How to use PGP Encryption Desktop to automatically encrypt Gmail in Outlook with App Passwords (two-factor auth with OAuth - Symantec Encryption Desktop)
Article ID: 220878
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Issue/Introduction
Gmail requires some special configuration as Google does not allow third-party applications to be used, such as Outlook. As a result, there are some extra steps needed to do this. This article will go over these steps using multiple methods for PGP Encryption Desktop (Symantec Encryption Desktop).
Resolution
The announcement made by Google, concerning less secure apps does not affect the PGP Email Encryption with Gmail as per the Gmail community. Using an App password is still the current way and the way going forward to use Email Encryption with Gmail.
For further guidance on this topic, reach out to Symantec Encryption Support.
IMSFR-519/EPG-24509
For alternatives to Email Encryption and Decryption, see the following articles:
153463 - Using PGP Viewer to decrypt email messages encrypted with PGP content
For alternatives on how to encrypt files, which can then be attached to emails, see the following articles:
153161 - PGP Encryption Desktop: Encrypt or Decrypt Files and Folders with PGP Zip (Windows)
PGP Email Encryption and Decryption in Gmail
Method 1: Automatically Encrypted Email in Gmail
For this method, IMAP is required as Gmail configured in Outlook using the MAPI option is not true MAPI, which is something required for this to work. If you are using IMAP with Gmail, you can still automatically encrypt emails. See the attached documents on the bottom of this article for instructions on how to get this working with Gmail as there are some special steps due to Google requiring third-party applications to take some extra steps.
Method 2: Encrypting Emails using the Clipboard functionality.
This is a method to be able to encrypt the contents of what you've copied using ctrl+c. When you paste the encrypted contents the result will be cipher text.
Method 3:Encrypting using Current Window.
This feature allows you to encrypt the current window of a message. Gmail uses a web interface that Current Window doesn't work well with, so if you want to use the Current Window feature, you type the message in a text editor and then paste it. If you are using Outlook with Gmail, you can use the current window within the Outlook interface.
macOS may have some more specialization to get this to work, but they can be configured to work with Symantec Encryption Desktop.
For Method 1, see the attached documents for instructions on how to get Outlook configured with an App password as well as another document on how to configure macOS to work with Gmail.
For Methods 2, and 3, see the following steps.
If using the automatic email method is not possible, you can also use the "Current Window" or "Clipboard" functionality to encrypt text and then you can send the encrypted text in your email.
Consider the following example where you need to encrypt an email, but can't use IMAP:
The Current Window or Clipboard features can encrypt text, but due to the proprietary web type, you need to type the message in a text file first:
Once you type the message, highlight the whole message so it is highlighted so the Current Window feature has focus:
Note on Clipboard Feature: If you are using the Clipboard feature, you don't need to use the notepad method, you can just highlight and copy the text using "ctrl+c" and the text will be saved to your clipboard. You can then encrypt the clipboard in memory and then you will be able to paste the encrypted text. See the next steps for more details.
Now click the lock icon by the time in the bottom right-hand corner of the computer screen:
Select the option to Encrypt, or Encrypt and Sign from the menu.
Note on Clipboard Feature: In the screenshot above there is also Clipboard feature that will encrypt what is currently copied in clipboard. If you want to encrypt the clipboard, highlight the text you wish to encrypt, press "ctrl+c" to copy, and then select Current Window to Encrypt. When you paste the text, it will paste the encrypted content for your recipient. This option is often times easier than the "Current Window" feature.
Select the key you wish to encrypt to. In this example, we have only one key from the selection dialog. Drag the key to the bottom, which will encrypt to this key:
If you are using the Current Window feature with the text file, you will see the regular text get encrypted and the result will be cipher text:
Note on Clipboard Feature: If you used the Clipboard feature to encrypt the contents of what you copied (ctrl+c), then you will simply paste the encrypted contents into your gmail message:
If you have files you need to encrypt, you can encrypt the files individually and attach them. For information on how to encrypt individual files, see the following article:
178739 - HOW TO: Encrypt Files and Folders with Symantec Encryption Desktop 10.x for Windows
Additional Information
See the following article for some other ideas on how to configure email clients to work with PGP:
191087 - How to configure Symantec Encryption Desktop to automatically encrypt Gmail in Outlook
ISFR-1821, ISFR-1877
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