SQL Database mail no longer working

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?

Microsoft SQL Server

Last Comment

Mel Brooks

8/22/2022 - Mon

David Favor

2/18/2022

Likely the receiving MTA has now enforced Always On Opportunistic TLS, which is an incredibly bad idea.

https://www.experts-exchange.com/questions/29233486/MSsqlserver-TLS.html provides details for debugging this using SWAKS.

Always better to test + know, than guess.

ASKER CERTIFIED SOLUTION

Mel Brooks

2/23/2022

THIS SOLUTION ONLY AVAILABLE TO MEMBERS.

View this solution by signing up for a free trial.

Members can start a 7-Day free trial and enjoy unlimited access to the platform.

See Pricing Options

Start Free Trial

GET A PERSONALIZED SOLUTION

Ask your own question & get feedback from real experts

Find out why thousands trust the EE community with their toughest problems.

Experts Exchange has (a) saved my job multiple times, (b) saved me hours, days, and even weeks of work, and often (c) makes me look like a superhero! This place is MAGIC!