Despite the general consensus regarding the implementation of self-report measures in the training monitoring, there is a lack of research about their applicability and comprehensibility among developing athletes. However, this target group needs special considerations to manage the increasing training demands while maintaining health and performance. This study deals with challenges of applying recovery-stress questionnaires which were validated with adult populations among developing athletes and presents a possible approach to enhance their applicability. In two phases, the Acute Recovery and Stress Scale (ARSS), a 32-adjective list covering eight scales, and the 8-item derived version, the Short Recovery and Stress Scale (SRSS) were answered by 1052 athletes between 10 and 16 years. Phase 1 included 302 14- to 16-year-old athletes who used the original questionnaires with the additional option to mark “I don’t understand,” while modified versions with additional explanations (phase 2) were applied to 438 adolescents (14.7 ± 0.6 years) and 312 child athletes (11.8 ± 1.1 years). Data of the original validation sample (n = 442) were reanalyzed to examine measurement invariance between adults and adolescents. The results showed comparable psychometric properties to the validation sample (e.g., rit > 0.30) and acceptable fit indices via confirmatory factor analyses (CFA), although more difficulties and limitations were present within the younger groups (e.g., Cronbach’s α between 0.50 and 0.87), especially among 10- and 11-year-olds. The original as well as the modified SRSS, on the other hand, indicated good applicability (Cronbach’s α between 0.72 and 0.80). Multigroup CFA revealed measurement invariance of the original ARSS among adults and adolescents and of the modified ARSS among adolescents and children. Overall, the present study confirmed the assumption that questionnaires designed by and for adults cannot be directly transferred to younger athletes. The peculiarities and differences in the cognitive and affective development of each age group need to be considered. Future research needs to identify a cut-off age to start the proper use of psychometric tools, especially for state-oriented assessments for routine application in training monitoring. Further modifications and long-term investigations are necessary to implement psychometric monitoring in high-performance environments within youth sport.