I have the same issue. I am working with Manager 23.10.13.1050 and the new Mac Sonoma Operating System. Before installing the latest OS update, I would select the Print Button and Manager would put a pdf copy of the invoice in the Drafts folder of Apple Mail. This function is no longer working. I am including the error message I received on my computer. Now I have to save the invoice as a pdf and attach it to the email. Not a big deal, but the Send in Mail was a very convenient feature.
That is not a Manager issue. It is a characteristic of your new operating system or its setup.