@Natalie Wilkinson How exactly did you delegate access to the bosses envelopes? There is shared access, delegation, and just correcting any envelopes (if internal) to the No. 2 individual. Shared Access was not meant to be a process in which the User shared can sign on behalf of the shared user. Delegation as I understand it is setup by the User who is going out of office and that envelope should land in the delegate’s Inbox if the delegation was setup prior to the envelope being assigned to the original Recipient, so its possible the delegation was not in place prior to the assignment to the boss. I would look at potentially correcting the envelope and changing the Recipient from the boss to the No/2, which is possible if the envelope was sent from the same account where you or someone in your office is the DocuSign Admin.