Theory and empirical research in career counseling have acknowledged the critical contribution of social support to career development. However, the specific contribution of significant others’ support (teachers, parents, counselors) on career decision-making difficulties and the role of Web searching information on this latter outcome are still under investigated. To fill these gaps, 1094 grade 12 students from Ontario, Canada, responded to the Social Support Scale, Career Decision-Making Difficulties Questionnaire (CDDQ), and two specific items regarding the frequency of internet use in searching career-related information and the perceived usefulness of searched information. Findings confirmed the negative association between overall support and overall decision-making difficulties. However, unlike teachers’ support, parental and counselors’ support were essential in reducing the CDDQ ten career decision-making difficulties. More importantly, Ontario career counselors’ support shifted toward providing information. Moreover, higher career-related Web search behaviors significantly reduced CDDQ’s Unreliable information score. Implications of these findings are discussed.