We setup our nice new SQL 2016 SSRS servers to authenticate using the new SQL 2016 GUI which just supports it now. One problem with the GUI is that it requires that you use encryption. No big deal, SendGrid supports encrypted SMTP.
The problem with SendGrids encrypted SMTP is that it has a funky certificate chain which isn’t trusted by default. And it’s a convoluted process to get the correct certificate chain installed on a few servers (we have an SSRS farm as there’s thousands of reports being delivered every morning).
Click through for the solution.