I want to explore the dark web, but want to do so safely. I want to make sure I have everything in order before doing so

VPN
1

So I only have a desktop PC at home. Its just your standard gaming rig with windows. I do have Nord VPN. So…

​

  1. Start up a VM using VMWare

  2. Start up my VPN so my ISP doesn’t know i’m using TOR

  3. Start up Tails OS

  4. Enjoy???

​

​

I don’t plan on saving anything, downloading anything etc…just wanna see what I can stumble upon I guess. Would I need Whonix?

2

I want to explore the dark web,

.

I don’t plan on saving anything, downloading anything etc…just wanna see what I can stumble upon I guess

Then Tor Browser on Windows is fine. You’re not going to get into trouble. You’ve been mislead about the reality of “the deep web.” Skip all that VPN + VM + Tails business. It doesn’t matter for you. It’s unnecessary overhead that you don’t need and may make things worse instead of better.

3

I know it hasn’t been said and is rarely touched upon these days, but if my information still holds true. A vpn with Tor kind of defeats the purpose. By using an exit relay you are mostly anonymous due to all traffic leaving the exit node. Using a vpn makes you stick out as you’re using Tor over a vpn which is a set IP for your vpn specifically. Perhaps things are changing and vpn won’t make a difference but swim with the crowd on this one and let all traffic flow through the Tor exit node.

4

Start up my VPN so my ISP doesn’t know i’m using TOR

Tor Project documentation: “Tor is not illegal anywhere in the world, so using Tor by itself is fine.”

ISPs in many countries, including most liberal democracies, have Tor-friendly policies. For example, in the United States — Comcast Corporate Public Policy | Setting the Record Straight on Tor: We have no policy against Tor, or any other browser or software…Our customers can use Tor at any time, as I have myself. I’m sure many of them are using it right now. — Jason Livingood, Comcast Corporation, Sep 15, 2014.

Tor Blog - Tor at the Heart: Bridges and Pluggable Transports: Pluggable transports disguise the Tor protocol by making it look like something else—for example like HTTP or completely random.

5

For someone just curious, unless you are intending to look at illegal images, or commit crimes / buy something from darkweb markets Tor Browser on Windows is fine. You only need Tor Tails or Qubes in more extreme situations where you are either breaking the law or being exposed risks your real life physical safety.

6

The best thing you can do is not to go if you’re worried about safety

7
  1. Use Qubes-OS. It does give you more features and increase productivity. Unless you want Windows based OS.
  2. There are a lot of good third party VPN provider outside
  3. Qubes-OS is far better for security than Tails OS. Also you can run Tails OS in Qubes-OS
  4. VPN through Tor is another good option but as you said you didn’t want ISP to know that you’re using tor. In that case I2P could be good option? Or how about VPN cascading?
8

VPN+Tor is more then enough. VM and Tails OS is an overkill. Unless you are going to murder someone. Then yeah.

9

VPN and VM are perfect. you better use Parrot Os rather then Tails. It has an anonimity mode and is a full pentest OS that will give you better protection.

​

Use it as live.

​

first rule is NEVER DOWNLOAD ANYTHING.

you never know what kind of payload may be hidden in a .pdf of .png file.

10

This is the correct answer if OP just wants to check things out. All the other stuff is overkill.

11

I appreciate it, thank you!!!

​

Quick question though. Why, or how, would using a VM/Tails make things worse? Not trying to be a smart ass or anything, I genuinely want to know.

12

whatd do you mean “ then tor on windows is fine” is there another way to access it?

13

Thanks for the advice!

14

Don’t plan on any of that. Just mostly curious for the alleged “shock value.”

15

In what sense is Qubes-OS more secure than tails?

16

Qubes sounds good, but I just don’t feel like getting another HDD or partitioning part of one of my HDDs. I guess I could install it on a VM if I go that route, but others pointed out might be Overkill.

17

Whelp, certainly don’t plan on that lol. Ty

18

so first off what ever your doing Tor on MS Windows is safer than Firefox on MS Windows and saver than Firefox over a vpn on MS Windows.

The VM is still a window on the loading on the host (MS Windows) that can still see the window. As can another propriety program VMWare.

Tail, if you feel the need to use it, should be loaded as the base OS. (i.e. shut the PC down and start-up with Tails).

The VPN will slow your connection, but possibly as lightly to talk to your government as your ISP.

19

If you are looking for something that will shock you, you’ll likely be disappointed.

20

Base of my knowledge, Qubes-OS is based on Xen which is virtualization platform. Individual apps are running each VMs thus preventing security compromise on OS level along with linux sandbox feature. I haven’t used Tails before but it isn’t native environment for VMs and maybe not secure as Qubes-OS. It’s just relative reasons.