Major advances have been made in understanding language learning strategies (LLS). However, rapid changes in human interaction induced by the internet and web 2.0 warrant a re-assessment of LLS in today’s context, especially vis-à-vis digital nativeness. Therefore, a large-scale quantitative investigation involving 891 college students was conducted. Their LLS use patterns and frequency and their level of digital fluency were examined using two instruments: Oxford’s Strategy Inventory for Language Learning (SILL) and Teo’s Digital Natives Assessment Scale (DNAS). The participants reported moderate usage of all the strategies described in SILL. However, they reported using specific SILL categories (compensation, memory, and metacognitive) more frequently than others (social, cognitive, and affective). Participants with different levels of digital fluency showed significant variations in the frequency of use of LLS. Additionally, compared to previous generations, these modern participants adopted different usage patterns.