The present study sought to underline the need for expanded transitioning college programming to the 2nd year by examining dysfunctional career thoughts among college students with learning disabilities (LDs). Multivariate analysis of variance (MANOVA) was used to examine the mean differences between 93 college sophomores and seniors with LD on the three subscales of the Career Thoughts Inventory (CTI). Findings from the MANOVA showed significant mean differences among groups. Follow-up analysis found that sophomores showed significantly higher dysfunctional career thoughts than seniors. Seniors displayed substantially lower mean scores on the CTI subscales than sophomores. Findings support the need to extend transition programming that includes addressing students' dysfunctional career thoughts beyond the 1st year to help ease college transition difficulties and thus promote persistence and retention of students with LD. Research and practice implications are presented for career scholars and practitioners working with college students with LD.