Testing manually I find it opening a new session (refreshing/loading the page), then sending the HELLO and registering a channel succeeds three times. The fifth time the session is opened but when the HELLO message is sent it stops responding.

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.