Great question. For 'in flight' connections like a VPN, it is harder. I would most likely try to be "same network"... so I'd find them at a coffee shop and try

Great question. For 'in flight' connections like a VPN, it is harder. I would most likely try to be "same network"... so I'd find them at a coffee shop and try to compromise the dev machine on the network, social engineer/phish, or if the dev was at home and I needed in, I'd try to impersonate their home WAP, or I'd try compromise their machine to cross a tunnel or look for codebases, etc. Edit: Totally derailed the topic, my bad.