If you manually typed an address into the To: field, you sent tracked and the email was never delivered, then there are a couple of possible reasons.

  1. If you sent this email to yourself, see this article
  2. The “nicklist list” that is used for the auto-complete in the To: field has an error
    This could happen due to an address change, or an active directory group change on the Exchange Server, or a previous input error. Follow the process below to reset/rebuild your nickname list.

    The reason this occurs (but works when you send a regular Outlook email not tracked by PoliteMail, is because PoliteMail doesn’t have access to all the internal functions of Outlook, it requires an SMTP email address (an address in the form “name@domain.com”) in order to be able to send successfully. Outlook however, can use a network address or Exchange address to reference the updated email, and successfully deliver the email. If you double-click on the name in the To: field and get an Outlook error dialog that says something like “The entry could not be found, the address has moved” this is likely the problem – as PoliteMail would not have a handle to the updated SMTP address.

Use this Microsoft support article to fix it: How to reset your nickname/auto-complete list