A narrative tipping point leading to the abolition of capital punishment will come from specific events and broader trends that move public opinion and the accompanying legal systems away from the justification for death penalties. Through Singapore’s independent digital journalist Kirsten Han’s reflection on her reportage and advocacy for the abolition of capital punishment in the republic, this paper seeks to highlight the role of digital advocacy in pushing for the narrative tipping point on the death penalty online. Against global trends of abolition, retentionist cultures on capital punishment remain resilient, particularly in countries that claim strong domestic support for authoritarian populist narratives of being “tough on crime.” Institutionally sustained and discursively binarized as “Asian values” against rights-based Western individualism and continuously reiterated by national leaders, Singapore’s policy on capital punishment is termed muscular retentionism. Contending with this dominance in cyberspace is Han’s affective emphasis on death row inmates facing imminent execution, particularly those condemned to death for drug trafficking. Using a partially autobiographical approach as the second author of this paper, she illustrates her experiences as a woman activist in Singapore, journeying with these inmates and documenting their experiences as part of the broader effort to move toward the narrative tipping point. Positioned against the largely impersonalized and instrumental justification of the traditional retentionist position established in the pre-Internet decades is Han’s rights-based emphasis on the sanctity of life. Receiving little attention in the republic’s mainstream media, cyberspace has oxygenated this perspective. Aside from facing legal and police scrutiny for her involvement in abolitionist campaigns, Han has also been subjected to misogynist ad-hominem attacks online from supporters of retention. Kirsten Han’s digital advocacy journalism poignantly sharpens the existing feminist critique in Singapore of the carceral regime with a more intersectional approach toward expanding the scope of the discussion to that of predominately male death row inmates. Her emphasis comes from the notion of difference feminism in considering the structural inequalities and power dynamics that render the more socially disadvantaged vulnerable to the regimes of punishment. Aside from being openly singled out and chastised by the state, it may remain difficult to determine the public impact of Han’s journalistic work. Nonetheless, through amplifying the otherwise invisible emotional states and voices of death row inmates and their families as individuals, she exposes the human cost in the regime of capital punishment and in the process inches Singapore toward the narrative tipping point.