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I have a vpn, if I connect it and create an email account while connected to the vpn, and then send the email to the desired recipient, what other levels of protection/anonymity am I missing? I use PIA (Private Internet Access). I have the kill switch on as well so if the VPN disconnects, it will kill my internet access. Also, what is the difference in this case between using Tor and the vpn? If I use Tor then if I send an email to an outlook or gmail account then would it go to their spam mail? I want to send an email from an outlook or gmail account. And can I access gmail or outlook through Tor? I want to know to what extent my VPN will help me from having my IP address traced back.

  • I know this is old, but I just want to mention that VPNs are not anonymity services and were never meant to be used for anonymity. – Steve Jun 24 '18 at 14:32
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I have a vpn, if I connect it and create an email account while connected to the vpn, and then send the email to the desired recipient, what other levels of protection/anonymity am I missing?

If you create and use the email account through an anonymizing service (your VPN) and use the service correctly, there is no straightforward way to de-anonymize you. Of course, the usual side channels apply. Your ISP might correlate the time of your VPN usage, someone might recognize your writing style, your browser can be fingerprinted, etc.

If you use Google Chrome through a VPN with GMail, they might also employ additional means to be able to exactly identify your browser instance and could theoretically correlate that with a point in time where you use the same Chrome instance without a VPN. In contrast to that, the Tor browser developers went to great length to prevent various ways of fingerprinting.

If I use Tor then if I send an email to an outlook or gmail account then would it go to their spam mail?

No. If you use a GMail account through Tor and send an email to an Outlook account, that's a connection between Microsoft's and Google's mail servers. For the mail delivery between the providers it doesn't matter how you connected to GMail in the first place.

And can I access gmail or outlook through Tor?

Generally, yes. But GMail and Outlook might employ anti-spam measures to cope with fake accounts and hence might block some Tor exit nodes or VPN servers. You'd have to try out for yourself.

I want to know to what extent my VPN will help me from having my IP address traced back.

That's too broad to answer in a single post. We have plenty of questions on VPN security here that you might want to have a look at. Also see: Differences between using Tor browser and VPN

  • Thanks! What does it mean that my browser can be fingerprinted? How can I prevent that and what is a browser instance? – user8358234 Aug 2 '17 at 16:43
  • Browser fingerprinting refers to ways to identify your browser. Even if you remove cookies, cache files, etc. there are ways to uniquely identify your browser. If a website does that once during your VPN usage and once without, they might still conclude that it was you. By "browser instance" I simply mean your exact browser installation. – Arminius Aug 2 '17 at 16:51
  • So can if I uninstall chrome and the reinstall it with my vpn and only use my vpn, does that change my browser instance? Also you said this is if I access gmail through google chrome, what if I access outlook via google chrome? does that change anything? – user8358234 Aug 2 '17 at 16:53
  • Reinstalling probably won't solve it, because fingerprinting includes details of your machine. That said, I'm no expert on means of fingerprinting, so I can't help you too much here. I was mentioning Chrome + GMail in particular because of the tight integration of Google services into the browser. Anyway, for everyday browsing, you might very well be fine with an ordinary browser through a VPN. If you want to get more in-depth you might want to ask specific single questions, and experts here will be happy to go into detail. – Arminius Aug 2 '17 at 17:02

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