Sage100 2018 or older unable to email using office365

Sage 100 2018 or Older cannot send emails via Office 365 or need to try it multiple times

Issue

You are trying to send emails from Sage 100 2018 or older version using Office 365 SMTP Server and are unable to send emails, or you have to retry the email a few times for it to go through. When you look at the "Error During Electronic Deliver" you see the below messages

Connection closed by server.
Failed to read beginning of SSL/TLS record.
Failed to read incoming handshake messages. (1)
Client handshake failed.
Failed to establish TLS connection.

Why is this happening

When sending an email via office 365 from sage 100 or older, it uses TLS 1.0 or 1.1, which is the encryption used for connection between Sage 100 and Office 365. Microsoft has recently changed the encryption to default 1.2, and are slowly deprecating the use of the less secure TLS 1.0 and TLS 1.1.

Sage 100 2018 and older versions do not support TLS 1.2.

Workaround

There are three workarounds

  1. Consider upgrading to a current version of Sage 100 . This is as per the solution ID: 106485 from sage
  2. Temporarily use an SMTP service like smtp2go.com. Please use this at your own risk. Once setup, you would reconfigure Sage 100 to use the SMTP2Go configuration.
  3. You can enable Legacy protocols on Office 365 tenant until the Sage is upgraded using Powershell via the Online Exchange Management, by doing the following:
    1. Run the following Powershell command: Set-TransportConfig -AllowLegacyTLSClients $True
    2. If smtp server smtp.office365.com does not work try using legacy-smtp.office365.com
Solutions 2 and 3 are provided as courtesy. gotomyerp is not responsible for any interruption to your mail service due to any misconfiguration on your Exchange tenant. If you are unsure how to do this properly, please consult with an IT Professional to assist.


More Information

  2. More information on workaround is listed here