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custom Ribbon button grey

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So my company has asked me to use outlook today. I finished generating a new secure certificate with comodo and successfully sent some encrypted mail to a coworker.

Now I'm a bit confused on the ribbon system.

I added the "encrypt" and "sign" buttons to a custom ribbon group which i labeled "security". It was surprisingly hard to find these buttons buried in the "all" section.

I did this because this process was tedious and I don't want to do it every other email for the rest of my life.:

"File"->"Properties"->"Security Settings"  

Check the encrypt box...

Select "My S/MIME settings" on the drop down menu...

So now I have these buttons, but they are grey and I can't do anything with them at all.

Is there something I need to do to activate them? If not can I write a macro to perform the above actions with a one click toggle?

Thanks,

Jason


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