Resolving Microsoft Outlook S3140 errors for transactional emails requires a comprehensive approach that combines technical correctness, proactive monitoring, strategic communication with Microsoft, and adherence to best practices. Key areas include building and maintaining a positive sender reputation through consistent IP warming, ensuring proper email authentication (SPF, DKIM, DMARC), configuring and maintaining email infrastructure correctly, monitoring feedback loops and complaint rates, and avoiding spam triggers in email content. Furthermore, persistence and clear communication are crucial when dealing with Microsoft support, often requiring escalation and multiple attempts. Utilizing Microsoft's SNDS and JMRP programs is essential for monitoring IP reputation and spam complaints, while DMARC reporting helps identify and fix authentication issues.