Infants' abilities to orient and regulate are directly linked to self‐regulatory capacity in childhood, which is subsequently associated with indicators of health and well‐being. However, relatively little is known regarding factors affecting early orienting and regulation. The current study evaluated the effects of infant negative affect and household chaos when children were 4 months old and parenting at 6 months of age on subsequent regulatory capacity at 8 months of age in a sample of 179 mother‐infant dyads. The potential moderating role of infant sex was examined in consideration of the viability–vulnerability tradeoff theory, which posits that females may be more susceptible to the impact of stressful environments in early development. Analyses indicated that early household chaos was related to subsequently lower orienting/regulatory abilities at 8 months of age. Additionally, there were significant sex‐by‐negative affectivity and sex‐by‐household chaos interactions, such that boys' regulatory capacity was negatively impacted by early negative affectivity and girls' was adversely affected by household chaos. Findings indicate some support for the viability–vulnerability tradeoff theory. The current study evaluated whether early negative affect and contextual factors impacted infant orienting/regulation at 8 months of age, and whether they influenced boys and girls differently. Results indicate that chaotic household environments negatively impact infants' ability to orient/regulate, and that male and female infants are differently affected by early negative affectivity and household chaos. This study suggests that parents should aim to decrease levels of home chaos to promote optimal regulatory development, and finds some support for the viability‐vulnerability tradeoff theory.