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enter image description hereMy goal is to get a clear sense of what is required to maintain anonymity. In a sense I'm mapping the flow of traffic in my head and trying to understand how certain traffic might interact in ways that aren't obvious. This is to say nothing for topics such as statistical analysis and analyzing totally disparate traffic streams.

For example, I've seen a number of people answer questions about Tor Browser and P2P and I want to know if I've correctly identified erroneous thinking. Here's what I've understood:

  1. Q: Where does encryption and connection begin? Your ISP is your ISP. Unless your connection begins elsewhere then that is the point of concern. Tor connection runs encrypted through your ISP. Using other programs in conjunction should generally not affect anonymity of Tor Browser. Basically all the Tor traffic is anonymous. The traffic from another browser or program may be unencrypted. Encryption has to begin on the system you are using. So there are several handshakes between different relays. What does my ISP see?

My first concern here is that when I use Test Tor Network settings (about:tor), I do get various IPs that are not assigned by my provider. However, after entering several urls directly, with Google as search provider, I was directed to a captcha at Google asking to identify as a human, showing my IP. At first I thought that it was my actual IP but I realized it was various changing IPs including IPv4 and v6 (Onion menu).

I ignored them and I can go to google.com search page with TLS 1.2, but once I enter a search query, whether from this page or url bar, I am directed to either the captcha, or if I ignored the captcha, then I get

Our systems have detected unusual traffic from your computer network. Please try your request again later. Why did this happen? (link)

I'm not sure if I should keep answering captchas identifying my address to Google, or if this is unnecessarily paranoid because I'm just letting Google know that it is legit traffic.

  1. My connection with my ISP isn't private. For that would I have to configure a VPN directly from my cable modem, meaning all my headers would look like a connection from me to VPN and that's it? Or what would this mean?

    1. As mentioned any program outside Tor Browser is operating normally. A lot of people have asked about torrents. This would run from the client and is not private. But I understand PHE (protocol header encryption) options are available for different clients.

    2. How are layers added to my anonymity? 1. I'm on my computer 2. using Tor Browser 3. insert VPN 4. What if My VPN is at 2 and Tor is at 3, what does my ISP see?

    3. I created a mail account I use only with Tor. All accounts I use are separate from those I use on other browsers. Although I use a password mgmt pluggin. I think I should also avoid logging in from Tor with the same account.

    4. What are some ways to analyze my traffic and remain anonymous while doing so?

Realized there is a lot I don't understand. If anyone could deliver answers in an ordered list to paint a picture of how this works that would be great. I will continue reading documentation.

Also links are appreciated.

closed as too broad by Jens Kubieziel Jun 28 '17 at 19:35

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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    Firstly, you should be asking one question per question. Secondly, most, if not all, of these questions have been answered elsewhere. – cacahuatl Jun 28 '17 at 1:45