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For this answer, I'm going to assume your employer paid for your HSA once you started working there in April (paid meaning with or without any possible pre-tax deductions that may have been deducted from your gross wages, which if you had any, your employer would have reported them in the W2, box 12, code W). Furthermore, I'll assume you are a single filer. In this case, you'll be picking option #3 since you had different plan types at different times of the year: Jan. thru Mar. you were on some family plan paid by your parents, and starting in April, you were on an HSA/HDHP plan paid by your employer. On the next screen where it says "let's maximize your contribution limit," you check off "none" for months Jan. thru Mar., and leave "self only" checked for all the other months. That's about it! If my assumptions were wrong, add another post and we'll go from there.