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Originally Posted by ManWithGloves
If you are looking for OPSEC, don't use Ubuntu. Use the Debian based Whonix.
This is the best way:
VPN > WHONIX VM > TOR > PROXY
VPN: Your ISP won't see you are using TOR, you will never become suspicious
Whonix Workstation: The VM helps you to isolate your work in a safe environment. the Whonix is focused on privacy and anonimity
TOR: You can connect to the TOR network thru the Whonix Gateway, this way you will be safe by the Onion router
Proxy: The websites you visit won't see you are using tor, so you won't be suspicious for them. For example Google won't show catcha all the time.
The Proxy can be avoided.
If you prefer Windows: try the FFOX VM. Connect with the Whonix Gateway.
It can be useful also for fingerprint spoofing, but nowadays their service is not running 100%
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don't forget to encrypt your entire system, you could even create a secret hidden operating system using veracrypt and have it dual boot with your everyday operating system. Look into distros such as QubesOS and SubgraphOS they're pure security based distros like whonix