Update certificate in Outlook contacts

How can I update an encryption security in Outlook contacts?

I got an email signed with an updated certificate by someone who is already in my contacts with an expired certificate.

If I REPLY to that email, I can encrypt my reply and it works. However, if I try to make a new email to the same contact it does not work.

If I right-click on the From: field of the new email from the contact, and choose Add to Contacts, in other words try to create a brand new contact record (with the new certificate), it does not create a new Contact, it just brings up the old contact record with the old, expired certificate in it.

Solution 1:

The option to update the contact with the new certificate no longer exists in the newest Outlook version (2016/365). This was available for 2007/2010/2013.

You must delete the contact containing the old certificate, and then add the contact anew.