To implement effective diversion programs and determine for a well-suited intervention strategy, ascertaining who, among the adjudicated youth, is more likely to involve in multiple offending, rather than desisting after an initial delinquent behavior, is of great significance. The overall objective of this study, therefore, is to contribute to the existing knowledge on assessing the risks for multiple offending during juvenile adjudication processes. In this regard, this study examined the predicting powers of several individual-level and family-level risk factors on multiple offending during adolescence, based on a data set derived from court-ordered social examination reports (SERs) on 400 adjudicated youth in Turkey. Two binomial regression models were implemented to test the predictor values of various risk factors from these two domains. Results indicated the following as significant predictors of multiple offending among the subjects: younger age of onset in delinquency, dropping out of school, having delinquent/drug abusing (risky) friends, being not able to share problems with the family, increased number of siblings, and having a domestically migrated family. Conclusively, these findings were compared with the existing literature, and the policy implications and recommendations for future research were discussed.