1. Just a heads up that twebserver 1.47.35 is out that fixes many previous issues and has new features:
https://github.com/jerily/twebserver2. All feedback is welcome.
3. You might want to try the following:
proc open_conn {} {
set sock [socket localhost 8080]
puts -nonewline $sock whatever
}while {true} { catch {open_conn} }