This study takes a transnational and collaborative approach to explore how Pacific Island educators are using web 2.0 technology to enhance instruction and facilitate culturally sustaining learning opportunities for emergent bilingual and multilingual students. It is also an analysis of the digital divide for young adolescent users due to linguistic, economic, and geographic barriers. Two middle level education vignettes are presented--one from American Samoa and one from Hawai'i. First, we explore the areas of technology use, collaborative learning, and culturally sustaining education within our unique Pacific contexts. Each vignette consists of an overview of the technology usage within our Pacific contexts, connections to "The Successful Middle School: This We Believe," results, and next steps. This study caters to educators working with multilingual and multicultural populations and contributes to the knowledge base of culturally sustaining pedagogy in middle level online learning environments.