Endpoint Encryption

I'm having trouble sending encrypted emails. They're just going out as normal emails, despite my using the default option of putting '[PGP]' in the subject line. However, I can decrypt my counterpart's emails with no problems. I know that the desktop doesn't work with webmail, so I'm accessing my emails through Outlook instead. Could that be the problem? I don't get an error message of any kind; they just get sent as normal emails. Any help would be greatly appreciated, as I'm on a 30-day trial and wasting lots of time with this issue!

It sounds like you are both sending and receiving your email via Outlook?  This should not present a problem.  Are you using a licensed version of PGP?  I ask this because when using the Freeware, the email proxy will work to decrypt incoming email, but will not encrypt outgoing email.  Please see this Knowledge Base Article.  You must not let any other email proxy be in use, or this would conflict with PGP's email proxy.

Have you made any changes to the default PGP messenging policies?  I ask, because you are attempting to use the Required Encryption default policy, so it must both be enabled, and listed above the default Opportunistic policy.

Yes, I'm both sending and receiving email via Outlook (but the underlying email account is a Hotmail account). The version is definitely licensed, as I downloaded it from Symantec's website.

I've played around with the messaging policies, but nothing I've tried seems to work. I've tried having the default "[PGP] and/or confidential" policy as the only policy enabled. And I've tried creating my own policy where only "[PGP]" in the subject line is needed (with that, too, as the only policy enabled). All to no avail thus far...

Please go to About PGP Desktop, from either PGPtray or the Help Menu in PGP Desktop, click on the license button to check if it is showing as currently licensed, and if PGP Messaging is shown as enabled.  There is no need to have the messaging policies other than the default setup.

It says that there are 20 days left in the evaluation period. And PGP Messaging is ticked/enabled.

Please make sure you have returned the messaging policies to their default setup, and that on the messaging tab of PGP Options that you have enabled Discover New Accounts.  Also make sure you are using some other email proxy for scanning outgoing email, such as those set up to prevent the sending of personal information.  In the PGP Messaging section of PGP Desktop, click on your messaging service, and then on the right hand side, click on Server Settings, and make sure the settings are correct.  It may help to delete the messaging service, and let PGP recreate it.

Hi Tom. Discover New Accounts is enabled. I've got McAfee Security Center running, so I've just tried switching off real-time scanning and sending an email. The log doesn't seem to suggest that the email was encrypted. I've just checked the server settings and at first glance they seem ok. (Not that I really know what I'm looking for.) "Server type" is "internet mail"; "Incoming mail server" is "Automatic (POP, IMAP)"; "SSL/TLS" is "Automatic", and the box marked "Warn if client attempts SSL/TLS" is ticked.

There's nothing that my counterpart would need to do, is there? It couldn't be because she hasn't verified my key, or hasn't uploaded her key to the Global Directory?

I've just tried deleting the messaging service and recreating it - seemingly without success.