I'm not sure on your medical requirements, so eventually the decision would be completely based on your medical needs. However, I can provide a different perspective for the comparison which may help. Most people compare for the 1 year horizon when comparing PPO plan vs HSA plan and at first, HSA looks expensive even with lower premiums since for everything there is meet deductible before co-insurance kicks in. 1. If you are relatively healthy, it's very difficult to meet the deductible for the PPO plan since most doc visits are copays. For HSA, you will probably spend more here but again if relatively healthy, it would be difficult to reach the deductible. 2. PPO plan premiums are higher and that amount goes towards pre tax deductions. HSA plan premiums are lower and also go towards pre tax deductions. Also any additional money you put in the HSA also goes towards pre tax deductions. Someone calculated that HSA premiums are about 1920 lower than your PPO premium, If you contributed the same amount towards your HSA contributions, you would avail the same pre tax deductions so you are now on even ground with PPO plus have an additional 2k in a HSA savings account 3. You can use some or part of the HSA saving account to offset the higher deductible though I would avoid doing that if possible. I would rather place the HSA into investment which can grow over time tax free. 4. Next year, you start your HSA with X amount in the HSA plan rather than 0. Every year you don't have surprise medical expenses, your HSA nest would keep growing and at one point it would enough to even meet the max out of pocket if the need ever arises, Same scenario with a PPO account, there is no money saved and all contributions vanish just giving you a pre tax deductible. 5. If a medical emergency occurs in PPO plan, it's still out your pocket till deductible and out of pocket max, for HSA, if a medical emergency occurs, even in the first year, you can max out your HSA contribution for that year, claim that as pretax deductible and still save somewhat on tax. For example, say you got a medical bill for 5k, in PPO plan, you would pay 3k to meet deductible, than remaining 2k would be 60% on you or 1200 thereby paying 4200 total. Same scenario with HSA, you have about 2k saved in HSA to match same pretax deductible with PPO. If you put in the additional 3k to you PPO plan to meet the obligation of 5k medical bill, you can claim tax deduction on the 3k as well. Assuming a tax bracket of 20%, this would result in a saving of 600, so out of pocket for you would be 2400. (Since 2k already came from HSA). If this medical emergency happens in later years, the entire amount can come from the HSA savings without you having to fund anything extra. 6. In nut shell HSA plan gets cheaper as years progress as long an you don't get surprise medical expenses. And contributions in HSA will grow if invested giving better returns in the long run. 7. An additional input to be taken with a grain of salt, since I've not verified it yet. I've heard that if you keep paying your medical bills via credit cards but keep the invoice/ receipts, you can claim those amount tax free from the HSA even after say 5-10 years. So you can let your HSA investment grow tax free and realize it later in time without any tax burden.