So this is interesting! And I think what happened to me the other day. During the same AR750 session (by that I mean without rebooting or powering it off) if I connect directly to OpenVPN first, disconnect, then connect using my profile that uses stunnel (OpenVPN config the same except it connects to the stunnel on 127.0.0.1), then it works! I’ve simulated it a few times now. If I unplug or reboot the AR750 and try connecting to stunnel first, traffic won’t pass. But if I connect to OpenVPN directly, then disconnect and reconnect using stunnel, it works.

I have no idea to begin understanding why that is happening. I am not changing anything other than the order in which I connect. The problem I’m going to have with that process is the other location I’m going to blocks OpenVPN hence the use of stunnel. Not sure if I’m going to be able to connect first on my cell phone hotspot, get connected to stunnel, disconnect from hotspot, reconnect to enterprise wifi and… work? shrug I will try it and report back.