The use of voice assistants (e.g., Amazon Alexa, Google Home) is being widely advocated as part of supporting people living with dementia at home. The development of this technology is largely driven by industry, and there is little research to determine how family carers and professionals use voice assistants with people with dementia. This paper presents the findings from further analysis of data from two studies: Study 1—a qualitative study that aimed to explore the views and expectations of family carers and professionals who use voice assistants to support people with a cognitive impairment at home, and Study 2—a qualitative enquiry aiming to identify the views and barriers on using voice assistants by family carers of people with dementia and professionals, together with a pilot case study evaluating a prototype that addresses barriers identified during the enquiry, entitled IntraVox. Based on processing of smart home sensor data, IntraVox uses a personalised human voice to send prompts and reminders to end-users to conduct daily life activities and to activate smart home processes using voice assistants. The results of the qualitative studies indicate that family carers and professionals use voice assistants in their caring role for home automation, skills maintenance and development, prompts and reminders, behaviour and environment monitoring, and for leisure and social interaction support. The findings also show that family carers and professionals have specific challenges that need to be overcome for them to realise the benefits that may be gained through the use of voice assistants within technology enabled care. The pilot case study also provided a useful demonstration that interoperability can be achieved to enable exchanges between IntraVox and voice assistants, with the aim of providing customised and personalised technological solutions that address some of the barriers that people with dementia and their carers face in the use of this technology.