This follow-up study investigated the associations of childhood learning disabilities (LDs) with adult-age anxiety, depression, and unemployment. Psychosocial problems in childhood and psychiatric diagnoses and lack of education in adolescence were studied as potential mediators, and gender and mother’s education as potential moderators of these associations. Data on childhood clinical neuropsychological assessments and lifelong register data on individuals with childhood LD (n = 430; 301 [70%] males; 20–39 years of age) and matched controls (n = 2,149) were applied. Mediation analyses were performed using structural equation modeling. Childhood LDs exerted a significant, but relatively small effect on psychiatric diagnoses in adolescence, which predicted adult-age depression and anxiety. LDs were related to unemployment both directly and via psychiatric diagnoses in adolescence. Examination of differences in the effects on adult-age outcomes of subtypes of LDs revealed mathematical disability to be more strongly associated with psychosocial problems in childhood and psychiatric problems in adolescence and adulthood than reading disability. Our findings show that LD has small and mostly indirect effects on the risk for later well-being problems. The findings emphasize the importance of adolescence in predicting adult-age psychiatric and employment problems and call for more holistic support for individuals with LDs.