Problems encrypting with Outlook 2007

I just installed CSE, I am attempting to send an encrypted email for single use. When I attempt to send the message, I get the following outlook message.

Microsoft Office Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities. Continue will encrypt and send the message but the listed recipients may not be able to read it.

Continue is greyed out, I can only send unencrypted or cancel. Maybe I am not using this correctly. I want to send an encrypted email to someone that doesn’t currently have CSE.


FYI, Using Outlook only mode

Another follow up. I am able to encrypt some messages to certain people, in different domains. Haven’t been able to encrypt a message to someone on my domain and haven’t been able to encrypt to one of my personal email addresses.

Also, One address I tried, I had never emailed before and it wasn’t in my address book. It was a new Yahoo account I setup to try this.

Well, while I am having a conversation with myself here, I think I may have found the problem.
I used a custom settings config for comodo and when typing the email, don’t click on Signature or Encrypt. It doesn’t send the email with any padlocks or anything, but I get the results I expect at the other end. Now, the problem is, I tried to forward the email to the address it says in the instructions, to view the email online. Never get a response like it says you will. Also downloaded comodo on the recipients computer and it doesn’t seem to decrypt the message at all.

This is really not a simple solution for encrypting emails. I need this to work effortlessly for my employees to be able to encrypt emails to their clients. It is far to unpredictable and difficult to use on the receiving end…so far…