This study evaluated the effectiveness of contextualizing Technical Drafting with Computer-Aided Design (CAD) — specifically AutoCAD Version 2013 — in enhancing student learning outcomes at Cebu Technological University – San Francisco Campus (CTU-SF). Employing a quantitative-descriptive research design, the study involved 247 second-year Bachelor of Industrial Technology students enrolled in Computer Technology and Electronics Technology programs during Academic Year 2025–2026. Data were gathered using an adapted survey questionnaire disseminated through Google Forms and analyzed using frequency, percentage, weighted mean, Pearson Product-Moment Correlation, t-test, and one-way ANOVA. Results indicated a moderate level of student learning across five CAD competencies: system features, design, usability, accuracy in creating technical drawings, and proper use of tools and commands. Students' perception of AutoCAD was likewise moderate, yet a significant positive relationship (r = 0.779, p = 0.002) was established between learning levels and perceptions. Significant differences in learning outcomes were found based on frequency of CAD practice, while age and sex showed no significant effect. Based on these findings, a contextualized and outcomes-based Learning Guide structured into six progressive modules was developed to bridge classroom instruction and professional industry practice.