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Problems with Email Encryption

Created: 10 Dec 2012 | 4 comments

I cannot get PGP Desktop 10.2.1 MP5 to encrypt any email on OS X 10.8.2 using Mail.app 6.2.

I have created the keys, the services for all my imap accounts and it seems to be intercepting email OK on the inbound route, however, no matter what I do to try and encrypt an outbound email, it does not work. On the log, even in debug mode, the outbound email seems to zip through and not even cause 1 line of logging. It sends fine. When I receive it (sending to myself - with the cert I use for signing and encrypting) PGP scans the incoming email for certs etc. and does not find anything - all that, however, does show up in the log.

I really need some advice on this as it's driving me nuts.

When I set up the services in Encryption Desktop I set it to Discover to begin with, and all the services it created were just rubbish - the email addresses were all wrong, the servers all came up as bizarre IP addresses and no matter what I did they would not resolve to my very simple settings in the mail app.

I then removed all of those auto services and configured them all manually. They all have default policies.

If anyone has a simple How To guide that I can follow to try and get this damned thing working, I would be most grateful.

TC

Comments 4 CommentsJump to latest comment

Tom Mc's picture

These Knowledge Base Articles may help:

http://www.symantec.com/docs/TECH149518
http://www.symantec.com/docs/TECH149132

Please check to see that PGP is using a currently valid license.  I mention this because when it isn't, it functions as freeware; the freeware will use the email proxy for incoming email, but not for outgoing.

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Timothy Claypole's picture

Hi Tom,

Thanks for replying so quickly. I just bought the license and activated it so it's literally just new and I signed up for 2 years so no problem there.

I'll take a look at those two links and see if they help at all.

Regards

TC

Timothy Claypole's picture

Hi Tom,

Just following up on that 2nd link it says that the supported Apple Mail version is:

Apple Mail 4.5

As I am on Mountain Lion the Mail app is automatically on 6.2. However, when I read the release notes for Encryption Desktop 10.2.1 it says it's compatible with Mountain Lion, so how does that work?

Am I simply unable to use Mac Mail 6.2 with PGP, or is that a combination that should, in theory, work?

TC

Tom Mc's picture

According to http://www.symantec.com/docs/TECH191290 Apple Mail 5.2 isn't even supported yet.  Not yet being supported means that it has not yet been successfully tested as being compatible, but does not mean that it definitely will not work for you.  Maybe others here can report whether they have successfully used the email proxy with your version.

You must not be using any other email proxy - any chance you are using any scanning of outgoing email to block accidentally sending personal information?

When you consider your issue resolved, please click Mark As Solution on the most helpful response.

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