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I want to send an email to another user with the contents encrypted. Do both of us use a VPN to have the email be fully private? Or is it enough for only one user to be on a VPN. If both, then do both have to use

  1. the same VPN service and
  2. the same login?
  • 6
    A VPN has nothing to do with the privacy of email contents. – forest Jan 28 at 3:33
  • I thot a vpn was an encrypted stream the acted somewhat like a private lan? no? – rlm1111 Jan 28 at 3:50
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    A VPN can protect from your ISP sniffing, but it does not encrypt email content. The email server and every computer connecting to it can still read the emails in plaintext. – forest Jan 28 at 3:50
2

By default email is like a postcard: anyone delivering it can read all the contents.

On the privacy for the connection (putting the card on an envelope):

  • The connection between mail user agent (client software) and email server should always be encrypted to protect your passwords, and a webmail must be used over HTTPS. In these circumstances, if both the sender and the recipient are on the same server, the connection is secure. A VPN adds nothing to this.

  • Connections between mail servers can be encrypted, too. As of Jan 2019, 91 % of mail to and from Gmail is encrypted in transit. However, using TLS is negotiated during the SMTP connection and doesn't have strong CA infrastructure like HTTPS: it's currently very vulnerable to man-in-the-middle attacks. DANE TLSA (RFC 6698) records on DNSSEC signed zones can solve this, but the implementation is slow.

  • A typical user can't really estimate the level of transit security: it's still best to assume it's nothing more than a postcard.

  • The administrators of the email server can read the content. It's illegal and unlikely, but possible.

For full privacy encrypt the content. A VPN doesn't encrypt the contents, just the connection. Start by reading some tutorials about Pretty Good Privacy (PGP).

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VPN is only the encrypted tunnel that your traffic/email travels through, but it doesn’t encrypt contents of your email. You’d want to research a bit into PGP or s/MIME, as those deal with the actual encryption of your email contents.

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A VPN is just like a tunnel between your city to the other city in which you want to deliver the message. Let's assume that you are a message carrier, and you are having a text to deliver. For security, you'll use a tunnel, your VPN is in short tunnel will protect/hide you to the people who are going to steal information through you.

But encryption is something like other thing. We can say that encryption is something you know the message in some code-word. You only know the code of the message and you know the person you are going to deliver the message. The writer knows the encryption technique and decryption both. Here encryption means how you generated the code of the message you are going to deliver. Decryption means how to convert code-word to the original message.

What will happen if someone steals code-word from you? Nothing. Your code-word will not be useful unless he knows the decryption technique. It is called security.

One thing more, I don't think any mail services like Gmail, tell anybody how they encrypt and decrypt. In general, nobody knows how the generated code form your given data, and your mail domain holder knows both techniques. When you compose an email it is encrypted for security reasons by the mail domain and then it is sent. Then it is decoded. So it is not necessary for both of you to use the same VPN.

The other thing if VPN encrypts your data, that means he also knows how to decrypt it, and they will give the data to your mail holder according mail encryption. In this case, double encryption will be used first for mail domain and second for VPN.

  • 1
    This is very difficult to understand. – schroeder Jan 28 at 12:35
  • all you need is to place yourself as message carrier and sometime you'll need to consider yourself mail domain holder.When i was talking about tunnel and message carrier you should think you are the one who is carrying message , when I'm talking about domain you should think yourself as an ordinary person also and then you need to be domain holder also – J.Doe Jan 28 at 13:33
  • it's basically a wide thing to clear you everything I need to type much that could be difficult I'm just giving you the rough idea – J.Doe Jan 28 at 13:34
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    "All you need is Faith, Trust and a little Pixie Dust." You don't have to explain everything: just the facts that answers the question. Now, encryption is like this answer: it must be decrypted first. – Esa Jokinen Jan 28 at 18:12
  • There are several factual errors in your answer. Knowing the encryption technique does not matter. The whole point for modern encryption is that you can know the technique and the message is still secured. VPNs are not a tunnel between you and the email recipient. VPNs are not even a tunnel between you and Gmail. VPNs are a tunnel between you and the VPN server, wherever that is, then the traffic goes unencrypted from there. – schroeder Jan 28 at 20:08

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