I'm having the same issue. I went through all the steps and no matter how many times I check that the date field is enabled and the service date option is on in the Sales settings, the dates still do not appear anymore in the PDF preview or printouts. I also used to have a printout of the signature field captured through the mobile app that no longer shows up in the PDF when it used to before. I called the support number and spent half an hour with a Quickbooks associate over the phone while sharing screen through glimpse and repeating these same steps and again confirming everything is set, but the Date and signature still do not print anymore. As far as I can tell this product is buggy and broken on Quickbooks end and I am actively looking for a replacement.