Testing manually I find it opening a new session (refreshing/loading the page), then sending the HELLO and the reload, this will succeed four times. The fifth time the session is opened but when the HELLO message is sent it stops responding. This seems to be consistent as far as I can tell.

I was thinking that perhaps we could add a cron job:
Add cron to the cartridge:

rhc cartridge add cron-1.4 -a timeout

Create a file named .openshift/cron/minutely/wakeup with the following contents:

#!/usr/bin/env python
import getpass
import sys 
import telnetlib

tn = telnetlib.Telnet("localhost", 8000)
tn.write("GET /simplepush HTTP/1.1\n")
tn.write("HOST bogus.com\n")
tn.write("\n")
tn.write("\n")
tn.write("exit\n")

Having this run a a one minute interval is too long but at least it might help a little during development. Perhaps if we could get it to run every second it might be a temp workaround.