Artificial intelligence virtual health assistants are a promising emerging technology. This study is a process evaluation of a 12-week pilot physical activity and diet program delivered by virtual assistant “Paola”. This single-arm repeated measures study (n = 28, aged 45–75 years) was evaluated on technical performance (accuracy of conversational exchanges), engagement (number of weekly check-ins completed), adherence (percentage of step goal and recommended food servings), and user feedback. Paola correctly asked scripted questions and responded to participants during the check-ins 97% and 96% of the time, respectively, but correctly responded to spontaneous exchanges only 21% of the time. Participants completed 63% of weekly check-ins and conducted a total of 3648 exchanges. Mean dietary adherence was 91% and was lowest for discretionary foods, grains, red meat, and vegetables. Participants met their step goal 59% of the time. Participants enjoyed the program and found Paola useful during check-ins but not for spontaneous exchanges. More in-depth knowledge, personalized advice and spontaneity were identified as important improvements. Virtual health assistants should ensure an adequate knowledge base and ability to recognize intents and entities, include personality and spontaneity, and provide ongoing technical troubleshooting of the virtual assistant to ensure the assistant remains effective.