This research presents homeless beneficiaries' perceptions of fundraising imagery that represent them, and how their perspectives compare to those of charity staff who publish them. This project employed a qualitative study, interviewing a sample of 42 individuals on their opinions about three highly-circulated homeless charity fundraising adverts. Findings conclude that, while both groups agreed fundraising engages stereotypical depictions of street homelessness, beneficiaries specifically called for more representations of hidden homelessness outside symbols of stigmatization. Even if ads presented the homeless experiencing pain during times of need, beneficiaries wanted context that emphasized their dignity and portrayed poverty as impermanent. This research expands upon theoretical applications in the Third Sector through the lens of charity aid and representations of that aid, while also highlighting the role of identity in media publications.