This chapter focuses on utilizing artificial intelligence (AI) digital personal assistants (also known as smart speakers) as a tool to improve English language skills by introducing three case studies. AI smart speakers can be experienced efficiently and smoothly, enhancing the construction of broader learning environments and viewpoints (Kepuska & Bohouta, 2018) and promoting the personalization, contextualization, and socialization of language learning. AI, mobile devices, and social media are the key components of the next generation of this novel wave of educational instruction. AI and mobile technologies have transformed learning methodologies such as blended learning (BL), which combines traditional face-to-face classroom methods with computer-mediated activities, resulting in a more integrated approach to language learning (Obari & Lambacher, 2014). After a brief introduction of artificial intelligence, the basic features of personal assistants/smart speakers, with specific examples of their application in educational and L2 learning environments, are introduced before presenting the key results of three case studies. The primary purpose of the first case study was to ascertain the effectiveness of the smart speakers Google Home Mini and Amazon Alexa within a BL program in improving the English proficiency of Japanese EFL students. The focus of case studies 2 and 3 was on improving English proficiency, particularly presentation skills, and 21st-century learning skills, which promoted both socialization and contextualization by focusing on developing the intercultural awareness of Japanese EFL students. The participants of all three studies were Japanese undergraduates from a private university in Tokyo, Japan. Pretest and posttest TOEIC scores were used to assess the overall effectiveness of the BL-learning program in both case studies. TOEIC score gains indicated the training program incorporating the AI speakers improved the students’ English skills. Moreover, post-training surveys revealed students were impressed with the AI speakers as a tool for language learning, which also impacted their perspectives on studying English and provided contextualization and socialization to their learning through the interactive and meaningful context of the training.