Maxing out HSA after maxing out Roth IRA
Unless the hypothetical fellow is immune to disease, and indestructible, with no risk of injury, the HSA is an ideal place for this money.  It offers a pretax deposit, and if used for medical expenses, a tax free withdrawal. This combination can't be beat for those who have the medical insurance that qualifies them for the HSA.
If your employer matches a percentage of your contributions, then you should try to max out your plan. Once you have completed maxing out your 401k, you may want to open up an IRA for several reasons: will your 401k be enough to sustain your lifestyle in retirement? Your IRA allows you to save even more for retirement. you can invest in all sorts of stuff through your IRA that might not be available in your plan. you can withdraw the principal from your IRA, usually after five years. This serves as another form of savings. IRAs have some asset protection in the event of bankruptcy. A normal savings or investment account usually does not offer such protection. From what these people are saying, it is impossible for you to put $5,500 in if it were a Roth though, because the money has to be taxed. You are correct that this is wrong.  You can still put $5,500 in a Roth - the tax payment comes when you file, not when you make the investment.  This is when the Roth is better than a Traditional IRA, when you can invest the max either way.  Yes you get the tax break for the Traditional investment, and if you invest the tax savings you'll be in the same spot, all else being equal. If you only have a certain amount (after taxes) to invest, say $3,000 in a 25% marginal tax bracket, then it works out the same either way.  You can either invest $3,000 in a Roth and let it grow tax free, or put $4,000 in a traditional IRA since you can deduct $1,000 (15%) from your taxes when you file. Then your tax-adjusted balance when you withdraw is the same, since you'll have a lot more (33% more in fact) in your traditional IRA but will have to pay tax on the withdrawals. Some companies allow you to make a post-tax contribution to the 401K. This is not a Roth contribution. This can be money beyond the 18,000 or 24,000 401k limit. The best news is that eventually that money can be rolled into 1 Roth-IRA. Not all companies allow this option. One company I worked for did this automatically when you hit the annual max. Of course that was made more complex if you had multiple employers that year. If you have retirement savings, the HSA should not be considered in isolation, but as part of your complete asset allocation.  The HSA is a unique account in that the funds go in pre-tax, grow tax free, and then for qualified expenses, are withdrawn tax free. With healthcare being the biggest risk to one's retirement portfolio (i.e. a large unknown in that retirement budget), funding an HSA to the max, and treating it as a long term investment makes a lot of sense.  As a comment suggests, keeping what you feel is a year's worth of expenses liquid might make sense. The (medical) plan coverage should have a maximum out of pocket each year. That's another number you can use as a guideline.  The question is great, and as more people have the high deductible plan with an HSA, it's worth some analysis. The problem for those answering is that we don't know the rest of your situation. Specifically, how these funds fit into your portfolio of assets. Your math is correct. As you point out, because of the commutative property of multiplication, Roth and traditional IRAs offer the same terminal wealth if your tax rate is the same when you pull it out as when you put it in.  Roth does lock in your tax rate as of today as you point out, which is why it frequently does not maximize wealth (most of us have a higher tax bracket when we are saving than when we are withdrawing from savings). There are a few other potential considerations/advantages of a Roth: Roth and traditional IRAs have the same maximum contribution amount.  This means the effective amount you can contribute to a Roth is higher ($5,500 after tax instead of before).  If this constraint is binding for you and you don't expect your tax rate to change, Roth is better. Roth IRAs allow you to withdraw your contributed money (not the gains) at any time without any tax or penalty whatsoever.  This can be an advantage to some who would like to use it for something like a down payment instead of keeping it all the way to retirement.  In this sense the Roth is more flexible. As your income becomes high, the deductibility of traditional IRA contributions goes to zero if you have a 401(k) at work (you can still contribute but can't deduct contributions).  At high incomes you also may be disallowed from contributing to a Roth, but because of the backdoor Roth loophole you can make Roth contributions at any income level and preserve the full Roth tax advantage. Which type of account is better for any given person is a complex problem with several unknowns (like future tax rates).  However, because tax rates are generally higher when earning money, for most people who can contribute to them, traditional IRAs maximize your tax savings and therefore wealth. Edit: Note that traditional IRA contributions also reduce your AGI, which is used to compute eligibility for other tax advantages, like the child care tax credit and earned income credit.  AGI is also often used for state income tax calculation. In retirement, traditional IRA distributions may or may not be state taxable, depending on your state and circumstances. The first question is essentially asking for specific investment advice which is off-topic per the FAQ, but I'll take a stab at #2 and #3 (2) If my 401k doesn't change before I leave my job (not planned in the   near future), I should roll it over into my Roth IRA after I leave due   to these high expense ratios, correct? My advice is that you should roll over a 401K into an IRA the first chance you get (usually when you leave the job). 401K plans are NOTORIOUS for high expense ratios and why leave your money in a plan where you have a limited choice of investments anyway versus a self-directed IRA where you can invest in anything you want? (3) Should I still max contribute with these horrible expense ratios? If they are providing a match, yes. Even with the expense ratios it is hard to beat the immediate return of an employer match.  If they aren't matching, the answer is still probably yes for a few reasons: You already are maxing out your ability to contribute to sheltered accounts, so assuming you still want to sock away that money for retirement, the tax benefits are still valuable and probably offset the expense ratios. Although you seem to be an exception, it is hard for most people to be disciplined enough to put money in a retirement account after they have it in their hands (versus auto-deduction from paychecks). I'll summarize here our discussion in the comments. First thing to remember is that you can only deposit up to $6K/year into the Roth IRA, you cannot seed it with some large amount (unless its a rollover). Second thing to remember is that you can only qualify 10K distribution for the home purchase. With that in mind, it seems that you'll have to have extremly high returns to make use of the maximum tax benefit (15-20% of the 10K). Non-qualified distributions will be taxed at ordinary income rates + 10% penalty, so if you can't qualify the distribution, instead of saving money on taxes, you'll end up paying twice as much as you would have without the IRA. Also, keep in mind that reporting of the distributions and justifying the qualifications might require assistance of a tax preparer, which will also reduce your savings. Bottom line, IMHO, you'll end up with a wash or very insignificant savings (compared to the magnitude of the home purchase costs) at best, which renders the whole thing kindof wastefull. "See this question regarding the relationship between a HDHP (High Deductible Health Plan) and an HSA (Health Savings Account). In brief, to qualify for an HSA you must have a HDHP: HDHPs are plans with a minimum deductible of $1,200 for self-only coverage and $2,400 for self-and-family coverage. The maximum amount out-of-pocket limit for HDHPs is $5,950 for self-only coverage and $11,900 for self-and-family coverage. As mentioned by Stainsor, your insurance can either come from your employer, or it can be an individually purchased plan. The HSA can be bundled as part of a package with the insurance, or it can be an account you set up separately. Contributions you make to the HSA are tax deductible. You'll report the amount you contributed when you file your taxes the following year. E.g. in April 2012 you'll report (and deduct) the amount of HSA contributions you made for tax year 2011. I'm not sure what kind of trouble you'll get into if you have an HSA without having a qualified HDHP. To answer the main part of your question: Different HSAs may have slightly different features, but I've typically seen them provide the following ways to withdraw funds: Via a debit card issued with the account. You can use the debit card to pay for things like drugs at the pharmacy, or at a doctors' office that requires payment at the time of service. Via online bill pay. You can use this to pay bills from hospitals, doctors' offices, or other healthcare service providers that send you bills. Via paper checks. For doctors' offices that require payment at time of service but don't accept plastic. (Or if you prefer not to use online bill pay.) Via withdrawal at a teller window or ATM. You can use this to ""reimburse yourself"" for healthcare expenses that you paid out of pocket. The issue of documenting legitimate expenses and/or qualifying for the account with an HDHP is between you and the IRS. The bank at which your HSA is kept doesn't really care whether you comply with the tax laws."