The focus of this master’s thesis is on family-run small and medium enterprises and their adoption to information systems. The motivation for this research is to understand the family businesses’ challenges related to technology adoption, so that the level of hesitancy many family SMEs are having with the process can be understood and minimised. In addition, by understanding family businesses’ challenges related to information systems adoption, we can understand if they are different entities from non-family SMEs, and whether or not they require specialised guidance and support. To achieve the objectives of the master’s thesis, a qualitative multiple case study approach was undertaken involving three family SMEs who were interviewed using a semi-structured interview guide which was inspired by the four key contexts of the Decision-Maker-Technology-Organisation-Environment model. Upon the completion of a thematic analysis of the data, a total of seven themes emerged which can be used to help describe and answer how family SMEs perceive information systems adoption and the challenges. From the findings it was discovered that family SMEs usually hire relatives when they have a vacancy instead of hiring an individual who is more qualified and experienced in the job role, as it is easier and convenient to make use of the trusting relations between family members. In the majority of cases, this means that the family SMEs usually have a limited level of skills including IT knowledge and to overcome this issue they seek help from sources outside of their organisation. The results of this master’s thesis research show that Family SMEs usually have a positive outlook when it comes to carrying out the information systems adoption process,but despite this, hesitancy to initiate the information systems adoption process arose from the lack of awareness of the technology and its possibilities as well as the high cost of funding and setting up the information system.