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So first, I know that VPN isn't exactly useful for anonymity. Did my homework about TOR and Tails.

However, I still want to use VPN, NordVPN to be precise. I want to avoid causing a paper trail through PayPal payment, and they accept Monero.

The Monero protocol itself seems to be pretty good. However, I also learnt that my privacy is just as hard as the weakest part of it. So I guess using Monero on the one hand, while on the other hand associating my VPN account to my regular mail address and not using TOR or the like to establish the VPN account wont help my privacy/anonymity much.

So, how can I maximize anonymity in this use-case? What should I do? Use tails for establishing the VPN account + trashmail? What else?

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Great question. What you are referrer to is known as OpSec or Operational Security which looks at multiple steps that need to be taken from the OSI model right down to the social and privacy consideration that could allow for attribution.

To maximise anonymity you will need to have a layered approach. This can consist of multiple different layers including but not limited:

  • Using Tails OS
  • Using a network off your own
  • Ensuring no link back to any personal accounts
  • Using disposable + trusted email accounts (Protonmail is okay)
  • Proxychains
  • Using a Monero Mixer (debate exist on whether a mixer adds or detracts from privacy)
  • Planning your process and looking for holes
  • Using bulletproof virtual machine services.

You can be as paranoid or liberal as you need with your OpSec. No need to break out the pigeon carriers just yet. The above ideas are not exhaustive, and novel combinations that cover each area needed are best.

For some good resources, please look at:

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