How Secure Email Worksīoth methods use Public Key Cryptography to digitally sign, encrypt, and then decrypt your email. You probably know of this one in the form of OpenPGP. Another is PGP, which stands for Pretty Good Privacy. One of those is Secure/Multipurpose Internet Mail Extensions, or S/MIME, which is what Apple Mail uses. Groups came up with several standards to accomplish this. Basically, we needed to be able to digitally sign, encrypt, and then decrypt our emails. That quickly changed, and we needed to find ways to make our email communications more secure. Internet developers first standardized the Simple Mail Transfer Protocol, or SMTP, in 1982, when there was little concern for security. (Image Credit: Pete Linforth) An Abbreviated History of Secure Email There are several ways to secure email, so let’s look at how they differ. What’s better to secure email, Apple’s Mail app or a solution that uses OpenPGP, such as GPG Suite? Let’s take a look. I showed you recently how you can set up email encryption in Apple’s native Mail app, and that raises an interesting question. Every citizen of the Internet should know how to encrypt emails should the need arise.When you want to send secure email, you have plenty of choices. There’s little reason to make it easier for corporations and government entities to spy on you. While everyday communications might not require encryption, sensitive conversations could. Enter your passphrase to decrypt the email. Right-click on the encrypted text and choose “OpenPGP: Decrypt Selection” from the “Services” menu.Ĥ. Select the entire text of the encrypted email, including -BEGIN PGP MESSAGE- and -END PGP MESSAGE-.ģ. Copy the encrypted text into a plain text editor like TextEdit.Ģ. Decrypting Emailsĭecrypt emails outside Mail with OpenPGP’s context menu tools.ġ. Send the entire text block to the recipient. Choose the recipient from your keychain.ĥ. Right-click and choose “OpenPGP: Encrypt Selection” from the “Services” menu.Ĥ. Select everything, including the PGP key at the bottom of your email. Right-click and choose “OpenPGP: Sign Selection” from the “Services” menu.ģ. Write the text of your email in your email client or text editing window.Ģ. Composing and Encrypting Emailīefore you begin, make sure you have your recipient’s PGP key downloaded in GPG Keychain.ġ. You can turn off the other OpenGPG services to keep your context menu tidy. Scroll down to the “Text” section of the services menu, and look for the services prefixed by OpenPGP. Click on “Services” in the menu on the left.ģ. Open Keyboard in System Preferences and click the “Shortcuts” tab.Ģ. Encrypt the text of the email with GPG in a text editor, then send that encrypted block in your preferred email client. You can also use other applications to send an email. The check icon next to the lock indicates that you signed the email with your public key, verifying that it came from you and was not altered in transit. Click the lock icon to encrypt the email. Type in an email address that has a public key associated with it in GPG Keychain.ģ. Look for the green icon in the upper right.Ģ. Select the recipient’s most recent public key, and click the “Retrieve Key” button.ġ. Click “Lookup Key” in GPG Keychain or press Command + F to search by recipient name.Ĥ. Click the dropdown menu to select a keyserver.ģ. Click the “GPG Keychain” menu in the menubar and choose “Preferences.”Ģ. Search public keyservers for shared public keysġ. With a public key you can encrypt your email so that only the mathematically associated private key can decrypt it. Move your mouse around randomly to generate entropy for your random key pair generation.īefore you can send encrypted email to anyone, you’ll need a copy of their public key. Click “Generate Key” when you’re ready.Ĥ. You can use online tools to generate a random passphrase if you can’t think of a good one. Create a complex passphrase.You’ll type your passphrase to decrypt encrypted communication. Type in your name and email address associated with your email in your Mac’s Mail.app.ģ. You can also click the “New” icon in the toolbar.Ģ. The first time you open GPG Suite, you’ll be prompted to generate a key pair. Use your private key to “unlock” received emails. The public key is shared with people who want to contact you. Mount the DMG and double-click on the “Install” icon to install GPG Suite.Ī key pair includes a public and private key. It’s a reliable source, but you can see for yourself by reviewing the code on their GitHub page.Ģ. GPG Tools is a long-running open source project based on Pretty Good Privacy or PGP. Download GPG Suite from the GPG Tools website. They also can’t encrypt your subject line, so keep it generic. Email servers need those in the clear to route your message. Keep in mind that no PGP client can encrypt “To” or “From” addresses.
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