Microsoft 365 features that help users manage their subscriptions, account settings, and billing information.
Hi Taylor Davey,
To configure Oracle applications to send automated emails using Office 365's SMTP relay, the command openssl s_client -connect smtp.office365.com:587 -starttls smtp is useful for testing the connection to the Office 365 SMTP server over TLS.
Here’s the general process for setting up SMTP relay for Oracle auto mailers with Office 365:
- Establishing a Secure Connection: Run the command:
This connects to the Office 365 SMTP server using the STARTTLS protocol, which ensures your connection is secured before sending any email data. If successful, you’ll see details of the SSL certificate used bybashCopy codeopenssl s_client -connect smtp.office365.com:587 -starttls smtpsmtp.office365.com. - Configure Oracle Workflow Mailer: Within Oracle Workflow Mailer, you need to configure the mailer to use the Office 365 SMTP server:
- SMTP Host:
smtp.office365.com - SMTP Port:
587(for STARTTLS) - Encryption:
STARTTLS(this ensures secure communication) - SMTP Authentication: Yes, use your Office 365 credentials (e.g., a dedicated service account)
- SMTP Host:
- TLS/SSL Certificates: Office 365 uses public root certificates (such as DigiCert), which are trusted by most systems. If your system does not recognize these by default, you might need to ensure the root and intermediate certificates are installed on your Oracle server. In most cases, however, this is not necessary for cloud-based services like Office 365.
- SMTP Relay Settings: You will also need to ensure that your Office 365 tenant is configured to allow SMTP relay. You may use Direct Send, SMTP client submission, or configure connectors in Exchange Online for more advanced setups depending on your use case.
Once you’ve established the connection, the Oracle application can relay emails through Office 365 securely. Let me know if you need help with any specific part of the process!