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

• Edited by gawnesco Saturday, September 21, 2013 11:37 AM more detailed subject

Hi,

Please test in Safe Mode, to determine if it's 3rd-party add-ins related:

Press Win + R and type outlook.exe /safe in the blank box, then press Enter.
If theres no problem in Safe Mode, disable the suspicious add-ins to verify which add-ins caused this issue.

Also make sure you have installed all the updates and hotfixes.

Regards.

Melon Chen
TechNet Community Support