That requires someone who has the ability to monitor all your traffic - ie the government, your ISP, or a hacker who has infiltrated one of those two. In this

That requires someone who has the ability to monitor all your traffic - ie the government, your ISP, or a hacker who has infiltrated one of those two. In this scenario it's a lot more work trying to map out your infrastructure than to try performing a MITM connection against some of your outbound traffic.