Extensive interviews with 60 employed parents of school-age children treated for mental health problems explored work–family fit, flexibility, family support, and work–life strategies in relation to role quality. Role quality was measured as employment and parenting rewards and concerns. Work–family fit was positively related to family flexibility but not work flexibility. Higher flexibility in work and family predicted lower job concerns, and work flexibility and work–family fit were predictors of job rewards. Parental concerns were dependent on flexibility and work–family strategies. Single parents had significantly fewer sources of family support and used fewer work–family strategies than caregivers with partners. Human services providers should collaborate with families by jointly exploring new flexibility and support strategies in work and family domains.