Digital inclusion is increasingly recognized as a key factor in promoting social connectedness and reducing isolation among older adults. In line with this, the United Nations highlights the importance of expanding access to digital technologies in later life. This study investigates the role of voice assistants (specifically Amazon’s Alexa) in supporting digital inclusion and fostering intergenerational connections among older adults. Fifteen participants, aged 60 to 89, engaged in a 60-day in-home trial using Alexa. Although most had little to no prior experience with voice-based technologies, they were encouraged to perform everyday tasks such as sending messages, listening to music, retrieving information online, and setting reminders. Throughout the study, 15 structured tests were applied to assess usage patterns, adaptability, and perceived value. Results show that participants were willing and able to engage with voice technology, reporting increased confidence, autonomy, and a sense of digital belonging. Moreover, by performing tasks commonly associated with younger generations, participants expressed a feeling of connection across age groups. The findings suggest that voice assistants, due to their intuitive and low-barrier interface, can play a meaningful role in bridging the digital divide and strengthening intergenerational engagement.