70-339 Question #68: Real Exam Question with Answer & Explanation

Question

Options

• AConfigure the SMTP server to support the TLS 1.0, TLS 1.1. or TLS 1.2 protocols.
• BInstall a server certificate on the SharePoint Server.
• CConfigure the SMTP server to support the SSL 2.0 or SSL 3.0 protocols.
• DEnable STARTTLS encryption on the SharePoint Servers.
• EEnable STARTTLS encryption on the enterprise SMTP server.

Explanation

Enabling encrypted outgoing email in SharePoint 2016 via STARTTLS requires the enterprise SMTP server to both advertise the STARTTLS capability and support a compatible TLS protocol version.

Common mistakes.

• B. Outgoing email encryption in this context does not require a server certificate installed on the SharePoint Server itself; the TLS certificate requirement applies to the SMTP server that terminates the encrypted connection.
• C. SSL 2.0 and SSL 3.0 are cryptographically broken and deprecated protocols; SharePoint 2016 STARTTLS relies on TLS, not SSL, so configuring the SMTP server for SSL 2.0/3.0 would not establish a valid encrypted channel.
• D. In SharePoint 2016, STARTTLS behavior is governed by the outgoing email configuration and does not have a separate 'Enable STARTTLS' toggle on the SharePoint servers themselves; the required action is on the enterprise SMTP server side.

Concept tested. SharePoint 2016 outgoing SMTP encryption with STARTTLS and TLS

Reference. https://learn.microsoft.com/en-us/sharepoint/security-for-sharepoint-server/configure-email-integration

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