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The only way to be sure that your email conversation is truly confidential between the conversing parties is to use end-to-end encryption technology.

Aside from that you would need to either:

• Trust your email service provider. Please see To find a reliable email provider and ensure that your recipient uses the same provider.
• Trust the provider of an encrypted messaging service (for example, that they have properly implemented algorithms and set-up a service to be resilient from any type of 3rd party interference).

Some suggestions for encrypted messaging services built as open-source software

• https://peerio.com - encrypted messaging and file sharing where you dont need to learn about GPG encryption. Required for all recipients. Cannot be used with regular email addresses.

You can always turn to a proprietary solution (e.g. http://www.symantec.com/desktop-email-encryption) that may intergrate nicely with your email client and remove some of the learning requirement from the process. We cannot recommend any commercial solutions, especially those who do not disclose their code for inspection. Keep in mind, your recipient may need to use the same software solution.