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How to Configure Oracle Email Relay with Microsoft 365 SMTP (smtp.office365.com)
Question details
The user needs to configure Oracle applications or Oracle Workflow Mailer to relay automated emails through the Microsoft 365 SMTP infrastructure.
- Product
- Microsoft 365, Oracle
- Device & OS
- not provided
- Scenario
- Setting up automated email delivery from an Oracle application using Microsoft 365 as the SMTP host.
- Observed behavior
- The goal is to successfully test TLS connectivity and establish an authenticated SMTP connection via smtp.office365.com on port 587.
Ensure you have the credentials for a dedicated Microsoft 365 account, and verify that your Oracle server's firewall allows outbound traffic on TCP port 587.
Configure SMTP Auth Client Submission for Oracle Applications
Set up your Oracle application to send emails using Microsoft 365's SMTP AUTH method on port 587 with STARTTLS encryption.
To relay automated emails through Microsoft 365, the Oracle server must authenticate with a valid Microsoft 365 mailbox using SMTP AUTH. It is crucial that your Oracle server trusts the public certificate authority chain, as Microsoft does not issue custom certificates for their SMTP servers.
Open your Oracle server terminal and run the command: `openssl s_client -connect smtp.office365.com:587 -starttls smtp` to verify that the server can successfully reach Microsoft 365 and initiate a TLS handshake.
Ensure that your Oracle application or wallet is configured to trust the public certificate chain for Microsoft 365. Do not generate a custom certificate for the Microsoft-owned hostname.
Log in to the Microsoft 365 admin center and confirm that 'SMTP AUTH' is explicitly enabled for both your tenant and the specific mailbox you intend to use for sending emails.
In your Oracle application or Workflow Mailer configuration, enter the following details: SMTP Host as `smtp.office365.com`, Port as `587`, Encryption as `STARTTLS`, and provide the credentials of the dedicated Microsoft 365 account.
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Frequently Asked Questions
Why is the Oracle connection to smtp.office365.com failing?
Connection failures usually occur because outbound traffic on port 587 is blocked by a firewall, or SMTP AUTH is disabled for the Microsoft 365 tenant or the specific mailbox being used.
Where can I download the SSL certificate for smtp.office365.com?
Microsoft does not issue a downloadable, customer-specific certificate for this hostname. Instead, you must ensure that your Oracle server's wallet or keystore trusts the standard public certificate authority chain that issues certificates for Microsoft 365.
Can I use port 25 instead of 587 for Microsoft 365 SMTP relay?
For SMTP AUTH client submission, Microsoft strictly requires port 587 with STARTTLS encryption. Port 25 is generally reserved for Direct Send or Office 365 SMTP relay methods that do not use SMTP AUTH.
