Fix Microsoft 365 Not Receiving Emails from WordPress or OpenAI

Open your Microsoft 365 mailbox, navigate to the 'Junk Email' folder, and look for the missing messages from WordPress or OpenAI. If found, right-click the email and select 'Not Junk' to return it to your inbox.

Go to Settings (gear icon) > Mail > Junk email. Under the 'Blocked senders and domains' section, ensure the specific domains (e.g., openai.com) are not accidentally listed.

In the same 'Junk email' settings menu, locate the 'Safe senders and domains' list. Add the specific sending domains or exact email addresses to ensure future messages bypass local junk filters.

Navigate to Settings > Mail > Rules. Carefully review your active rules to guarantee none are configured to automatically delete or move emails containing certain keywords or originating from these senders.

Log into the Exchange Admin Center, navigate to Mail flow > Message trace, and initiate a trace for the affected recipient and sender domains. This will reveal if the email reached the server and where it was dropped.

Access the Microsoft Defender portal and navigate to Email & Collaboration > Review > Quarantine. Check if the system flagged the legitimate emails as spam or phishing, and release them if necessary.

In the Defender portal, go to Policies & rules > Threat policies > Anti-spam. Review the inbound policies to ensure the security thresholds are not overly aggressive against automated third-party mailers.

Under Threat policies, access the Tenant Allow/Block Lists. If necessary, explicitly allow the domains or IP addresses utilized by WordPress and OpenAI to prevent future tenant-wide blocks.