How to resolve error "Microsoft Outlook cannot sign or encrypt this message" when sending encrypted email.

Invalid Certificate
Microsoft Outlook cannot sign or encrypt this message because there are no certificates which can be used to send from this email address 'Lname.Lname@dot.nm.gov'. Either get a new digital ID to use with this account, or use the Accounts button to send the message using an account that you have certificates for.

Outlook for the Web

Try to send the encrypted email using Outlook for the Web at https://outlook.office365.com/mail/.

Outlook for the Desktop

In Outlook, go to the top left File menu and then click on the bottom right "Options".

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Click on Trust Center and then Trust Center Settings...

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Select "Email Security" and verify the options to encrypt and sign are UNCHECKED. Click OK to exit through all of the dialogs.

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Try sending the encrypted email again using the instructions here:  How to send an encrypted email message.

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