Technology continually changes day-to-day interactions, and emergent bilingual learners often multitask, using several digital tools, at times simultaneously, to communicate and learn. Students may text, post on social media, and listen to music as they complete their work. Studies have examined the affordances of technology for language learning, both inside and outside of traditional classroom settings. However, as we seek to better understand how teachers can incorporate students' experiences and interests in academic settings, more research is needed on the nuanced ways that students leverage multiple digital tools as they multitask, or quickly alternate between technologies. This ethnographic study focuses on two high school classes of English to speakers of other languages in the United States. Through the lens of sociocultural theory, we examine how emergent bilingual students multitask with digital tools and how teachers facilitate technology use. Findings reveal that although teachers actively and explicitly approved specific assignments and digital tools that would lead to accomplishing daily language and content objectives, students also purposefully selected other digital tools that would help them co-construct knowledge with peers, and they often switched between various websites across multiple devices to examine content that was closely related to their interests and lived experiences. Evidence from previous studies supports that multitasking can be harmful to learning, but this study found that multitasking can also mediate learning, especially self-directed learning, which has important implications for how teachers implement digital tools in the classroom.