ssl issue triggering email.

Question

Hi All

I am using exchange 2016 hybrid environment. I am trying to trigger a test email from PowerShell using onprem relay. i am getting the below error.

Send-MailMessage -SmtpServer mrfa.contoso.com.com -Credential $credential -From 'serviceaccount@contoso.com' -To 'myuser@contoso.com' -Subject 'TEST' -Port 587 -UseSsl

Send-MailMessage : Authentication failed because the remote party has closed the transport stream.
At line:1 char:1

• Send-MailMessage -SmtpServer mrfa.contoso.com.com -Credential $c ...
• ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
• CategoryInfo : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpException
• FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage

I am getting emails when i remove -UseSSl. Experts how do i fix the SSL issue.

Answer 1

@Roger Roger

Mark sure TLS 1.2 is enabled on your server. Here is a related thread: Authentication failed because the remote party has closed the transport stream

Here is a blog which could help you to enable TLS 1.2, choose the suitable one based on your .NET version: Exchange Server TLS guidance Part 2: Enabling TLS 1.2 and Identifying Clients Not Using It

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