With the growing concern for the health of ageing populations, much research continues to look at the impact of cognitive training, particularly in relation to cognitive decline. We sought to use novel techniques, including augmented reality and portable neurotechnology, to evaluate the impact of a dynamically adjusting cognitive training programme, in comparison to a statically challenging alternative. Before and after an 8-week training period, and at a 5-week follow-up, we used portable functional Near Infrared Spectroscopy to examine mental workload in a mixed battery of cognitive and transfer tasks. A recently developed tablet-based task was used to identify changes in cognitive misbinding. Augmented Reality was used to create a supermarket shopping experience, as a more ecologically valid and realistic transfer task relating to an everyday task relating to independence that quickly becomes difficult with cognitive decline. The analyses showed a decreased mental workload within the dorsolateral prefrontal cortex and that participants considerably increased their performance in the trained task. Some results were maintained at the 5-week follow-up assessment. In terms of transfer, we observed reliable group differences immediately after training completion, which were mainly driven by distinct conditions. Some behavioural memory gains were maintained during the follow-up. The use of novel technologies brought new insights into the effects produced by the dynamic computerised cognitive training programme, which has potential future applications in cognitive decline screening and prevention.