The Master thesis examined the case of designing for meaningful interventions for the international homeless in the context of Copenhagen, wherein complex system barriers influence the practice. The case has been developed with the support of multiple organizations actively engaged in the system through a co-creative approach. The complexity of addressing homelessness and vulnerability at large in the design process called for multiple and multilayered roles and approaches for the designer. Those focused on building trust, and the importance of involving local actors, such as organizations within the field or/and social workers in the process, making sure that reflexivity of the process was present at every stage. An additional layer of the designer as an activist was pointed, as to influence the system, one has to take a stand in making and contributing to a change. Lastly, together with actors from the system, guidelines for designing meaningful interventions have been co-designed with the aim of improving social inclusion, by establishing a better relationship among the international homeless and society. The guidelines can be treated as a setting stone for further development, in order to serve the organizations engaged in the cause, as well as designers and activists having a stake in the system.