Paperless Office Output is not Generating All pdf's for Invoicing

We recently ungraded to Windows 10.  And it appears since doing this there has been something strange occurring when doing our daily invoicing.

When invoicing we choose Paperless Office Output "Print/PDF or Electronically Deliver".    When the pdf file is generated it does not contain all invoices that should be pdf'd.  It appears to be emailing all that it should.