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I've seen articles stating the best practice for connecting to Tor is through a VPN, however where this setup fails is at hiding your traffic from a malicious Tor exit-node. Because the traffic goes through the VPN, and then to the Tor network, exit nodes can still watch your traffic unencrypted. Also, if the VPN provider is logging traffic, then using a VPN won't be too much different from just using your ISP. Layout would be: Computer --> Encrypt w/ VPN --> Tor Entry --> Tor Exit --> Decrypt w/ VPN > Destination.

My current setup is using the Tor Network as a SOCKS Proxy then connecting to Tor.
Computer --> Tor Socks Proxy --> Tor Entry --> Tor Exit. I am sure my connection is not encrypted because SOCKS similar to HTTP does not form an encrypted connection. So my question would to be what is the best method of ensuring my Mac is getting full anonymity while safely connecting to Tor.

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Tor, by default, only uses SOCKS5 on the local loopback interface.

This is a virtual interface that only your own computer can see. Anyone who could see your localhost Tor traffic could also see your VPN traffic before it is encrypted, so the VPN adds no value.

As you've also summised, using Tor to a VPN then links all your Tor activity back to the VPN account, and your identity.

At this point your VPN provider is in a position to act exactly like a bad exit node except worse because it also can link it back to an identity/account and target or track your activity over time to profile you, which an Exit node wouldn't be able to do through normal Tor Browser operations.

The Tor client, when sending traffic out to the internet into the Tor network is always sending the traffic you put into the SOCKS proxy through a Tor circuit, so it is already encrypted.

The best protection is to use transport layer security for traffic that is going over the Tor network, e.g. by using TLS/SSL.

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tl;dr:

What is the best practice for having an encrypted connection while connected to Tor?

all connections to and through Tor-network are encrypted! the only critical leg is the way from the exit node (the point where your data leaves the Tor-network) to the destination...
simply make sure to use a SSL/TLS-encrypted connection (for webpages via https) to the destination.

further reading at the section "Use HTTPS versions of websites".


[...] articles stating the best practice for connecting to Tor is through a VPN

NO, it is not! - they are either not knowing what they are talking about or want to sell you something. either way, hands off!!!

[...] exit nodes can still watch your traffic unencrypted.

not necessarily, it depends! - as already stated: use encrypted protocols and you are fine.
here is a nice interactive website to find out who knows what, depending on the setup: https://www.eff.org/pages/tor-and-https

Also, if the VPN provider is logging traffic, then using a VPN won't be too much different from just using your ISP.

exactly! it is just an other (resp. another) man in the middle.

So my question would to be what is the best method of ensuring my Mac is getting full anonymity while safely connecting to Tor.

a VPN can only help to hide from your ISP the fact that you are using Tor; BUT i don't advise this setup, because a VPN can counteract the Tor-usage and harm resp. destroy your privacy/anonymity elsewhere.

if you want to hide the fact that you are using Tor or unable to connect because of censorship use bridges instead!


once more back to the VPN-topic in general:
a VPN has nothing to do with anonymity! - it just encrypts your traffic from your device to the VPN-server (which is just another man-in-the-middle); and from there it is redirected "unencrypted" (resp. as much/little encrypted as it were without a VPN) to the destination. - therefore it may only be an improvement, if you strongly distrust your ISP, hotspot, etc. (but then you still have to trust the VPN-provider!).

additional some important things regarding Tor and VPN: Is Tor like a VPN?

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