prosody?