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Sage 100: Sage 100 2018 and older email errors

We are aware that some of our customers using Sage 100 2018 and older are receiving one or more of the following errors when attempting to email from within Sage 100:

  • "Failed to read beginning of SSL/TLS record"
  • "Failed to read incoming handshake messages"
  • "Failed to establish TLS connection"

Update 1: TLS (Transport Layer Security)

Microsoft® announced the deprecation of Transport Layer Security (TLS) versions 1.0 and 1.1 in Office 365 and Office 365 GCC in January 2020. Microsoft® and Sage recommend that all client-server and browser-server combinations use TLS 1.2 (or a later version) to maintain connection to Office 365 services.

Update 2: SMTP (Simple Mail Transfer Protocol) Deprecation of Basic Authentication

  • Microsoft®  has announced the end of support for Basic Authentication (user and password credentials) for Exchange Web Services (EWS), Exchange Active Sync (EAS), Post office Protocol (POP), Internet Message Access Protocol (IMAP), and Remote PowerShell (RPS) in Exchange Online.
  • Going forward, only Modern Authentication will be supported after October 1, 2022.

How these changes impact you?

  • Sage 100 2019 and higher currently supports TLS 1.2.
  • We are currently exploring the possibility of releasing a fix for our retired version, Sage 100 2018, in order to get customers through the upcoming busy season.
  • Sage 100 customers will need to upgrade to version 2021 or higher by October 1, 2022 in order to not be impacted by the deprecation of Basic Authentication with SMTP.

Note: Other possible causes for SMTP failure/email failure in Sage 100 Paperless Office include:

  • Port blocked by Windows Firewall (or other firewall) resulting in connection time out.
  • Firewall/antivirus anti-spam settings.
  • SSL setting selected for SMTP encryption in Sage 100 Company Maintenance – Email – but TLS is required for connection to Microsoft Office 365 email.

To troubleshoot these possible causes please read this Sage Knowledgebase article.

Please reach out to us if you have any additional questions or concerns.

Best regards,

Sage 100 Team

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