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Windows Server 2016 Essentials Health Reports Failing due to TLS 1.0 Deprecation

PJV 6 Reputation points
2022-03-14T22:09:35.823+00:00

What is the preferred solution to Microsoft deprecating TLS 1.0 and 1.1, yet Server 2016 Essentials relying on those protocols to send Health Reports?

The only solution I've seen posted requires either the installation of a third party tool (as suggested by "TheOfficeMaven.com) ...or, using something like Direct Send, to work around using any encryption and going over Port 25 ...which a lot of ISPs block nowadays.

Why is Microsoft silent on an issue affecting a supported server OS?

Windows Server
Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
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  1. Limitless Technology 39,446 Reputation points
    2022-03-18T15:01:19.32+00:00

    Hi @PJV

    There are reports on this and several users have come out with some workarounds which have pretty much sorted this, some of them are listed below try out these and check if they are helpful.

    Check if it is possible to use another email account (which supports TLS 1.0) instead of Office 365 to send the health report.

    The workaround would also be to specify the MX for your domain at Office 365 as the SMTP server, port 25 with no auth or SSL/TLS. Since it's only emailing you, it's not relaying and it will be delivering the health report.

    Here is a thread as well that discusses the same issue and you can try out some steps from this and see if that helps you to sort the Issue.

    https://learn.microsoft.com/en-us/answers/questions/120229/wse-health-reports-office-365-and-tls-12.html

    Hope this resolves your Query!!

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