Encrypted email does not get sent

[Migration User]

I installed Symantec™ Encryption Desktop for Windows  to encrypt email using Outlook 2007 and the hard drive.  

When I send an email to an address that is in the global directory the email is encrypted, it's sent and arrives and is decrypted the way that it should

If I send an email to an address that is not in the global directory it arrives unencrypted like it should

If I send an email to 2 addresses, 1 in the global directory and 1 not in the directory.  The email arrives only at the email address that is not in the directory, i.e. unencrypted.  The one in the directory, encrypted, disappears even though PGP says it sent one to each

Here is an edited version of the log

20:40:56 Email       Info      Processing outgoing message from MY NAMEHERE <[e-mail]> with subject: encrypted email address 1st
20:40:56 Email       Info      Need passphrase for key 0xE8828BB8; asking user
20:41:47 Email       Info      Received good passphrase from user
20:41:53 Email       Info         Sending unsecured message to [e-mail]
20:41:55 Email       Info         Encrypting PGP/MIME message to [e-mail] with key(s):
20:41:55 Email       Info            'me <[e-mail]>' (0xE8828BB8:0xC89D1840)
20:41:55 Email       Info         Signing PGP/MIME message with key 'me <[e-mail]>' (0xE8828BB8)

The log does not contain anything about the encrypted email being sent

Thanks for the help

[_Adam_]

Hi,

Do you use a Standalone or managed PGP client. What version please ?

I guess is Standalone - are you able to turn on debug mode ON resend messages, capture logs and post them over here.

HOW TO: Add Debug Level Logging on Windows 7 for Symatec Encryption Desktop (previously PGP Desktop)
http://www.symantec.com/docs/HOWTO64205

[Migration User]

The Debug logs state which policies it matches against, very handy.  Post the debug logs as per Adams comments and you should be able to see where it's falling.

[Migration User]

Yes it is standalone.  I've included the log, hope it helps.  I don't see where there is an error.

 

 

Attachment(s)

PGP Log.txt   145 KB 1 version

[Migration User]

Hmm.

 

It says its being sent, 1 encrypted and 1 unencrypted.  Does this go straight to MX records or do you have an exchange server?  The email must be blocked somewhere along the line.  

[_Adam_]

and also... have a look into this:

http://technet.microsoft.com/en-us/library/dn305950(v=exchg.150).aspx

 

[Migration User]

There is no Exchange Server, it goes straight to the MX record.  In this case Google.

[Migration User]

There is a question from Google

 

They want to know if the Message ID is the same in both emails.

So my question is when PGP encrypts the email does it send both messages with the same Message id or does it give a unique id to each email.  Is there something in the log that indicates that?

 

Thx

[Migration User]

The message ID stays the same: 

19:59:49 Email	 Raw	(11): Message-ID: <000001cfd86c$b79cd510$26d67f30$@com>

[Migration User]

Here is an update, not sure it helps

 

The 2 email address that I was sending to both resided on Gmail.  I created another account outside of Gmail, sent a test message 1 to the encrypted address, hosted by Gmail, the 2nd address not encrypted and outside of Gmail.  Both were received

Sent yet another email to 3 addresses 
1 encrypted, hosted by gmail
1 unencrypted, hosted by Gmail
1 unencrypted, hosted outside of Gmail

The 2 unencrypted email addresses received the message, the encrypted address did not receive the email

Looks like the problem only occurs when encrypted email is sent through Gmail and there is a mixture of encrypted and unencrypted addresses