Automated support for the requirements engineering (RE) process is a recognized research area. However, the mainstream practice still relies on word processors and drawing tools rather than the requirements engineering tools (RETs). The aim of this chapter is to validate an evaluation framework for RETs. The validation process concerns an RET acquisition process for concrete organizational needs. An observation of maintaining requirements specification shows the important organizational and environmental characteristics for a proper automated support of RE process. The contribution of this work is twofold: first, the validation of the evaluation framework for RETs according to environmental needs in a specific environment, and second the identification of environmental needs, which emerge from the requirements specification maintenance process.