Abstract-Security engineering is considered to be a challenging task in order to build systems that remain dependable in the face of malice, error, or mischance. Recent approaches propose the application of domain specific modeling languages (DSMLs) in order to facilitate security engineering activities. To support the development and application of adequate DSMLs, agile approaches and frameworks to provide appropriate tooling are needed. In this paper, we document our experiences developing modeling tools for two different DSMLs in the domain of security engineering. We sketch the language and implementation requirements for our modeling tools, design and implementation considerations, and report on pitfalls and remaining issues with regard to the development of modeling tools based on our experiences.