The United Nations Rules for the Treatment of Women Prisoners and Non-Custodial Measures for Women Offenders (the Bangkok Rules) advocate for the increased use of non-custodial measures alongside women-wise criminal justice programs, policies, and practices. In Thailand, since the Bangkok Rules were adopted, there has been increased attention paid to implementing affirmative action to counterbalance the gender discrimination women face behind prison walls. However, there is a sparsity of knowledge and consideration of women’s non-custodial involvement, in Thailand and worldwide. In this paper, we present findings from research exploring women’s pathways to and experiences of electronically monitored (EM) parole in Thailand. We found that women’s criminalisation trajectories were facilitated by a configuration of multifaceted, commonly interconnected, vulnerabilities and harms. While EM parole should, according to governmental rhetoric, be rehabilitative and supportive of reintegration through ‘the treatment of offenders in accordance with international norms and standards’ in practice, women’s needs were barely recognised, let alone met. Instead, rather than supporting women, EM parole was, in many ways, setting them up to fail.