Originally Posted by syncmaster913n
Could you elaborate a bit on why SSH over TOR is more anonymous
than SSH over nested VPNs?
With VPNs, records may be available that could deanonymize you. If your VPN provider(s) cooperate, and if there are logs, determined adversaries might work back to you. Even without cooperation from your VPN provider(s), traffic analysis might localize you.
With Tor, adversaries would need to compromise an elaborate system that's designed to resist compromise. Although Tor is by no means invulnerable, and is plainly labeled as experimental, it very likely offers stronger anonymity than VPNs. There are some long threads about Tor vs VPNs on Wilders, if you want more.