I am using a standalone Outlook 2010 client with Outlook Anywhere (RPC over 443) to connect to an enterprise exchange environment. I have certificates and have configured Outlook to sign all email and also selected the option to "Send clear text signed messages when sending signed messages".

When email arrives it is displayed with the blue lock icon (encrypted) instead of the red signed ribbon. It seems the clear text option is not working?

Using the same certificates from a domain client seems to work properly so I don't believe it's a certificate issue. I've tried comparing Outlook client settings but haven't found anything yet.

I'm not sure where else to look, any ideas or help would be much appreciated. 

Thank you,

Scott

Did you check if option for mail encryption is turned off? Also, in order to send encrypted email you must have access to the recipient's public key (usually via GAL). To whom do you try to send emails? And, is recipient able to open the email from you?

Hi,

From your description, the Exchange server seems to be ok. So I recommend you post the thread to Office forum:

http://social.technet.microsoft.com/Forums/en-US/home?forum=outlook

Best regards,
Belinda