Update Existing Content
I'm currently using 'Salesforce Files' which creates a content record for the DDP. Salesforce supports content versioning making it easy for users to 'attach a new version' however this isn't supported in Drawloop.
It would be next level, if you could give us options to insert a new file, but if it exists, update the content. This would give us one static URL to the content and make navigating our Notes & Attachments sections much easier!

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Kevin Crews commented
This would also solve a big problem for me. When a user runs a document package, I have an insert-update to submit the record for approval. The approver reviews the record and the docs. This works very well when the record/docs are approved. But if they are rejected, and then the user makes corrections and generates the document a second time, the new document attaches as a new file -- so now I have the old (rejected) doc and the new doc visible.
I'd prefer that the new document replace the prior document as a new version.