To your precise point:
How to Use a VPN and Tor together
https://proprivacy.com/vpn/guides/using-vpn-tor-together

Why using a VPN and Tor together can backfire on your privacy
VPNs and Tor both offer security, but using them together isn't always safer. Here's what you should know.
https://www.pcworld.com/article/2791638/why-you-should-not-use-a-vpn-together-with-the-tor-network.html

In general, for beginners:

A VPN routes your traffic through one server at a time. You can change it to suit location.
Most are encrypted, so your coffee shop traffic can't be easily hijacked and decrypted. (1)
Same for your ISP.

Tor "onion router" sends your encrypted traffic through a bunch of servers, with one exit server at a time.

I looked for an article NOT written by a VPN company. Most are, and are pitching their product.
This looks informative and neutral.

https://www.forbes.com/advisor/business/tor-vs-vpn/

The information at EFF is comprehensive, but a little hard to search through (because there is so much)
Recommended: (AWESOME)
Surveillance Self-Defense
https://ssd.eff.org/

Tor at eff:
https://tor.eff.org/

(1) an https connection should help, but I am not sure where MITM (man in the middle) attacks play in this.

Up until the last few years it was easier (to me) to find out this type of info. Now there are so many results from outlets I'm not familiar with and thus don't know are trustworthy, so I post in communities instead. I appreciate the links.

That using Tails with a VPN is one of the more secure methods. Tails is an open source OS that you load from a stick thus leaving no trace on your device. Tor is loaded from within Tails. That being said, the general consensus is that absolute anonymity is not possible (CIA, NSA) but other than that, you can be pretty close. There is some debate on whether you should do VPN first and then TOR or vice versa.

Never even heard of Tails. Will research. Much appreciated.

Yeah, I'm not talking CIA-level anonymity but just not easily swept up in whatever tools are being used to scour social media, for example.

But it's a complete operating system.

Check the details (pun not intended) here.
https://tails.net/

Lots of details.

Last edited Sun Sep 14, 2025, 11:34 PM - Edit history (1)

How securely you connect to anything, whatever you post is public unless you mark it private.
Can't do that here.

Other sites will let you limit visibility, and DU users have asked for post hiding, as there is for certain admin threads.

One "bug" with Signal and other secure messaging apps, is that when you share something, it's as secure as the other person's devices.

So, secret Signal messages were uncovered when recipients were asked or coerced into unlocking their devices.

So happy to be retired from the mad world of IT and security precautions, though I am OK sharing what I know and find, and using when necessary. I scan the tech blogs (that is, Hacker News, which is for "white hat" people. Mostly programmers and VC's)

I do try to be diligent about privacy settings. I didn't think about how the other person's settings could affect it.