Mark will like this. Paperless uses a 3rd party called Chilkat Mail to do the actual emailing. I've actually used Chilkat separately in a script to send an instant notification email instead of Biz Alerts, K-Sync. Anyway the data in Company Maint / SMTP tab is formatted and sent to the Chilkat object (DLL) via Sy_PdfConverter.pvc. Chilkat does support TLS and SSL but Sy_PdfConverter.pvc does not have the hooks in it to send the TLS/SSL fields to Google Apps and such. If Sage ends up supporting it they will need to provide:
1) New version of ChilkatMailMain DLL during Wkstn Setup that supports the different permutations of SSL / TLS that are out there today.
2) Additional field in Company Maintenance related to SSL / TLS
3) New version of Sy_PDFConverter.pvc that has SSL / TLS hooks and handles the different permutations.