The author was dissatisfied with their initial implementation of SMTP listeners, which used a pipe delivery mechanism and required manual configuration changes through editing config files. The solution had weaknesses, including being less than ideal for scalability and having single points of failure. To address these issues, the author chose Postfix as their mail server, which is easy to automate, free, and supports encrypted TLS connections. They also used Lua as a scripting language for the pipe delivery program due to its small size, speed, and ease of use. The migration process involved building tools to migrate existing SMTP credentials configuration to the new SQL-based login scheme and gradually increasing traffic to the new instances with the help of a DNS-based load balancer.