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What if I use a VPN inside a cloud VM and scp the files? Would that raise any flags?
VPN usage is simple to detect. I don’t know how SA deals with it. If it’s like China you may get throttled considerably and “raise flags”
I never had issues with SK but it’s been a minute. I doubt it will be an issue.
How do they detect it?
Are we talking commercial VPN like Nord or Proton? What about something like Tailscale to connect to your home network?
Sure, they could block based on your VPN provider, but they're probably also using Deep Packet Inspection .
The ELI5 verson: It's possible to just "watch" your traffic and notice that it's not the "normal" https traffic (which is the most common traffic) . This can be done by finger printing the request itself or just watching the amount of traffic. For example if you "visit" a website, but upload and download 3 megabytes of data and it takes 15 minutes to send/receive that data... well, that looks suspicious... and depending on the country, you may have some people knocking on your door.