Indeed.
Since you work in network engineering maybe you'd know the answer. I've googled and failed to find a satisfactory answer.
Apparently you can run a VPN within a SSL tunnel. As such assuming you use port 443 would you be able to see its a VPN connection within? I would assume the SSL would hide the VPN within but my knowledge is limited on this.
Just wondering if it's possible to remove the VPN suspicion as well.
VPNception?

Not sure to be honest. That sounds a bit pointless. There's some very smart kit out there these days that's designed to figure out what the connection is doing rather than blindly allowing/denying traffic by port. I wonder if it'd pick up "tunnel within a tunnel". Might have to ask one of my more clever colleagues!
I'd imagine such a long-lived SSL connection would be treated with similar suspicion to a VPN. I did some experimentation running mine on different ports to see if there was any performance difference but can't remember what the results were now. I assume I ended up running 443/UDP for a reason.
As long as you're not doing anything illegal I wouldn't worry. The idea is to make it a massive pain in the rear for the authorities as a point of principle IMO.

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