Ok let me give you a small background of my problem. I am using a (very good) VPN service as I am trying to hide the fact that it is me (ip:....,name:....,etc) who is managing a particular website. I use VPN, sometimes tor, truecrypt etc, but my knowledge of these security tools is limited. Some time ago I did a couple of stupid things: like to speed up my connection I decided just to disconnect my vpn while browsing more specifically while using a yahoo email account. I did the same while browsing sites where I have a paid account. Now what I want to know: what are the realistic consequences of my behaviour for my anonimity status. I read in this forum that authenticating to social media destroys every bit of anonimity you ever had. Is this true, or is this just a worst-case scenario Would it not require a pre-established monitoring tool on the endpoint of my vpn, and a conscious decision of a monitoring human agent to follow up on these findings and ask for the network logs of these service providers. Is it not more likely that yes there are incriminating ip-records in databases, but as no one yet has any real interest in me nothing will be done with them?

I also sent pgp encrypted messages through yahoo. Am I now marked as being a suspicious character and how likely is it that from then on "they" will try to track me?

closed as primarily opinion-based by Jens Erat, RoraΖ, Polynomial, Stephane, CodesInChaos Jun 8 '15 at 17:12

Many good questions generate some degree of opinion based on expert experience, but answers to this question will tend to be almost entirely based on opinions, rather than facts, references, or specific expertise. If this question can be reworded to fit the rules in the help center, please edit the question.

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    Well I would say it depends upon what you were doing when you were not browsing via VPN. I hope you didn't try to hack someone who will come back searching for you or performed any illegal activities. Email services usually have a record of the IP address that accessed a particular account. Apart from that many services/servers in the internet keep logs too. – ρss Jun 8 '15 at 13:59
  • You're going to need to provide more details about what you were doing, who would be interested in your activities etc... My suspicion is that this site is too public for you to disclose enough information for us to help you. – Neil Smithline Jun 8 '15 at 15:30
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    Sorry Ross, you'll spend the rest of your life behind bars. – CodesInChaos Jun 8 '15 at 17:13

Consequences depend on, who do you want do prevent from tracking you:

  1. adversiters and small/poor site owners - sleep safe.

  2. big site owners, that can afford Big Data (eg. Yahoo) - they can time-correlate your visits, but rather for statistics, UX analysis etc., than personally.

  3. local Police or other local forces - they can possibly deanonymize you, but rather only in "hard" cases, like murder, rape etc.; it will take some time until they eventually do it.

  4. NSA, FBI, CSEC, GCHQ - you should assume, that they already deanonymized you. However AFAIK they are involved only in very serious cases, and it is unlikely, that NSA databases will be used for anything not involving terrorism, mass murders, homeland security etc.

So if you're not already arrested and you weren't interrogated by FBI, then you can assume, that they are not interested in you (as for your past activities only!).

AFAIK using PGP gives you 2 consequences:

  1. You are indeed marked as suspicious by XKeyScore.

  2. All PGP keys and messages obtained in any way by NSA gets recorded, so in case of private key leak they can be used against you even after X years.

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