By considering the fact that the children from DSMF (double-settlement multicultural families) are under the influence of two different mainstream societies as well as two native speaker parents from each country, this study explored what kind of language learning environments can be provided to them. This study was aimed at sharing insights as to what kind of language barriers the DSMF children may face in the course of learning both languages and finding possible ways to help them overcome these difficulties. In order to suggest several hypothetical scenarios, this study applied some general theories about language development to the documented case of a DSMF child highlighted in Lee’s 2020 study, as a part of employing a theoretical triangulation strategy. The result of the study made it clear that the parents’ life-changing decisions about 1) which parent will be the main-caregiver, 2) how long the child will be staying in each country, and 3) how frequently and in which country the family will reunite may exert an influence upon the quantity and the quality of each language input. Accordingly, a few theoretical propositions were put forward in order to better help DSMF children learn both languages.