Hi @Rob Roach ,
Whether this issue happens to all users?
1.Make sure that for sending emails via workflow that the user's login is entered (via workflow lookup) as type Display or Email.
2.Make sure that the user's profile information in UPS is complete. In particular, verify that the user has an email entered into his or her UPS profile.
3.If any changes to the user's profile information in UPS are made, followup with full crawls of both user profiles and My Sites content.
For more detials: The e-mail message cannot be sent. Make sure the outgoing e-mail settings for the server are configured correctly.
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