Road congestion, air pollution and sustainability are increasingly important in major cities. We look to understand how last-mile deliveries in the parcel sector are impacting our roads. Using formative field work and quantitative analysis of consignment manifests and location data, we identify how the effectiveness of life-style couriers is contributing to both environmental and non-environmental externalities. This paper presents an analysis of delivery performances and practices in last-mile logistics in central London, quantifying the impacts differing levels of experience have on overall round efficiency. We identify eleven key opportunities for technological support for last-mile parcel deliveries that could contribute to both driver effectiveness and sustainability. We finish by examining how HCI can lead to improved environmental and social justice by re-considering and realizing future collaborative visions in last-mile logistics.