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Appreciate your feedback here, everyone. While we've recently released contact group invoicing with new invoicing, the ability to attach and send an attachment has not changed for the time being.
Contact Group invoicing will only create draft invoices for the contacts within that group, so you'll need to attach any documents to the individual invoices that are created and select to include these with the invoice when sending.
We'll continue to review this idea as a future enhancement, and I'll let you know if there are any changes planned, here.
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I entirely agree with this as we have a similar issue. It may be easier (coding wise) to add the documents to the draft invoices rather than the spreadsheet. I imagine that this would be workable as long as we could add a single document to all / many of the draft invoices