In an era when nearly all students are encouraged to attend college, how well do students' plans anticipate their likely attainments and what senior-year information predicts the way attainments fall short of plans? This paper finds that many college-bound youth hold “no-penalty” beliefs that they can attain their plans even if they do poorly in high school, and these beliefs seem to reduce their efforts in high school. Analyses of the 1992 follow-up of the High School and Beyond cohort who were seniors in 1982 find that while students with low grades can attend college, over 80% of college-planning students with low high school grades fail to complete any college degree 10 years later. Multivariate analyses indicate that high school grades strongly predict educational attainment, predict whether students attain their plans, predict plans-attainment for Blacks as well as for Whites, explain much of the lower attainment and disappointed plans of disadvantaged students, and predict less economic payoff to college degrees. Though well-intentioned, “college-for-all” norms may inadvertently encourage no-penalty beliefs, low effort, and unrealistic plans; hurt students' achievement and later attainments; and set students on a course for later disappointment. Policy reforms are suggested.