Design probes, an essential research tool during the COVID-19 pandemic, are ancillary "personal" data gathering tools that enable researchers to enter the private world of research participants. This paper compares two case studies of design probes used during the pandemic for radical placemaking in hybrid digital-physical environments: Digital Art Summer School in Northrock, Ireland, with eleven participants, and Chatty Bench Project in Brisbane, Australia, with sixteen participants. The paper further expands on the design methodology of the probes and their deployment during the online radical placemaking projects. From the participant responses to the probes' activities and interviews, both studies demonstrated that the probes fostered placemaking in digital environments during the pandemic. The paper concludes with three lessons on the potential of probes as a critical research instrument to enable creativity, build social capital and create bonds between people and places during uncertain and turbulent times.