Note: As of September 2018 (release 2018.4) GPG Mail is no longer a free plug-in for Apple Mail, and comes with a $25 fee for support for the current version.
Here we will look at how to send and receive encrypted and/or signed emails using Apple Mail with the GPGMail add-on.
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Note: As of September 2018 (release 2018.4) GPG Mail is no longer a free plug-in for Apple Mail, and comes with a $25 fee for support for the current version. Here we will look at how to send and receive encrypted and/or signed emails using Apple Mail with the GPGMail add-on. Use GPG Suite to encrypt, decrypt, sign and verify files or messages. Manage your GPG Keychain with a few simple clicks and experience the full power of GPG easier than ever before.
Contents
- Reading your first encrypted message
Before we begin…
If you have not already installed GPGTools you should go back and do that first before trying to carry out the instructions on this page.
Sending your first encrypted message
Note: At some points in this process you could be asked for the passphrase you used to create your key. This is to ensure you are the authorised user of the key.
To test that everything is working as it should be, you can send an encrypted message to yourself.
Open Mail and begin a new message addressed to yourself.
If Mail detects that it has a public key for the address you are sending to, then the lock icon just above the text of your message will appear black and will be selectable. Otherwise it will appear grey. Click the lock to close it as shown in the image below.
This indicates that the message will be encrypted. At the same time the OpenPGP icon at the top right of the window will turn green.
The icon to the right of the lock is for signing messages, we will come to this later.
You can now click Send and your message will be sent to you.
Reading your first encrypted message
You should find your encrypted message arrives quite quickly (it hasn’t had to go far!).
Click on it as you would any other message and you should see your message as below.
You might be asked to enter your passphrase when decrypting messages. You can always save your passphrase in the OS X keychain if you are confident your machine is secure and nobody could send messages on your behalf.
Your message will look very much like it did when you created it. They main thing to look for here is the line just above the message that says:
This shows that the email was encrypted when sent to you.
How do I know it was really encrypted?
This is a good question, and something you should check to satisfy yourself that it really was. Because the encryption is so well integrated with your email client, you never usually get to see the encrypted message.
To see the message as it was sent to the email servers, and also how it is stored on your machine:
Go to View > Message > Raw Source
A window will open to show you the message as it is stored on your computer.
We have excluded the message headers in the screen-shot above just to make the image smaller.
It is worth having a close look at this window to familiarise yourself with what is encrypted and what isn’t.
You will notice that sender, recipient and the subject line are not encrypted. This is necessary or it would not be possible to deliver your message (certainly in the case of recipient anyway). Do not put anything confidential in the subject of your emails.
However, the entire body of your message was encrypted and you will not see the text “This is my first encrypted message using Apple Mail, GPGMail and OpenPGP.” anywhere.
Note: Any attachments to your email (such as photographs or documents) will also be encoded with no further action on your part. Once they are decoded at the recipient end they will appear just as in an unencrypted message.
Sending your first signed message
Compose another message addressed to yourself similar to the one below.
This time, click the seal icon above and to the right of the body of your message so that is shows as selected (as below). This will tell Mail to sign the outgoing message. You can always send signed messages whether you have the public key of your recipients or not.
You can now click Send and your message will be sent to you.
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If you don’t want the signed option to be enabled for each new message by default, there is a way to turn this off by entering a command in the Terminal application.
To launch the Terminal application go to Applications > Utilities and click on Terminal.
You can copy and paste the following command directly in to Terminal.
Reading your first signed message
When you receive your signed email, open it and you should see a window similar to the one below.
Here you will notice that under the messages headers and just above the content you see the line:
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This tells you that the message was signed with the key for the email address mentioned.
If you click on the seal icon, a window like the one below appears to give you more information about the key used to sign the message.
If you receive signed emails from people whose public key you do not have, this may read “unknown key”. Keys have an ID number and Mail may try to download the relevant key from the key servers so that it can identify the sender. If it can find the key it will be added to your key chain.
As with the encrypted message, it is worth looking at the source code of the email so that you are aware of what signed emails look like in their “raw” format.
At first glance the source code looks similar to the encrypted message code. However, you will notice that the content of the message “This is my first signed message using Apple Mail, GPGMail and OpenPGP.” is now visible and not encrypted.
At the bottom of the email is a black of text starting with “—BEGIN PGP SIGNATURE___”. This is the OpenPGP signature that is used to verify the message is sent from you. In addition, the signature is based on the content of the message and so if the message is changed or tampered with before you read it the signature will be invalid and your email client will tell you this.
Note: You can encrypt and sign messages at the same time.
Start sending messages to people other than yourself
Now that you know how to encrypt and sign messages, you can start sending messages to everyone, right?
Well, perhaps not right away. There are a few things to consider first.
- You can sign messages with your own public key without needing the public keys of your recipients.
- Some people who use certain email clients or some webmail services will have problems reading any part of your signed messages.
- You can only encrypt messages to others if you have their public key.
- Others can only send encrypted messages to you if they have your public key.
Item 1 is not a problem, you already have your own key.
Item 2 can be a problem, and more information is available in our document Using OpenPGP – Some things you need to know.
Items 3 and 4 are easily addressed by uploading public keys to a key server. This makes it very easy for others to find your public key so they can send you encrypted messages. Depending on the configuration, Mail with GPGMail will try to automatically download the public keys of people who send you signed and encrypted messages so that they are available for you to use. This can only happen if others have also uploaded their public keys to a key server.
If a key is not available from a key server, you will have to ask the person who owns that key to send it to you.
Unlike the software developed for Windows system, most of the applications installed in Mac OS X generally can be removed with relative ease. GPGMail is a third party application that provides additional functionality to OS X system and enjoys a popularity among Mac users. However, instead of installing it by dragging its icon to the Application folder, uninstalling GPGMail may need you to do more than a simple drag-and-drop to the Trash.
Download Mac App RemoverWhen installed, GPGMail creates files in several locations. Generally, its additional files, such as preference files and application support files, still remains on the hard drive after you delete GPGMail from the Application folder, in case that the next time you decide to reinstall it, the settings of this program still be kept. But if you are trying to uninstall GPGMail in full and free up your disk space, removing all its components is highly necessary. Continue reading this article to learn about the proper methods for uninstalling GPGMail .
Manually uninstall GPGMail step by step:
Most applications in Mac OS X are bundles that contain all, or at least most, of the files needed to run the application, that is to say, they are self-contained. Thus, different from the program uninstall method of using the control panel in Windows, Mac users can easily drag any unwanted application to the Trash and then the removal process is started. Despite that, you should also be aware that removing an unbundled application by moving it into the Trash leave behind some of its components on your Mac. To fully get rid of GPGMail from your Mac, you can manually follow these steps:
1. Terminate GPGMail process(es) via Activity Monitor
Before uninstalling GPGMail , you’d better quit this application and end all its processes. If GPGMail is frozen, you can press Cmd +Opt + Esc, select GPGMail in the pop-up windows and click Force Quit to quit this program (this shortcut for force quit works for the application that appears but not for its hidden processes).
Open Activity Monitor in the Utilities folder in Launchpad, and select All Processes on the drop-down menu at the top of the window. Select the process(es) associated with GPGMail in the list, click Quit Process icon in the left corner of the window, and click Quit in the pop-up dialog box (if that doesn’t work, then try Force Quit).
2. Delete GPGMail application using the Trash
First of all, make sure to log into your Mac with an administrator account, or you will be asked for a password when you try to delete something.
Open the Applications folder in the Finder (if it doesn’t appear in the sidebar, go to the Menu Bar, open the “Go” menu, and select Applications in the list), search for GPGMail application by typing its name in the search field, and then drag it to the Trash (in the dock) to begin the uninstall process. Alternatively you can also click on the GPGMail icon/folder and move it to the Trash by pressing Cmd + Del or choosing the File and Move to Trash commands.
For the applications that are installed from the App Store, you can simply go to the Launchpad, search for the application, click and hold its icon with your mouse button (or hold down the Option key), then the icon will wiggle and show the “X” in its left upper corner. Click the “X” and click Delete in the confirmation dialog.
Download Mac App Remover3. Remove all components related to GPGMail in Finder
Though GPGMail has been deleted to the Trash, its lingering files, logs, caches and other miscellaneous contents may stay on the hard disk. For complete removal of GPGMail , you can manually detect and clean out all components associated with this application. You can search for the relevant names using Spotlight. Those preference files of GPGMail can be found in the Preferences folder within your user’s library folder (~/Library/Preferences) or the system-wide Library located at the root of the system volume (/Library/Preferences/), while the support files are located in '~/Library/Application Support/' or '/Library/Application Support/'.
Open the Finder, go to the Menu Bar, open the “Go” menu, select the entry:|Go to Folder... and then enter the path of the Application Support folder:~/Library
Search for any files or folders with the program’s name or developer’s name in the ~/Library/Preferences/, ~/Library/Application Support/ and ~/Library/Caches/ folders. Right click on those items and click Move to Trash to delete them.
Meanwhile, search for the following locations to delete associated items:
- /Library/Preferences/
- /Library/Application Support/
- /Library/Caches/
Besides, there may be some kernel extensions or hidden files that are not obvious to find. In that case, you can do a Google search about the components for GPGMail . Usually kernel extensions are located in in /System/Library/Extensions and end with the extension .kext, while hidden files are mostly located in your home folder. You can use Terminal (inside Applications/Utilities) to list the contents of the directory in question and delete the offending item.
4. Empty the Trash to fully remove GPGMail
If you are determined to delete GPGMail permanently, the last thing you need to do is emptying the Trash. To completely empty your trash can, you can right click on the Trash in the dock and choose Empty Trash, or simply choose Empty Trash under the Finder menu (Notice: you can not undo this act, so make sure that you haven’t mistakenly deleted anything before doing this act. If you change your mind, before emptying the Trash, you can right click on the items in the Trash and choose Put Back in the list). In case you cannot empty the Trash, reboot your Mac.
Download Mac App RemoverTips for the app with default uninstall utility:
You may not notice that, there are a few of Mac applications that come with dedicated uninstallation programs. Though the method mentioned above can solve the most app uninstall problems, you can still go for its installation disk or the application folder or package to check if the app has its own uninstaller first. If so, just run such an app and follow the prompts to uninstall properly. After that, search for related files to make sure if the app and its additional files are fully deleted from your Mac.
Automatically uninstall GPGMail with MacRemover (recommended):
No doubt that uninstalling programs in Mac system has been much simpler than in Windows system. But it still may seem a little tedious and time-consuming for those OS X beginners to manually remove GPGMail and totally clean out all its remnants. Why not try an easier and faster way to thoroughly remove it?
If you intend to save your time and energy in uninstalling GPGMail , or you encounter some specific problems in deleting it to the Trash, or even you are not sure which files or folders belong to GPGMail , you can turn to a professional third-party uninstaller to resolve troubles. Here MacRemover is recommended for you to accomplish GPGMail uninstall within three simple steps. MacRemover is a lite but powerful uninstaller utility that helps you thoroughly remove unwanted, corrupted or incompatible apps from your Mac. Now let’s see how it works to complete GPGMail removal task.
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1. Download MacRemover and install it by dragging its icon to the application folder.
2. Launch MacRemover in the dock or Launchpad, select GPGMail appearing on the interface, and click Run Analysis button to proceed.
3. Review GPGMail files or folders, click Complete Uninstall button and then click Yes in the pup-up dialog box to confirm GPGMail removal.
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The whole uninstall process may takes even less than one minute to finish, and then all items associated with GPGMail has been successfully removed from your Mac!
Benefits of using MacRemover:
MacRemover has a friendly and simply interface and even the first-time users can easily operate any unwanted program uninstallation. With its unique Smart Analytic System, MacRemover is capable of quickly locating every associated components of GPGMail and safely deleting them within a few clicks. Thoroughly uninstalling GPGMail from your mac with MacRemover becomes incredibly straightforward and speedy, right? You don’t need to check the Library or manually remove its additional files. Actually, all you need to do is a select-and-delete move. As MacRemover comes in handy to all those who want to get rid of any unwanted programs without any hassle, you’re welcome to download it and enjoy the excellent user experience right now!
This article provides you two methods (both manually and automatically) to properly and quickly uninstall GPGMail , and either of them works for most of the apps on your Mac. If you confront any difficulty in uninstalling any unwanted application/software, don’t hesitate to apply this automatic tool and resolve your troubles.
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