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How to enable IMAP encryption in Apple Mail
Last modified on 23 May 2018 02:14 AM

To set up PGP Encryption in Apple Mail, make sure to first set up StartMail in Apple Mail, and to set up PGP encryption in StartMail. 

  • To set up StartMail in Apple mail, please click here.
  • To set up PGP encryption in StartMail, click here.


1.Download and install GPG Suite

  1. Download and install GPG Suite on your desktop or laptop (available for macOS 10.9 and newer).  If you're experiencing trouble installing GPG Suite, please consult their Knowlege Base here.
  2. Upon installation, GPG Suite may launch automatically and you might see a GPG Keychain Access window. If this happens, please click  Cancel.

2. Export and import your StartMail key pair

  1. Sign in to your https://StartMail.com account in a web browser on your desktop or laptop.
  2. Navigate to Settings > Mail encryption.





  3. Ensure that the box next to Use advanced options: is checked (This enables the selection of advanced PGP options).



  4. Find Export my own key pair: and click Export key pair.



  5. Enter your PGP passphrase when prompted and select Continue. (This is the same PGP passphrase you have set up to read and send encrypted emails, and it is not the password you use to enter your StartMail account.)



  6. GPG Keychain will signal that "One or more keys were detected in your clipboard", click Import when asked if you would like to import the key(s). (Please see notes below if GPG Keychain does not automatically detect the copied text).



3. Import public keys of recipients

In order to send and receive PGP encrypted messages in Mail, you will need to import the public keys of each individual recipient.

  1. To import your contacts’ public keys, log in to StartMail.com on the Web and go to Settings > Mail encryption.
  2. Next to PGP Keyring: find the email address of the recipient whose keyring you wish to export, and click export.



  3. In the Copy the text that begins with -----BEGIN PGP PUBLIC KEY BLOCK----- and ends with -----END PGP PUBLIC KEY BLOCK-----




  4. GPG Keychain will signal that "One or more keys were detected in your clipboard", click Import when asked if you would like to import the key(s). (Please see notes below if GPG Keychain does not automatically detect the text).



4. Send and reading an encrypted email

  1. Open Apple Mail.
  2. Begin a new email and select your StartMail address in the From: field.
  3. GPG Suite adds a Lock icon to the mail composer window, and it will be enabled when you select an email account for which a public key exists in the GPG Keychain Access app. Click the Lock icon, and your email will be encrypted. (If you cannot click the Lock icon, it means that you have not yet added the recipients public key. You can do this by following the previous step (4. Import public keys of recipient)).

     

  4. You can now send the email as normal.
  5. You can read an encrypted email by simply opening it in your Mail inbox. When prompted for your passphrase, please enter the passphrase you have set up to read encrypted emails.


NOTES:
- If GPG Keychain does not automatically detect your copied text, you will have to add it manually. To do this, you will need to use a text editor such as TextEdit.

  1. Open TextEdit, and paste the entire copied text (starting with -----BEGIN PGP PUBLIC KEY BLOCK----- and ending with -----END PGP PUBLIC KEY BLOCK----- ) into a new file.
  2. Save the file to disk with an .asc extension (ASCII), by selecting File > Save.
  3. You will have to manually add .asc to the end of your file's title, if this is not done automatically, and ensure that Plain Text Encoding: is set to Western (ASCII). (Note: If you do not see the ASCII option when saving your text file, please make sure it is enabled in TextEdit, by going to TextEdit > Preferences. Select the Open and Save option at the top, make sure the Add ".txt" extension to plain text files is not selected. Under Plain Text File Encoding, open the Saving Files: drop-down menu and select Western (ASCII). Make sure to select this option when saving your TextEdit file.)



  4. In GPG Keychain, click Import and select the .asc file you have created in the previous step.



  5. For privacy reasons, please make sure to delete the private key files from your computer as soon as you have imported your keys into GPG Keychain!
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