This case study describes a codesign research project that uses cultural probes and draws on ethnographic surrealism. My rationale for this approach was to move participation in codesign from coercion to collaboration in exploring research possibilities and limitations in codesigning alternative imaginaries in an increasingly data-rich world. My methodological experimentation began in 2010 with the development of codesign workshops that engaged end-users in critical and creative explorations of data in everyday life. The shift to an ethnographic surrealism approach in the workshop design was a response to what I saw as the need to explore and collect data on sensitive and under-researched topics, such as women’s experiences of aging and sexism. In 2018, I devised a series of codesign research workshops that aimed to test the ethnographic surrealism research approach and identify key issues and themes on menopause in the workplace with women who had experienced its symptoms. My approach was grounded in the conviction that the outcomes needed to reframe menopause as a rite of passage rather than a taboo that was either concealed, ignored, trivialized, or medicalized at work. COVID-19 lockdowns in Australia, however, meant shifting the research workshops from face-to-face to online mode with cultural probes. This case study describes the specific methodological and practical challenges this shift presented for researchers in the context of hybrid online-face-to-face workshops, codesigning with cultural probes, and creating a safe, collaborative space in which to co-produce knowledge about women’s experiences of menopause at work with the aim of transforming workplace policies.