It depends- are you manually entering your HSA contributions made through payroll in the HSA entry in TurboTax? If so, you shouldn't do that as you will be double-counting your contributions. If you have multiple W-2s, yes, all the contributions in box 12, code W are summed together to arrive at your yearly contributions. TurboTax will sum them up for you. If you have multiple jobs, the yearly maximum still applies.