  `Smart cities', urban development projects that design computational systems
and sensory technology to monitor activity and regulate energy consumption and
resource distribution, are a frontier for the prospective deployment of ICTs
for sustainability. Often reduced to technological problems of optimization,
these projects have implications far beyond narrow environmental and
consumptive frames of sustainability. Studying them requires frameworks that
support us in examining technological and environmental sustainability
dimensions jointly with social justice perspectives. This paper uses Critical
Systems Heuristics (CSH) to examine the design of Sidewalk Toronto, an ongoing
smart city development. We explore how the professed values guiding the project
are contentiously enacted, and we argue that key stakeholders and beneficiaries
in the planning process significantly constrain the emancipatory and
transformative potential of the project by marginalizing the role of residents
in determining project purposes. This analysis contributes an example that
illustrates the relevance of critical systems thinking in ICT4S and offers CSH
as a conceptual frame that supports critical reflection on the tensions between
the visions and realities of `sustainable' ways of organizing human life.
