In the UK, ‘Ageing in Place’ has exerted pivotal influences on policies and practices concerning older people and their well-being. It is built on a premise that older people can live an autonomous and independent life at their homes. Nonetheless, previous studies have found that it is not without negative impacts. Older people could potentially become isolated and experience loneliness. Digital technology has been increasingly recognised as an important instrument to alleviate such adverse feelings, and furthermore, to facilitate an active and healthy later life. With 36% older people over 65 reported to be offline and more to be limited users, it is imperative to understand what the barriers are. This study collaborates with a leading digital inclusion charity in the UK and analyses two survey datasets of digital skills learners collected between 2015 and 2017 (n=1217, older people n=124; and n=1153, older people=275). Chi2 test, Kruskal-Wallis test and binary logistic regression were used for data analysis. Findings suggest that older learners (aged 65+) have gained beneficial outcomes from the Internet, ranging from general feeling such as self-confidence to the management of their daily life in health, housing, and finance. However, these outcomes are not safeguarded, but rather fluid, as results suggest that barriers can emerge in aspects from motivation, access, and skills to a meaningful engagement of the Internet. Policy makers and service providers should ensure a sustained access to and use of digital technologies for older people ageing in place.