(1) Background: Social evaluation engages neural systems involved in stress and social information processing, with responses potentially depending on valence and evaluator characteristics. We investigated how valence and evaluator sex are reflected in functional connectivity (FC) within a meta-analytically derived stress network in women. (2) Methods: Sixty-three healthy women underwent functional magnetic resonance imaging while receiving praise, criticism, and neutral statements from unfamiliar male and female evaluators. Task-based FC was examined within the stress network. (3) Results: Participants reported less positive affect during criticism and more positive affect during praise, with both effects more pronounced for male than female evaluators. Stress-network FC differed by valence and evaluator sex. Both praise and criticism were associated with greater left insula-–right inferior frontal gyrus FC than neutral statements, while criticism was associated with greater left superior temporal gyrus–right amygdala FC than praise and neutral statements. Furthermore, evaluator sex modulated valence-dependent FC across several FCs involving prefrontal, striatal, medial temporal, thalamic, and posterior midline regions. Post-hoc comparisons revealed evaluator-sex differences in FC during criticism and praise, as well as opposing valence-dependent FC patterns between male and female evaluators. Exploratory analyses showed that associations between FC and self-related positive affect also depended on valence and evaluator sex. (4) Conclusions: Stress-network FC during the perception of praise and criticism delivered by strangers depended on evaluator sex. Importantly, stress-network involvement was not restricted to criticism, indicating that praise may also engage stress-related neural processes depending on social context, particularly when voiced by a male.