Thanks! I was able to fix it by moving the handle_errors block to the root of the site block and duplicating the path matching inside it.
handle_errors {
@romans404 {
path /romans/*
expression `{http.error.status_code} == 404`
}
route @romans404 {
root content/romans-pizza/public/
try_files @404 /404.html
file_server
}
}