One obvious side effect of migrating to a microservices architecture is the need for infrastructure automation. Unfortunately, most automation systems do not take security into consideration, making production deployments orders of magnitude more complex than the initial testbed deployment. The perfect example of this steep increase in deployment difficulty is the creation and management of Public-Key-Infrastructures (PKI). Even though the use of TLS Certificates for service to service communication is known as a best-practice, very few companies actually deploy their systems using mutually-authenticated TLS connections. In this talk I will go over why TLS is the right solution for service to service communication, describe ways to automate the creation and management of your PKI, and present in detail how Docker's swarm orchestration system bootstraps and manages individual node certificates.