Live testing is performed in the production environment ideally without causing unacceptable disturbance to the production traffic. Thus, test activities have to be orchestrated properly to avoid test interferences with the production traffic. A test plan is the road map that specifies how the test activities need to be orchestrated. Developing a test plan includes tasks such as test configuration selection/generation, test configuration deployment planning, creating the test runs schedule, choosing strategies to mitigate the risk of test interferences, etc. The manual design of a test plan is tedious and error prone. This task becomes harder especially when the systems are large and complex. In this paper we propose an approach for automating test plans generation. With this approach we aim at reducing the time needed to execute the test plan while maintaining the service disruption at an acceptable level. We illustrate our approach with a case study and discuss its different aspects.