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What is the easiest, most secure way for me to send a one-time email to my stalker without him learning my general physical location from my IP? Can I do this by installing the Tor Browser and then using that to go through something like guerillamail? Will that mask my IP/physical location? I don't want to hear back from him. He just needs to be given some information. I'd rather use a disposable email if at all possible.

Believe me, he will sue an email provider to get my location if he can. If he knows the city/state, it's over. I don't have the money to run again should he find me. I'm not a hacker type, but I can follow directions step-by-step if there is a good guide somewhere. I'm using a Mac. Thank you.

EDIT

I saw that someone flagged my question as a duplicate and went to read what was posted under the other person's question. I appreciate the help, and please accept my apologies for saying so, but I'm not seeing a cohesive, easy-to-execute solution under the duplicate that fits what I'm looking for. It sounds like there's some disagreement on what really works, plus the most detailed answer went way over my head.

Someone suggested going to a local public wifi and using that, the library or a coffee shop, in addition to using TOR, squirrel mail, etc., but my stalker would still be able to figure out the city and state where I live from the public wifi's IP. If I had a car and the money to drive several hundred miles to use a public wifi that wasn't in my state, I would be on the road right now and none of this would be necessary. No need to hide the IP. If he believed I was in that other state, fantastic. Nor, do I need encryption. I couldn't care less who might see the email. My stalker doesn't need to verify the email was from me. He'll know. And the last thing I want to do is exchange correspondence with him. All I needed was a way to safely hide my location when sending him a single, one-way email. A method where him suing the email provider to get my IP would be difficult.

What I have learned from these extensive and thoughtful answers is that it's almost impossible to hide your location, and only someone with a specific skill set should attempt it. Which leaves me out. Thank you to whomever posted the link about TOR/Guerilla Mail. Whew, you saved me there. I was just about to go that route. Bottom line, decided it's better to take the consequences of not sending the email in the first place, than risk being found.

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Since you found the other answers unsatisfying here is both a tl;dr and a longread for you.

Step 1: Install Tails by following the step by step guide here.

Step 2: Create an email account with any email provider who allows signing up over tor and provides webmail access. The provider must either not ask for or not verify personally identifying information. If the latter, provide false information.

Step 3: Send your email from webmail.

Since the browser doesn't report your local IP to the webmail it can only see the Tor IP neither they, nor the recipient will have knowledge of your true location.

However, anonymity and "hiding your IP" are different things, sometimes it's mistakenly assumed that the latter ensures the former but this isn't true.

Things to consider:

  1. The Greenpeace fallacy, or "I solemnly swear that I'm up to no good".

    • Greenpeace used to use PGP for their emails but they decided that they would only use PGP for their emails when they were planning something risky/big/important. This acts as a signal to anyone watching. Who is emailing who with encrypted emails and when would reveal large parts of their plan to any observer. Similarly, if you use Tor once and the only time you use Tor is at the same time as the email was sent from Tor, that's going to look suspicious
  2. Acting locally.

    • When people do something naughty anonymously they often make the mistake of trying to influence something local, often personal. This means that no matter how well obfuscated your network connection is, the list of people local to the issue who are Tor users is quite small. It will make you (and any other local Tor users) look very suspicious indeed. If your "stalker" knows who you are then your email will likely reveal your identity even if you never explicitly state it and consequently, your identity will almost certainly reveal where you are.
  3. Pattern recognition.

    • Acting anonymously with a single act with no long term identity is workable. In reality however, most people don't want anonymity for most things that they do socially. Instead they wish to create a pseudonymous identity, this is an identity that is kept long-term but is never linked to their real identity, but that people might recognise them by. Remaining pseudonymous with a long-term identity while also acting with your "real" identity is a lot harder to do. Patterns between activity and no activity, patterns in stylometry and patterns in behaviour eventually build a link and normally most people under pressure will make a catastrophic mistake before that even happens. Do not repeatedly and predictably return to the same watering holes, lest they become traps.
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A service such as https://posteo.de would allow you to create an anonymous email account, that is completely disconnected from any real world information. Posteo strip any IP addresses from the header, so he will not be able to find your location. Here is their privacy page.

This should be reassuring in terms of him trying the legal route to get access to your information:

With Posteo, you sign up without having to enter any personal information. We abstain in general from saving personal information. This prevents the pile-up of data and constitutes acting in line with the principles of data economy. We give you back sovereignty over your personal information and increase your right to informational self-determination.

Under German law (TKG §111) email service providers do not have to collect user information if it is not necessary (e.g. for billing purposes). Posteo makes use of this regulation."

I hope this helps. I know that this isn't to do with tor but this should work if you want to create an email address anonymously.

  • This is misleading, see the comments made on the question this is marked as a duplicate of. Also please don't shill specific services with privacy-by-policy promises. Those privacy-by-policy promises do not hold in the real world. – cacahuatl May 23 '16 at 0:58
  • Thank you, Steven. :) Extremely helpful. I'll go check it out. Just looking for the simplest, most expeditious method I'm least likely to mess up. – missing876 May 23 '16 at 1:15
  • Okay now confused by canonizing ironize. The service doesn't do what it says? – missing876 May 23 '16 at 1:17
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    The service provider alone cannot protect you no matter how many fancy privacy policies and promises they make (yes, even lavabit did it wrong). You should operate such that even if they didn't protect you, you would be safe. IE, using webmail from tor browser or from tails. The provider doesn't matter as long as they don't require personally identifying information when you sign up. Assuming all you want to do is hide your IP address, this is sufficient. – cacahuatl May 23 '16 at 2:12

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