This study aimed to (1) examine relations between youth adjustment and three sets of predictors: parental illness/disability characteristics, caregiving, and parent–child attachment, and (2) explore differences on these variables between youths of parental physical illness/disability and youths of parental mental illness. Eighty-one youths between 10 and 25 years of a parent with a physical illness/disability (35%) or a mental illness (43%) completed a series of self-report measures assessing perceived characteristics of the parent's illness/disability, caregiving experiences, and adjustment outcomes. Results revealed a set of predictors of poorer youth adjustment: Gradual illness/disability onset, being male, isolation, lower perceived maturity, and less choice in caregiving. Youths of parental mental illness differed from youths of parental physical illness/disability on emotional distress (worry and discomfort) dimensions of caregiving. Youth–parent attachment security was associated with youth caregiving and there was a trend for attachment to vary according to parental illness/disability type. Findings highlight young caregiving as an important target for service and policy planning.