This study evaluated the perspectives and educational needs of Canadian oncology residents with regard to artificial intelligence (AI) in medicine, exploring the influence of factors such as program of choice, gender, and tech literacy on their attitudes towards AI. An ethics-approved survey collected anonymous responses from Canadian oncology residents from December 2022 to July 2023. Comparisons by demographics were made using Chi-square and Mann–Whitney U tests. A total of 57 residents and fellows responded out of an expected 182, with representation from each oncology training program in Canada. Over half of the participants were male (63.2%), with radiation oncology programs being better represented than medical oncology programs (68.4% vs. 31.6%). There was balanced representation across all years of training. Most trainees (73%) were interested in learning more about AI, and many believed the topic should be formally taught during residency (63%), preferably through workshops (79%). Among evaluated factors, tech literacy showed the most impact over AI perspectives, driving a perception shift towards viewing AI as an improvement tool, rather than as a threat to professionals. In conclusion, Canadian oncology residents anticipate AI’s growing influence in medicine but face educational deficiencies. Gender, oncology discipline, and self-reported tech literacy impact attitudes toward AI, highlighting the need for inclusive education.