At DefCon 26 (25?) I attended two presentations that scared me:

1. there was a presentation about several admins in a hostile country who had been arrested because someone from Harvard pinged a server they ran as part of IPv4 measurement. The suggestion was to avoid measuring countries with strong censorship laws to prevent accidental imprisonment of innocent IT.

2. similar presentation about ToR project struggling to find fresh egress/ingress addresses. Authoritarian countries were making lists of any IP addresses that were known ToR IPs and prosecuting/imprisoning users associated with them as a result of traffic on those addresses.

I would be extremely careful trying to bypass authoritarian restrictions unless I was 110% confident what I was doing.