Media technology permeates our social, leisure, and work life, and the ongoing global Covid-19 pandemic has proven that interactive and mobile technologies are not only deeply absorbed in, but also increasingly indispensable to everyday life. Although these technologies are promoted and widely adopted as means to connect people, support everyday activities, mitigate specific problems, or merely make life easier and more enjoyable, they just as often "get in the way" by being perceived as troublesome, counterproductive, or in other ways catalysts of struggles. These specific struggles require our attention and force us to reflect--more or less consciously--on our often-unnoticed relation to media technology. Our aim with this special issue is to shed light on the different encounters and the users' sense-making and reflection within such lived experiences of struggling with technology.