Developers invest much effort into validating configuration during startup of free/libre and open source software (FLOSS) applications. Nevertheless, hardly any tools exist to validate configuration files to detect misconfigurations earlier. This paper aims at understanding the challenges to provide better tools for configuration validation. We use mixed methodology: (1) We analyzed 2,683 run-time configuration accesses in the source-code of 16 applications comprising 50 million lines of code. (2) We conducted a questionnaire survey with 162 FLOSS contributors completing the survey. We report our experiences about building up a FLOSS community that tackles the issues by unifying configuration validation with an external configuration access specification. We discovered that information necessary for validation is often missing in the applications and FLOSS developers dislike dependencies on external packages for such validations.