How much I can depend on TOR to protect my identity, especially from outlook.com

Question

guys

I am using Tor browser from some time, few weeks maybe and I am still trying to determine the level of anonymity that the browser gives.

I am using the browser to advertise a service that I am offering in social networks. I create the accounts using outlook.com e-mail and since I am using Windows OS, I was wondering if outlook.com could get any information about my real identity when I am using their e-mail services. I am asking this because I have heard that if some company has a software installed on your computer, it can detect your MAC address. And what concerns me in particular is the fast that when I log into my outlook.com e-mail, it shows that I am active in Skype and Messenger. Since I never linked my skype account with the outlook.com account, they shouldn't have such kind of information right?

So my question is - is there any chance that Microsoft and Outlook.com could have any kind of information about my true identity, I mean about the fact who uses the particular @outloo.com e-mail address and such? Is there any way for them to disclosure my true identity if the police asks them to? Such kind of things.

Thanks in advance to anyone who would be kind enough to answer my question.

Best regards, Cairien

Answer 1

You say that you do not trust Microsoft and want to hide your identity from that company.

However, this is gapingly inconsistent with your action of using an operating system that consists of countless of megabytes of binary executable code produced by Microsoft.

Suppose that you use an operating system whose vendor you do not trust; you suspect that it might gather information about you and leak it.

A way to combat this is, firstly, not to enter any personal information into that computer or through that computer.

Secondly, treat it as a potentially harmful blackbox and firewall it properly: use your external router (not the internal firewalling features) to block that box from connecting to anything on the Internet. Make only a rew judicious holes in the firewall for any needed access, and only to specific IP or domain name destinations.

Do not enable any "automatic updates" (they shouldn't work anyway since they are blocked). Use alternative means to keep that OS up to date that do not involve "phoning home", such as using another computer to download service packs and transferring them to that computer.

If you in fact completely distrust the vendor of some device and its operating system, yet for some reason still want that on your network, you should use a two firewalls: it should go through a firewall to talk to other nodes on your local network, and to go outside. This way you have some protection against that untrusted device attacking our LAN, and from that device phoning home to relay information.

Answer 2

I doubt anyone on this site will be able to tell you exactly what sorts of information outlook.com is recording, or how precisely that information is being communicated to MS. Microsoft doesn't explain the full details of that in most cases.

What I can say is that Tor on its own may not be enough. In fact, if you are doing something questionable, it might not of much help at all. If Tor is comprised at an exit node, you will be in big trouble.

Also some agencies have some pretty nifty ways of tracking you down over tor http://www.cnet.com/news/nsa-tracks-google-ads-to-find-tor-users/

All in all, using Windows as an OS doesn't help your case. While explicit backdoors into Windows from Microsoft itself are denied by Microsoft, Windows has less than optimal security in the first place, and I would not be surprised if outlook.com was set up to communicate with your OS in ways that you do not like.

If I were you, I would switch to a security oriented operating system like Tails OS, and avoid using outlook.com if at all possible.There are operating systems, and e-mail services which better preserve your privacy.