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.