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It also used to be that if you entered a W-2 with HSA contributions inbox 12, the program would go right to the qualifying insurance questions before you left the W-2 interview. Entering the code W immediately triggered the HSA questions.  If you bailed out on the W-2 interview after entering the basic numbers, and didn’t finish the rest of the interview steps, you might’ve missed the program trigger for these questions. You can trigger the HSA questions either through the 1099-SA section on the income page or the HSA interview under medical expenses on the deduction page.