HSA is usually a no-brainer. Your federal, and possibly state and SSA taxes are not levied on what you put into the SSA. It also grows tax free if you invest it. You can even withdraw for non-medical needs with a relatively minor penalty. Your bigger issue is the high deductible plan that you typically have to choose and whether those premiums and benefits are reasonable. If your deductible is higher than you can afford or if substantial health expenses are likely in the coming year, that should give you pause.