So I've seen plenty of answers and discussion to the question, can you deduct interview and application expenses related to getting into a residency program and going directly from dental school to the residency program? These are not deductible. However, I have been working as a general dentist for 3 years and got into an ortho program starting this summer. Does anyone know if these application and interview expenses are tax deductible if I'm working as a general dentist and will continue to work as a dentist while in the program when I moonlight? I already have this job lined up. In my view, this is no different than any other CE that a dentist would take. It's obviously more time consuming, but if I continue to work as a dentist even just a few days a month, then this would just be similar to any other CE. I've talked to several different CPA's and the consensus answer is, they don't really know for sure. They say I have a legitimate argument and could likely avoid any penalties due to the argument, if audited and found to be wrong, but would just have to pay the interest. Does anyone know for sure?