Docker is a virtualization technique heavily used in the industry to build cloud-based systems. In the context of Docker, a system is said to be observable if engineers can get accurate information about its running state in production. In this paper, we present a novel approach, called POBS, to automatically improve the observability of Dockerized Java applications. POBS is based on automated transformations of Docker configuration files. Our approach injects additional modules in the production application, in order to provide better observability. We evaluate POBS by applying it on open-source Java applications which are containerized with Docker. Our key result is that 148/170 (87%) of Docker Java containers can be automatically augmented with better observability.