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PrabakaranNagarajan's avatar
PrabakaranNagarajan
Copper Contributor
Aug 19, 2025

Exchange Server 2019 SMTP Error: "Does not support secure connection" on Port 587 with SSL

When attempting to send emails using port 587 with SSL (-usessl), I receive an error stating that the server "does not support secure connection" or that it "does not support the connection encryption type you have specified." Mail sending fails every time SSL is enabled. If I use the unencrypted connection, the mail sends successfully (though this is not recommended for security).

Configuration details:

  • SMTP port: 587
  • Encryption: SSL/TLS (using -usessl parameter)
  • Valid certificate is installed and assigned to SMTP service
  • Client/server both support TLS 1.2
  • Error messages:
    • "Your server does not support the connection encryption type you have specified. 

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