This study examined if inconsistent bedtime routines are a mechanism through which high levels of parenting stress are related to bedtime resistant behaviors. Bedtime resistant behavior is a common problem in young children. Although previous studies have linked parenting stress to problematic behaviors at bedtime, understanding how and why that may be has been subject to limited empirical investigation. Caregivers (N = 118) of a child age 2–5 were recruited on Amazon’s mechanical turk. There was a significant indirect effect of parenting stress on bedtime resistance through bedtime routines as well as a significant indirect effect of bedtime routines on bedtime resistant behavior through parenting stress. These findings suggest that there is a bidirectional relationship between inconsistent routines and parenting stress. Clinically, these results suggest that implementing a consistent routine at bedtime may improve both parent (less stress) and child (less bedtime resistance) functioning.