Gmail uses multiple certificate names for SMTP and IMAP SSL certificates. Gmail also requires SSL to be enabled to connect to their mail servers. Symantec Encryption Desktop cannot proxy SSL traffic enabled within the mail client and causes problems with the connection.
Since Gmail uses multiple SMTP/IMAP servers and several different hostnames for the SSL certificates this causes multiple proxy services to be configured in Symantec Encryption Desktop, none of which will work.
You may be presented with a smiliar error to the following if you have SSL configured on the mail client. This means that you need to disable SSL in the Apple Mail client and then restart Mail.
This is due to the way Gmail handles the SSL certificates and having SSL enabled in the Apple Mail client instead of allowing Symantec Encryption Desktop to enable the SSL session. This requires you to setup on service with a * in the mail server settings to enable all the SSL certificates to that Gmail uses to work and proxy the connection.
1. Open Symantec Encryption Desktop by going to the finder App and clicking Applications > PGP.
2. Click PGP Messaging and delete any existing services configured there (they will typically have a service name something like this: pb-in-f108.1e100.net).
3. Click on Encryption Desktop and select Quit Encryption Desktop.
4. Open Apple Mail and go to the Mail account settings for the incoming mail server and outgoing mail servers found here:
Incoming Mail server (IMAP)
Note: If the Gmail account settings are not in there, configure them with the following information:
a) Description: Enter a name for the account
b) email address: Specify the Gmail account/email address that you wish to use such as: [email protected]
c) Full name: Your full name as you want it to appear on email
d) Incoming Mail Server: imap.gmail.com
e) User Name: Full gmail email address such as: [email protected]
f) Password: Gmail account password
g) Click on Advanced
Outgoing mail server (SMTP)
Server Name: smtp.gmail.com
Select Advanced and make sure that it's configured for custom port 587
5. Open PGP Desktop and select PGP Messaging.
6. Click on Create New Service.
7. Configure the mail service with the following settings:
Incoming Mail Server
Outgoing Mail Server
8. Click Ok
9. In Apple Mail, select Mailbox (top bar) and select "Take All Accounts Online"
You should see a prompt for Symantec Encryption Desktop asking you if you wish to secure the email.
If you are still seeing problems, a good place to troubleshoot is by turning on debug logging within Symantec Encryption Desktop. You can do so by opening Symantec Encryption Desktop and selecting Window then selecting Encryption Desktop Log. At the bottom of the screen where it says Logging Level, change that to debug. Then go back to Mail and go to Mailbox > Get all New Mail.
Mac OS X 10.7 and above
Symantec Encryption Desktop 10.2.1 MP4 and above
Apple Mail 5.2