Self-healing cementitious materials show potential to reduce material consumption, maintenance costs, and environmental impacts within the construction sector. This study explores the feasibility of installing a ductile-porous vascular network in a series of retaining walls under realistic construction conditions, with the objective of both assessing the efficacy of the self-healing system and addressing any constructability issues that may arise. Numerical modelling was performed first to determine a suitable mix design and wall configuration that would promote cracking, so cracks would appear without mechanical intervention. The predicted crack distribution informed the optimal network configuration. Healing and sustainability considerations are discussed, and the benefits of implementing this technology are evaluated. When comparing a single maintenance activity using a vascular network versus manual repair, there is no significant benefit of using a vascular network. However, environmental impacts are substantially reduced when using a vascular network once multiple repair actions are considered.