Sheltered workshops provide a major arrangement for the employment of people with disabilities in Germany. As a special system, they offer a segregated employment relationship that does not include participation in the general labour market and must be distinguished from supported employment. At the same time, they are part of integration assistance and are therefore also intended to promote participation in the general labour market. Despite this mandate, transitions of people with disabilities from workshops to employment on the general labour market in Germany have remained the exception for decades. Against this backdrop, the article provides insights into the results of embedded research in the facilities of a welfare organisation. The aim was to gain a better understanding of the factors that promote and hinder successful integration assistance in terms of transitions to the labour market in workshops and other facilities run by this welfare organisation and to draw conclusions for the entire system. To this end, five researchers took part in daily practice in the facilities on a total of 25 full working days and documented their observations. The content analysis of the observation protocols offers insights into the perspectives of people with disabilities on the one hand and pedagogical staff on the other on the general labour market. On this basis, recommendations for action are developed and presented in the article. These recommendations will also be used as a basis to determine suitable application scenarios of an AI-based solution that aims support self-determined vocational orientation.