This paper presents findings from three participative case studies in the selection of a Remote Assistance application. The needs for a Remote Assistance application were different: vanity project, commercial pressure, COVID-19 imposed travel bans. The case organisations had different motivations, different evaluation approaches and different decision flows. However, none of the organisations followed the formally described approaches of criteria definition, criteria ranking, score calculation and decision. The studies show chaotic and iterative processes which are influenced by participants’ attitudes and humours more than by formal procedures and business-school teachings. The motivations for IT-use appear to influence the decisions more than the (in-)formality of the evaluation process. The paper concludes with a discussion of the findings and proposals for further research.