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Why do some people say that using Tor within my normal operating system will not be safe? What differentiates Windows and Tails in this regard?
I believe that running Windows together with a VM, VPN and Tor is safe. If that is not the case, what makes Tails superior?
From the networking perspective it doesn't make much difference whether you use Tails or Windows/Linux; Tor protects the source of the traffic equally.
From the OPSEC perspective Tails is better, because it lacks persistence, as explained in How Tails works:
Tails always starts from the same clean state and everything you do disappears automatically when you shut down Tails.
Without Tails, almost everything you do can leave traces on the computer:
Additionally, with Tor you should avoid standing out in a crowd. If you create something customized by yourself rather than using standard tools you might be vulnerable to browser fingerprinting. Whether using Tails or not, you should at least use the Tor browser and update it regularly.
The main "security" (I'd rather say anonymity ) difference between tails and Windows is in term of Hardware : Tails does not save anything on your HDD, everything is saved on RAM and when you shutdown your OS, you'll erase/recover your RAM's data. So, if someone gets your computer after you've shutdown it, it is supposed to be impossible to get any information.
As said before, in term of network it's supposed to be similar.
