This qualitative study investigates the experiences of digital immigrant teachers—those who adopted technology later in life—in teaching students with Special Educational Needs (SEN) using digital tools. The significance lies in understanding how these educators navigate the complex demands of inclusive digital education, especially as technology becomes integral to modern pedagogy. Grounded in a phenomenological framework, the research involved semi-structured interviews with 12 teachers from Kuala Lumpur and Selangor, Malaysia, each with over five years of SEN teaching experience. Thematic analysis revealed five major themes: adaptation to technology, perceived impact on student learning, barriers to integration, coping strategies, and emotional responses. Findings indicate that while initial encounters with digital tools were marked by resistance and low digital fluency, many teachers gradually transitioned into more confident and innovative users through peer mentorship, self-directed learning, and targeted professional development. Participants noted that assistive technologies, such as text-to-speech software and adaptive apps, enhanced accessibility and engagement for SEN students. However, challenges including inadequate training, time constraints, and classroom management complexities persisted. The study concludes that digital immigrant teachers, despite their initial struggles, can become effective facilitators of inclusive digital education when supported by context-sensitive training and collaborative school cultures. Their emotional resilience and pedagogical expertise are valuable assets that, when combined with digital competence, can significantly improve SEN learning outcomes. This research highlights the need for tailored professional development and intergenerational mentorship to bridge the digital divide and promote equity in special education settings.