@linnaroa Could you define out the question further?  Are you looking to re-use this Bulk Send process at a later time or would this be a one tine send?  Are you trying to send this one Recipient multiple envelope or just a single envelope?  Typically Bulk Send would be used to send a document to intended Recipients to take an action, such as a non-disclosure document. If you had 50 employees who needed to individually take action and then you wanted the Legal dept to get a copy, you would create a Template or Envelope that had the Legal dept set as Recipient #2 with “Receives a Copy” and Recipient #1 would be where the Bulk Send CSV would be used to specify the employee who needed to sign the document, therefore you would be sending 50 envelopes, each envelope with a unique Recipient #1 but the same Recipient #2.

I am sending 20 engagement letters under different entities to the same recipient to sign and date each letter. I was hoping to add the signature box and date at the same time instead of one by one. 

@linnaroa Thank you for clarifying, create a Template which is the best route if you intend to possibly use this scenario in the future, but you can also just create an envelope and set tags (DocuSign fields) which would apply to all envelope sent via Bulk Send.

Thank David! I appreciate your time and help! I will try this with the Bulk Send feature.