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OpSec - A beginners Questions

zaderoni

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Good afternoon everyone, I am new here but may become a frequent contributor. Am new to a lot of things, but am eager to learn and would prefer any posts/threads I make to be for educational purposes...which means limit the bashing and keep things productive! This is how we learn.
In any case I wanted to discuss some opsec for darkweb and the Dos/Donts/and some ease of use.
First lets take an example of minimal opsec, then a more advanced. Curious on your thoughts on both.
Example 1 (The Basics)
Lets say Joe wants to produce an order from a home PC. He isn't super paranoid so his opsec is a bit lax, lets say the following.
Windows PC with PrivateVPN
Joe logs on to PC, turns on his P-VPN and sets it to Singapore. Loads up his TOR browser and orders some product using Bitcoin, his tumble is kept to a minimum, so its (Market transferred to Electrum, then transferred to his market). Does some PGP Encryption for the order.
Is this really that bad?
I see more people leaning towards what I personally think of as extreme
Tails USB
Laptop
Someone else internet
Bridge
TOR
Bitcoin market -> Electrum -> Transfer to Tails Electrum -> Tumbler service -> Market
Product order
Is all this a bit overboard?
I was also thinking a burner Virtual Box, for example
VM Ware
Whonix (I am still struggling to get this to work properly between workstation and gateway)
Maybe have a small drive created for storage of files
Bitcoin Market -> Electrum -> Market
Purchase products
Receive product
Delete the VM Box and Drive
Use Eraser to delete any remnants of data on HD
Curious on what level of Opsec is really needed versus how much is just paranoia and then people end up getting caught at the post office lol
 

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