unable to send emails from application

Roger Roger 4,951 Reputation points
2021-12-02T04:44:01.07+00:00

Hi All

I am using exchange 2016 Hybrid Environment, I am using Anonymous relay and i want to go with authenticated relay.
i have created a user account in onprem Active Directory lets say appuser@Company portal .com and then i have created remote mailbox from exchange onprem and i am using it in application.
on one of the server i have selected exchange onprem relay and i am using below settings.

SMTP Server HostName: myrelay.onprem.contoso.com
SMTP Server Port: 587
Use TLS Security: False
Use SSL Security: False
SMTP Server User name: appuser@Company portal .com
Password:
SMTP Authentication Enabled: True

If i disable TLS Security the mailflow works from the application. If it is enabled it doesn't work. Not sure how do i fix this. Please guide me
So Disabling TLS Security and SSL Security recommended?

Microsoft Exchange Online Management
Microsoft Exchange Online Management
Microsoft Exchange Online: A Microsoft email and calendaring hosted service.Management: The act or process of organizing, handling, directing or controlling something.
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Exchange Server Management
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Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
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Accepted answer
  1. KyleXu-MSFT 26,211 Reputation points
    2021-12-03T02:03:49.577+00:00

    @Roger Roger

    Make sure the TLS is enabled on the connector that you used to relay emails. Make sure the device that you used supported TLS and use the same version as Exchange server.

    About the SSL, I would suggest you use command below to check whether the connector is configured correct:

    Send-MailMessage -SmtpServer mail.domain.com -Credential $credential -From 'user1@domain.com' -To 'user2@domain.com' -Subject 'Test email' -Port 587 -UseSsl  
    

    If you could send from the command successfully, if means this issue may related with the tool that you used.

    If you cannot send email from this command successfully, it mean there exist issue with the connector that you used, you could follow this article to check the configuration on your connector.
    Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.


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