Hi ​@Derek Wishart !

If I understand correctly, you want to upload different files and have each recipient sign a different one, right?

The platform does not originally offer this option. What we currently offer is that you can customize the email that the recipient receives to sign, allowing you to "translate" the message, but this does not apply to documents (files). See this article for more information: Custom Language and Email Messages for Recipients

An alternative would be to use the Document Visibility feature, but it is worth noting that each recipient will sign a different file, and it is not possible to consolidate the signatures in the end into a single file. To use Document Visibility, check if your account plan has this feature included, and check this article: Set Document Visibility

Please, let me know if I was able to help you with this question. If so, could you please select click on the "Select as Best" option? Thank you!

Hello ​@Derek Wishart,
 

I hope you are doing well. 
I want to confirm if you were able to solve your issue by utilizing the suggested solution or if the information provided was useful.
Let me know, and I will gladly help you address the situation as soon as possible.

Ma. Cassandra | Docusign Community Moderator
Mark as “Best Answer” if this helped clarify things.