How to send and receive encrypted emails macOS Sierra

Problems caused by operating system upgrades

As is often the case when there is an upgrade to the Mac operating system something gets broken. There are bound to be one of two things that don’t get checked when the company is sending out the beta versions of the new operating system. Some things are not quite so important to the beta testing group. This may be the case with encryption of emails. In the latest version of the Apple operating system macOS Sierra the mail application has been broken. When we had the update to El Capitan we were lucky that nothing stopped working as far as encryption was concerned. This was just as well because on the previous upgrade two years ago the GPG plug-ins for mail stopped working. This was particularly annoying because it took the people who made the plug-in and GPG keychain a long time to fix the problem. I’m keeping my fingers crossed that we don’t have to wait so long in order to have the use of GPG in the latest Apple Mail application. I want to send encrypted emails macOS Sierra.

If GPG is not working then for some of us who care about encryption we can just start using S/Mime instead of GPG until we get a fix. It’s not possible with the version of Mail in Sierra because the S/Mime has also been broken. Sometimes you wonder if it is worthwhile upgrading to latest versions of the operating system on day one. Maybe we should all let the dust settle and make the jump after three or four months. The only difficulty with that scenario is if everybody did that, then no one would find out where the problems were. In Mail before I upgraded I was able to choose which encryption system I wanted to use. I could easily see when composing an email whether it was set for signing and encryption by whichever method. Now nothing works at all! What we need is a workaround.

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Using a workaround to send encrypted emails macOS Sierra

There are two possibilities if we still want to send encrypted email messages.

  1. Stop using the Mail app and you something else like Postbox or Thunderbird
  2. Continue using GPG Keychain and use the services menu to encrypt selected text. Or we can encrypt the whole text file or picture or whatever and add it as an attachment to our mail message.


I tried installing Thunderbird and it didn’t go very well and I gave up. I used to have version 4 of Postbox and there has been an upgrade to version 5. I had stopped using Postbox even though it had many more facilities within it compared to Apple Mail App. There were times when it just didn’t work correctly and so I went back to using Mail. So I downloaded version 5 and if I want to continue using it then I will have to pay to upgrade. At the moment I’m in the testing phase because I don’t really want to spend out €26 to buy the application if it’s not going to give me what I need. There are some really good useful tools within Postbox. It’s particularly good if you want to find messages within a mail folder that are unread, starred or favourited as well as a few other helpful ways of searching. I could for example tell it to look inside a folder for all of the emails received within the past week or for the past day. Postbox does work with the plug-in called Enigmail, so I can use GPG encryption. It’s also possible to send and receive email using S/Mime certificates to send encrypted emails macOS Sierra.

Getting set up with encryption certificates from Start SSL

Email Encryption certificatesI have been using these certificates for a few years and it does take some learning in order to set them up to use. Once you have the certificates installed they are very easy-to-use and you don’t even have to think about encrypting mails. Since the last time I went to the website to create the certificates things have changed. There was a new process to go through to get the certificate and to install them onto your machine. It took some time to work out what I needed to do, but I got there in the end. I created for myself a Clarify Tutorial so I can follow it each time I need to go back and repeat the process. The process is a little bit convoluted and it’s easy to forget a stage along the way. Not any more, now I have this tutorial. So you can use these certificates with Postbox. I don’t suppose it’s going to take too long before Apple release an update to Mail so we can use them within that application.

Manually encrypting text or files with GPG

This is an easy option to send encrypted emails macOS Sierra provided you’ve set up the services menu when you set up the GPG toolkit. If you didn’t do so, then don’t worry because it’s easy to go back into the services menu in system settings for your Mac and add those services.

Step-by-step guide to having these encryption services available on your Mac

Using the services menu to encrypt text

  1. Select the text you want to encrypt

  1. Right click or tap with two fingers on your trackpad to bring up the context sensitive menu.
  2. Scroll through the list until you get to OpenPGP: Encrypt Selection

  1. The window will pop-up for you to choose the key you wish to use. You will choose the public key of the person you are sending the message to. You should also include your own key in case you want to be able to decrypt and read the message you are just about to encrypt.

You can do this encrypted emails macOS Sierra from within the compose window of the Mail application. It’s not necessary any more to do it first in a text editor window. As well as choosing the public keys for the recipients you can also choose from your own key pair to sign whatever you are encrypting.

All you have to do when you’ve done all of this is to send the email off to its destination. The person receiving the email with the encrypted text will have no trouble in decrypting that text with their private key of their key pair.

Decrypting text within an email sent to you

  1. Select the block of encrypted text within the message.
  2. Right click or tap with two fingers on your trackpad to bring up the context sensitive menu
  3. Scroll through the list until you get to the OpenPGP: Decrypt Selection – Hey Presto, you see what was hidden by the GPG encryption.

encrypted emails macOS Sierra

Are you planning to send encrypted emails macOS Sierra from your computer?