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Would I be "somewhat anonymous" if I purchased bitcoin using my real bank account, used that bitcoin to purchase a VPN-service that I can trust does not keep any logs, and use that VPN-service through TOR?

I may want to write about somewhat controversial subjects on the internet and watch some copyrighted streams of TV-shows. So by "somewhat anonymous" I don't mean the most hardcore security agencies, but private people, enforcers of copyright law etc.

Anything I should think about, anything I've gotten wrong? Tips?

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    This question is pretty broad. Can you narrow down your question a little? – schroeder Dec 22 '15 at 21:34
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    Awesome and interesting topic for a long blog post, but by far to broad for SE. And yep, you have that VPN thing wrong. – Sebb Dec 22 '15 at 23:13
  • @Sebb There's quite a lot of blog-length answers on this site that are incredible, so I don't think that really applies. – user72066 Dec 23 '15 at 0:02
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    @SourLolita Yep, there are awesome long answer here and I do like them. However, there are so many possibilities and things to look out for that a good writeup which includes at least most most of the traps will take several pages - a lot longer than all answers I have seen. – Sebb Dec 23 '15 at 5:42
  • @Sebb Ah, I see your point now. – user72066 Dec 23 '15 at 7:58
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If you buy bitcoins with your real name attached to them, you wont be anonymous. Bitcoin is not anonymous by itself (http://www.bitcoinisnotanonymous.com/), and using it with your real name makes thinks only worse from the anonymity perspective.

Also I would not trust any vpn provider. But I if you really want you have it backward. Run tor through the VPN, not the other way around. At worst, vpn privider will monitor your encrypted tor traffic only.

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The problem is the transactions with bitcoins are publicly logged so anyone can see the bitcoin transaction.

There is a page from bitcoin wiki on how to keep your bitcoin anonymous titled Bitcoin Wiki - Anonymity. There is a section "Staying Anonymous", that will explain you how to transfer the coins between many accounts from different eWallet providers.

So to your first question

Would I be "somewhat anonymous" if I purchased bitcoin using my real bank account, used that bitcoin to purchase a VPN-service that I can trust does not keep any logs, and use that VPN-service through TOR?

Its no, first of all buy the bitcoin with cash and in small quotes and you still need to transfer your coins through several wallets - instead of tor use tails , its a whole amnesic and anonymity distro instead of just a anonymity browser. Use proxychains and a vpn as well to create the ewallets and transactions.

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Bitcoin keeps an active ledger. When you buy btc with a bank account via a provider like coinbase they log that transaction and transfer bitcoins to your address then you buy vpn service with the bitcoins and the bitcoin ledger logs the transaction. I would use a service like LocalBitcoins to trade gift cards or cash for btc...that is more anonymous

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