Update: Here’s a great primer on anonymous emails and private email services that are available in 2018.
One of the most private email communication systems consists in using Tor or a VPN to connect to a free webmail service and encrypt the messages yourself with PGP, this method gives you privacy and anonymity. Thunderbird+Enigmail, or GPG4Win can do that and it won’t cost you a cent, the problem is the time and learning curbe it takes to do this.
ProtonMail: Company keeps minimum logs and can not read your data as the inbox is encrypted. Servers are based in Switzerland. Communicating with other Protonmail users is end to end encrypted, and emailing other email providers is done in plain text, to make the best of this service your friends should ideally be using too. the company itself can’t read your data.
Tutanota: Email privacy service based in Germany, messages are encrypted in your browser and nobody can access the encryption keys, Tutanota staff has no decryption keys, they keep no login IPs and have no way to identify customers or decrypt data. They also publish transparency reports showing how many court orders they had and what it was done about it, like, handing over encrypted data.
Unseen.is: Iceland based privacy platform providing encrypted video calls, chat and email service. You can have a free limited account that will never expire and use it to send email with your computer IP hidden. The same company also offers private hosting in Iceland.
VFEmail: With support for PGP encrypted webmail using the interface and anonymous sign up using Tor, this service has a Tor hidden node from where you can access your account. Metadata is scrubbed from emails and your computer IP removed from the headers.
ScryptMail: End to end encryption with other ScryptMail users and no metadata stored by the servers, your own inbox is encrypted with AES256. Code is available for auditing, it can be checked for backdoors or vulnerabilities. Currently the service is in beta and free.
InvMail: Hong Kong based secure email provider with servers in Switzerland, using open source 4096 bit end-to-end encryption and zero knowledge architecture where the company is unable to access the data. Good looking easy to use webmail interface that automatically encrypts your messages with PGP. Paid accounts give you access to secure video calls on top of email services.
Mailfence: Email service hosted in Belgium that supports sending OpenPGP encrypted messages and two factor authentication. Seamless keystore integration. All encryption happens in the browser. Service includes a calendar and cloud document storage with paid for accounts giving you access to Android and iPhone apps to access your email using a portable device.
Safe-mail: Emails in between Safe-mail users are always encrypted, when sending messages to an external address a digital certificate can be used for encryption after importing it to Safe-mail or use a dropbox, they call it “Safebox“, where the other end is sent a link to a password protected page to retrieve the message. The company is based in Israel.
Hushmail: Offering automatic PGP encryption in between Hushmail users, it eliminates the sender computer IP from the headers, email can be accessed with a mobile device, compatible with the iPhone. If you don’t log into your free Hushmail account for three weeks your account will be automatically closed. The company headquarters are located in Canada.
EasyCrypt: An addon that works with the email service of your choice and it will strip metadata and encrypt messages even if your email provider does not support it. EasyCrypt sits in the middle of in between your email provider and the sender to encrypt communications, it also gives you an anonymous email address that redirects to your main email inbox and can not be linked to you.
NOTICE: List only includes services with free option. If you are willing to pay for a privacy email service other companies you should look at are Posteo (Germany), Countermail (Sweden), StartMail (Netherlands) and AnonymousSpeech (Asia).
Webmail services hiding your IP
The following email services do not encrypt your messages but hide your computer IP in the headers. I tested all of them and the sender’s IP is replaced with a neutral IANA (Internet Assigned Numbers Authority) private IP address, a range of IP addresses not linked to any country or person reserved for use in private networks, the only way to find out who sent the email is to contact the company and ask them.
Yandex: Russian email provider offering Email accounts in multiple languages, with huge storage space (10GB), eye candy interface of interchangeable themes, spam and virus filter and free storage for files and documents. Yandex strips your email from the headers but this is not a privacy service they keep internal logs of the real IP in case of abuse.
Zoho Mail: Easy to integrate with their online office apps to work with documents, there are no advertisements whatsoever and your computer IP is not present in email messages. Company based in the USA.
NOTE: Some email services will only strip your computer IP from the headers for webmail and include the computer IP in messages sent using SMTP.