APEX SMTP Configuration for Office 365 - Cloud MSP Services

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Do you have trouble sending emails using SMTP mail server? Do you require a secured host server for averting sensitive data theft and hacking? Do you want to integrate the impeccable and hassle-free distribution of bulk emails? If the answer to any of these questions is yes! Oracle APEX deployment by Vast Edge enables enterprises to send emails through Microsoft Office 365. Vast Edge integrates an SMTP server for seamless inbound/outbound mail configuration with Microsoft Office 365 while helping enterprises strengthen email resilience through a secure Microsoft 365 backup solution.

Why Vast Edge for APEX SMTP-Office 365 Configuration?

Oracle ATP with APEX provides enterprise-grade performance to quickly develop, migrate, and deploy high-quality applications using secure Oracle APEX migration services and cloud-native deployment strategies. One of the most important requirements for APEX applications is to send email notifications to the application users as well as external partners. Vast Edge's differentiator for APEX SMTP-Office 365 Configuration are:

Faster Implementation

Vast Edge's deployment solutions don't require any programming or specific tools. Our configuration engineers use pre-defined sample connection templates to set up your SMTP configuration in a few minutes while providing remote setup support for any future issue. APEX application.

Flexible Syncing

Vast Edge's deployed solutions allow one-way, two-way, and multi-way connections with top-notch features like disabling unwanted operations, dynamic columns cleanup, data transformation or translation, and custom business logic addition.

Hybrid Cloud Configuration

Vast Edge integrates applications across Microsoft Office 365, SharePoint, Dynamics, Exchange, Azure, Teams, and other enterprise systems using scalable cloud migration tools and hybrid cloud configurations.

Need Help Configuring Oracle APEX SMTP with Office 365?

Vast Edge helps enterprises configure secure SMTP integration, SSL/TLS setup, Office 365 connectivity, certificate imports, and automated email workflows for Oracle APEX environments.

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✔ Remote implementation support
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✔ Secure SMTP configuration
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✔ Faster deployment assistance
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✔ Enterprise-grade troubleshooting

Proper SMTP configuration ensures reliable application notifications, secure email delivery, compliance readiness, and uninterrupted communication for enterprise Oracle APEX applications.

APEX Office 365 SMTP Instance Setting

An SMTP mail server with an email client or software performs the whole email delivery process. Many users face an error notification in apex while sending emails. Here's an expeditious and facile procedure to configure your apex environment for emails through office 365:

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For APEX 5.x on 12.2.x Database, when a given error occurs while endeavoring to configure in APEX Instance setting an email server with SSL/TLS as office 365:
ORA-24263: Certificate of the remote server does not match the target
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Create an SMTP Host Address: smtp.office365.com
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Input SMTP Host Port: 587
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Enter SMTP Authentication Username: cloud@vastedge.com
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Enter SMTP Authentication Password: XXXXXXXXXXXXXX
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Tick to checkbox if you wish to transmute the password for the SMTP authentication username.
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Go for YES to turn on USE SSL/TLS
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If the server still exhibiting the same error the go for the option after the connection is established to turn on USE SSL/TLS
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Enter Default Email from Address: Cloud@vastedge.com
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Adjust maximum emails per workspace: 10000

If the server still exhibiting the same error, then use these steps to reset

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Upgraded to or configured APEX 5.1.4 on a 12.2 database. ( In 12.2 database, while making a secured connection or request via UTL_TCP, UTL_SMTP, and UTL_HTTP, authenticates the digital certificate of the remote server. It will raise the following error if the server address in the CN attribute of the certificate does not match the requested connection or URL)

ORA-24263: remote server certificate doesn't match the target address.

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Apply Patch Exception for Bug 27590117
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Download the patch 27590117 from MOS
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Check the README docs.
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Apply the patch as per the instructions
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Set the APEX instance parameter SMTP_SECURE_HOST to use SNI for the mail server:
ALTER SESSION SET current schema = APEX_050100;
APEX schema.
APEX_INSTANCE_ADMIN.SET_PARAMETER('SMTP_SECURE_HOST', '{server-hostname}');
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Re-test the configuration of your email server sending an email from within APEX.

The request is now processed

Oracle APEX requires certificates to be securely stored in the DB wallet for third-party integrations to function properly while aligning with enterprise backup and disaster recovery best practices. This is done to maintain security to deliver enterprise-grade applications. In order to setup SMTP access in APEX to send emails through office 365, we need to first import the certificates from office 365. The certificate chain can be found here at Office 365 Certificates. Next, you need to set up the SMTP settings as shown in the attached image. And now, you will be able to send emails from APEX through office 365.
Make sure to check use SSLTLS after the connection is established under instance email settings. Also, there should only be one slash in the wallet certificate file path.

FAQ

Frequently asked questions

Q1. What is the SMTP server configuration for Office 365?

To configure Office 365 SMTP, use the host address smtp.office365.com paired with port 587. It requires explicit TLS encryption (STARTTLS) and a valid, fully authenticated Microsoft 365 cloud mailbox username and password to route outbound emails safely.

Q2. How do I configure Oracle APEX to send emails?

Configuration is managed within the APEX Instance Administration under "Internal Workspace Settings." You must navigate to Instance Settings, select Email, and input your SMTP host address, port, authentication credentials, and default "From" address before establishing a secure wallet connection.

Q3. Is SMTP port 25 or 587?

For secure modern application routing, port 587 is the standard industry choice because it utilizes explicit TLS encryption (STARTTLS) for authenticated email delivery. Port 25 is traditionally used for server-to-server relaying and is frequently blocked by cloud ISPs to mitigate spam risks.

Q4. What is the SMTP server address for Office 365?

The official global SMTP server address for all Microsoft Office 365 tenants is smtp.office365.com. This endpoint routes outbound system emails from external platforms like Oracle APEX into the Microsoft cloud ecosystem.

Q5. How do I fix the ORA-24263 certificate error in Oracle APEX with Office 365?

This error occurs in modern Oracle databases because the remote server's digital certificate doesn't match the requested target address. To fix it, apply patch 27590117 from My Oracle Support (MOS) and use the APEX_INSTANCE_ADMIN.SET_PARAMETER procedure to set the SMTP_SECURE_HOST parameter to use SNI (Server Name Indication).

Q6. Do I need to import Office 365 SSL certificates into the Oracle Database Wallet?

Yes. For any secure third-party integration, Oracle APEX requires the entire root and intermediate certificate chain from Microsoft Office 365 to be securely stored in your Oracle DB wallet file path. Without importing these trusted certificates, the database will block outbound UTL_SMTP handshakes.

Q7. Should I check "Use SSL/TLS" immediately or "After connection is established" in APEX mail settings?

For Office 365, you must select the option to turn on SSL/TLS "After the connection is established" (STARTTLS). Setting it to use SSL immediately will result in a connection timeout because port 587 expects an initial unencrypted connection that is immediately upgraded via a command handshake.

Q8. Why is Oracle APEX failing to authenticate with my Office 365 SMTP username?

Authentication failures typically happen if the SMTP Authentication username does not match the "Default Email From Address" set in APEX, or if Microsoft Security Defaults are blocking Basic Authentication. Ensure that "Authenticated SMTP" is explicitly enabled for that specific mailbox within your Microsoft 365 Admin Center.