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What finally solved my issue was deleting the contact as a whole - also from deleted items - and recreating it from a signed message of the recipient: Go to File, Options, click on Mail, scroll down until you see Send Messages and then click on Empty Auto-Complete List. Compose an encrypted email using the GAL to find the person you want to send to, once you have them in the To: box Right click on the name and Add to Outlook Contacts. Somehow, Outlook can default to an older certificate, so if you are updating a certificate the easiest thing to do is delete any pre-existing certificates for the contact in question so that when you import the new certificate it will be the only one.