I am facing the same issue as your. These are the exact steps I took and same behaviour.
I have followed these approaches so far:
Recreated the payload
Uploaded the payload
Restarted msf and the whole process
Restarted Kali then the whole process from scratch
Reconnected openvpn
Make sure that all the time I have connectivity
Make sure that I have access to ftp/IIS server
Nothing looks work.
The only thing I noticed was that if I use “run”, I get this same issue. If I use “exploit” (or “exploit -j”) it does not even start the reverse TCP handler part.
Confirm: Return to your terminal with your meterperter session. Otherwise, start the entire exploit over, end sessions and go step by step. Annoying, but necessary.
@JoyHuggs I’ve done exactly that, restart everything again but it keeos not working, what is odd is that I had a meterpreter session then it died and when I tried to restart the shell with a listener and refreshing the payloaf nothing happened from that moment onwards. On the other hand with a simple webshell everything works but for the training I’m trying to do I need the access to a meterpreter shell.
I ran into the same symptoms, for me the issue was that I hadn’t set the payload in the handler. It looks like the original poster has done that, but for anyone else who may end up here that might be worth checking