We have SQL database mail configure on SQL Server 2012 SP4 hosted on Server 2012.
This is an Office 365 account and it was working fine up until a month ago and now I'm getting the error: "Must issue a STARTTLS command first". So what has changed?
I tried uninstalling the most recent Windows updates, but that did not resolve the problem. Any suggestions on how to get this working again?
https://www.experts-exchange.com/questions/29233486/MSsqlserver-TLS.html provides details for debugging this using SWAKS.
Always better to test + know, than guess.