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.
Your 1&2 are the end of that chapter. You can't convert for that year again, and must wait 30 days to convert in the new tax year.  For example, each year for over a decade, I've helped my mother in law with this. In May, we convert a chunk of money/stock to Roth. In April, I'll recharacterize just enough so she tops off her 15% bracket but doesn't hit 25%. 30 days later, the new conversion happens. All the Roth money is money now taxed at 15%, which, in an emergency, a need for a lot of cash, will avoid the potential of 25% or higher, tax. You see, your 3 never really happens. HSA's are one of the few accounts where the money is both tax free going in and coming out. For long term savings, the only account that might beat that is a 401(k) with an employer match. Unlike an FSA, the money can stay in the account indefinitely. You can also use the money to pay medical insurance premiums once you separate from the employer. An HSA combines the best features of a FSA, Roth account, and IRA/401(k) account. As such I think there is rarely a reason not to max one out, and in fact I think it is worth it to go out of your way to get access to one. There are some drawbacks, of course. If you don't use the money for medical expenses, it may be taxed and perhaps penalized. Getting access to one can be tricky (you have to be covered by an HDHP, but not by a non-HDHP, nor by an FSA). The low contribution limits make it hard to build up a large balance. Many providers charge a monthly fee of $1 to $4 if you want to invest the balance (small, but it adds up, especially given the low balance per previous sentence). "Unfortunately, not directly.  For IRAs and HSAs, we have an annual maximum contribution limit. What you can do (which doesn't ""initially seed"" it) is to put the money aside in a savings account that you want to contribute to your HSA or IRA and then put it in the IRA or HSA when the timing is right for you.  The key here though is that the contribution cannot exceed the maximum limit for the year. Another ""way around"" this (which really isn't because it just means that you'll have a new higher limit) is to become self employed, see this from the IRS about SEPs: Contribute as much as 25% of your net earnings from self-employment   (not including contributions for yourself), up to $51,000 for 2013   ($52,000 for 2014). Still, none of these methods are pre-seeding an account, as the maximum contribution limit is never exceeded." "Do you think that you had previously been over-saving for retirement? If so, then the first time home buyers exemption might be a good opportunity for you to reverse that error. On the other hand, if you think you have been saving the right amount, or too little, for retirement, then why would you undo that savings?  ""Because I can, under existing tax law"" seems like an inadequate answer. Remember that if you are anticipate to be maxing out your tax advantaged accounts in the near future, then such a distribution is a permanent loss of opportunity.  You can't get the money back in. Are you thinking more clearly now, or were you thinking more clearly back when you decided to contribute to an IRA rather than build up a down-payment fund in the first place?" I know in the instance that if my MAGI exceeds a certain point, I can   not contribute the maximum to the Roth IRA; a traditional IRA and   subsequent backdoor is the way to go. My understanding is that if you ever want to do a backdoor Roth, you don't want deductible funds in a Traditional account, because you can't choose to convert only the taxable funds. From the bogleheads wiki: If you have any other (non-Roth) IRAs, the taxable portion of any   conversion you make is prorated over all your IRAs; you cannot convert   just the non-deductible amount. In order to benefit from the   backdoor, you must either convert your other IRAs as well (which may   not be a good idea, as you are usually in a high tax bracket if you   need to use the backdoor), or else transfer your deductible IRA   contributions to an employer plan such as a 401(k) (which may cost you   if the 401(k) has poor investment options). I would not suggest closing out your Roth IRA -- Couple of reasons for that - 1) Since you've been contributing to it for 15 years, your investments have probably grown, seen dividends, etc.  If you close it out, you will owe taxes and be slapped with a 10% penalty on the growth (money you didn't contribute).  That's quite a waste of hard earned money.   2) While your income may exceed the contribution limit of a Roth, you could do what's called a 'backdoor' Roth - which is really just converting your after tax contributions into an IRA into a Roth IRA. 3) Given the length of your contributions your Roth IRA is seasoned (5 years) This allows you to use up to 10k for your house if you chose.  (Usually not an option people use) Other than that, consider paying off the student loans with the highest interest first. Assuming you max-out your Roth IRA with $5000 in inflation-adjusted contributions every year from 25-65, your balance at age 65 will depend on the post-inflation return you get in the account.  Assuming you withdraw 4% per year after that, here is what your income will be: (All numbers are in inflation-adjusted 2011 dollars.)   If your post-inflation return is zero - if you buy treasury bonds, money-market accounts, or something like that - you'll have a simple $5000 * 40 = $200,000, which will give you an income of around $8000 per year. If you get a 3% post-inflation return - e.g. fairly safe Muni bonds, corporate bonds, and boring stocks - you'll approximately double your money to around $393,000, giving you an income of over $15,000 per year. If you get a 6% return - e.g. more aggressive stocks and more risk-taking - you'll approximately double your money again to over $825,000.  A 4% withdrawal rate will give you an income of around $33,000 per year. Stocks have historically returned around inflation + 8% - that will get you over $1.4 million - and an annual income of over $56,000 per year. So, yes, it is feasible to retire on nothing but a maxed-out Roth IRA. IRS Publication 969 gives all the details about HSA accounts and High Deductible plans: According to your question you are covered by a plan that can have an HSA.  There a few points of interest for you: Contributions to an HSA Any eligible individual can contribute to an HSA. For an employee's   HSA, the employee, the employee's employer, or both may contribute to   the employee's HSA in the same year. For an HSA established by a   self-employed (or unemployed) individual, the individual can   contribute. Family members or any other person may also make   contributions on behalf of an eligible individual. Contributions to an HSA must be made in cash. Contributions of stock   or property are not allowed. That means that yes you could make a contribution to the HSA. Or if in the future you were the provider of the insurance you could have a HSA. Limit on Contributions  For 2015, if you have self-only HDHP coverage, you can contribute up   to $3,350. If you have family HDHP coverage you can contribute up to   $6,650. It sounds like you have a family plan. Additional contribution.   If you are an eligible individual who is   age 55 or older at the end of your tax year, your contribution limit   is increased by $1,000. Rules for married people.   If either spouse has family HDHP coverage, both spouses are treated as having family HDHP coverage. If   each spouse has family coverage under a separate plan, the   contribution limit for 2014 is $6,550. You must reduce the limit on   contributions, before taking into account any additional   contributions, by the amount contributed to both spouses' Archer MSAs.   After that reduction, the contribution limit is split equally between   the spouses unless you agree on a different division. The rules for married people apply only if both spouses are eligible   individuals. If both spouses are 55 or older and not enrolled in Medicare, each   spouse's contribution limit is increased by the additional   contribution. If both spouses meet the age requirement, the total   contributions under family coverage cannot be more than $8,550. Each   spouse must make the additional contribution to his or her own HSA. Note: most of the document was written with 2014 numbers, but sometimes they mention 2015 numbers. If both are covered under a single plan it should be funded by the person that has the plan. They may get money from their employer. They may be able to have the employer cover the monthly fee that most HSA administrators charge. The non employee can make contributions to the account but care must be taken to make ure the annual limits aren't exceeded. HSA contributions from the employees paycheck may reduce the social security tax paid by the employee. If the non-employee is self employed you will have to see how the contribution impacts the social security situation for the couple. If the non-employee is 55 or older it can make sense to throw in that extra $1000. The employer may not allow it to come from the paycheck contributions because they wouldn't necessarily know the age of the spouse, they may put a maximum limit based on the age of the employee. Much of this is incorrect. Aetna owns Payflex for starters, and it's your EMPLOYER who decides which banks and brokers to offer, not Payflex. An HSA is a checking account with an investment account option after a minimum balance is met. A majority of U.S. employers only OFFER an HSA option but don't contribute a penny, so you're lucky you get anything.  The easy solution is just keep the money that is sent to your HSA checking account in your checking account, and once a year roll it over into a different bank's HSA. The vast majority of banks offer HSAs that have no ties to a particular broker (i.e. Citibank, PNC, Chase). I have all my HSA funds in HSA Bank which is online but services lots of employers. Not true that most payroll deductions or employer contributions go to a single HSA custodian (bank).  They might offer a single bank that either contracts with an investment provider or lets you invest anywhere. But most employers making contributions are large or mid-market employers offering multiple banks, and that trend is growing fast because of defined contribution, private exchanges and vendor product redesigns. Basically, nobody likes having a second bank account for their HSA when their home bank offers one. Is it worth saving HSA funds until retirement? Yes Are there pros and cons from a tax perspective?  Mostly pros. This has all of the benefits of an IRA, but if you use it for medical expenses then you get to use the money tax free on the other side. Retirement seems to be the time you are most likely to need money for medical expenses. So why wouldn't you want to start saving tax free to cover those expenses? The cons are similar to other tax advantaged retirement accounts. If you withdraw before retirement time for non-medical purposes, you will pay penalties, but if you withdraw at retirement time, you will pay the same taxes you would pay on an IRA. I should note that I put my money where my mouth is and I max out my contribution to my HSA every year. 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. "You can (and definitely should) withdraw any part of the contribution that will put you over the contribution limit.  You can (and should if you need to) withdraw to repay any medical payments you made from outside the account.  You can (but should avoid at all costs) withdraw (distribute) from the HSA for non-medical reasons. Here's the IRS publication which covers this:  https://www.irs.gov/publications/p969 Here's the bit about distributions that covers what you're trying to do: You can receive tax-free distributions from your HSA to pay or be reimbursed for qualified medical expenses you incur after you establish the HSA. If you receive distributions for other reasons, the amount you withdraw will be subject to income tax and may be subject to an additional 20% tax. You don’t have to make distributions from your HSA each year.  It is better to pay from your checking and reimburse than to over-fund the HSA.  Best route forward is to reduce your contributions for the rest of the year, especially if continuing them will cause excess contributions.  Another nasty gotcha: Excess contributions.     You will have excess contributions if the contributions to your HSA for the year are greater than the limits discussed earlier. Excess contributions aren’t deductible. Excess contributions made by your employer are included in your gross income. If the excess contribution isn’t included in box 1 of Form W-2, you must report the excess as ""Other income"" on your tax return. Generally, you must pay a 6% excise tax on excess contributions. See Form 5329, Additional Taxes on Qualified Plans (Including IRAs) and Other Tax-Favored Accounts, to figure the excise tax. The excise tax applies to each tax year the excess contribution remains in the account.  You may withdraw some or all of the excess contributions and avoid paying the excise tax on the amount withdrawn if you meet the following conditions.  •You withdraw the excess contributions by the due date, including extensions, of your tax return for the year the contributions were made. •You withdraw any income earned on the withdrawn contributions and include the earnings in ""Other income"" on your tax return for the year you withdraw the contributions and earnings. If you will not be over your maximum contribution, let the contribution ride.  Make sure your HSA balance is divided between cash, stock fund, bond fund.  Much like your 401k.  Because the part that you don't spend on medical expenses this year can be spent in future years' medical expenses, and if you have anything left when you retire you can spend it on whatever you want.  And the funds, including growth, are not taxed until you distribute them. Bottom line:  if the funds will not cause excess contribution, leave them in.  Otherwise, take them out as soon as possible." "You would want to prioritize Roth and retirement over HSA. As the HSA is only for health and dental expenses, which you will always have, overfunding it will put you in a bit of a pickle for all of the life involved. For example, even if you or a loved one develop a strange & expensive ailment, the HSA will only cover the medical costs, but not any travel to specialists, hotel stays, home alterations, special vehicles, or lifestyle alterations (food, clothing). However, you will eventually stop working even if you are healthy throughout your life.  I would suggest that you treat the HSA as a part of your overall emergency fund, giving it a cap the same as you would normal non-retirement savings. Since you stated you have three young children, small and large medical expenses (such as braces, trips to the emergency room) are something that are almost guaranteed, thus having fairly large amount in the HSA would be very beneficial throughout their time with you. Once the children have left however, if you still have an overwhelming balance in your HSA, you may not want to add anymore to the HSA. Setting a cap for the HSA based off a certain number of years of deductible payments for medication would be a good place to start.  Roth accounts, whether it be within your company's 401k plan or the IRAs for yourself and your spouse, are single-handedly the best location for your money for long-term savings. Roth money grows tax-free, is immune to Required Minimum Distribution provisions, and will avoid estate escrow when going to one's beneficiaries. Even if you tap into the funds prior to age 59 1/2, you would only pay taxes on any investment growth, in addition to the 10% early withdrawal penalty. If you have established Roth IRA accounts and have an AGI that disallows you to further contribute to them, there is still a provision to get Roth funds contributed via conversion through what is commonly called a ""back door"" Roth." "Yes. A most emphatic yes.  I suggest you look at your 2014 return and project what 2015 will look like. I'd convert enough to ""top off"" the 15% bracket. Note, if you overshoot it, and in April 2016, see that you are say $5K into the 25% rate, you can just recharacterize the amount you went over and nail the bracket to the dollar.  If you have the time and patience, you can convert into 2 different Roth accounts. One account for one asset class, say large cap stocks/funds, the other, cash/bonds. In April, keep the account that outperformed, and only recharacterize the lagger. Roth Roulette is my name for this strategy. It's risk free, and has the potential to boost the value of your conversions.  Edit - To be clear, you are permitted to recharacterize (undo) any or all of the converted amount. You actually have until tax time (4/15 or so) plus the 6 month extension. You can recharacterize for any reason - A personal anecdote - I manage my mother in law's money. She is well under the 25% bracket cutoff. Each year I convert, and each April, recharacterize just enough to be at the top of the 15% bracket. Over $100K has been shifted from Traditional IRA to Roth by now. Taxed at 15% so her daughters will 'not' pay 25% when they withdraw. $10K in tax saved from uncle sam, for my effort of filling out paper twice a year for 12 years now. Well worth my effort." "Would I only have to pay regular taxes plus the excess contribution   tax on any contributions? Yes, you'll pay regular taxes plus the excess contribution taxes on the contributions until you withdraw. So what would be your gain in doing this? The whole point in HSA is to use pre-tax money for medical expenses, and you're not only going to use post-tax money - you'll pay extra tax for doing that (6% for each year the contribution remains in the account). Are you trying to get the ""employer match"" in this way? Maybe just ask for a raise instead? Would this cause problems for my employer in any way? Not sure, but it might. Is it possible to simply receive funds in my HSA even though I am not   eligible, and then transfer them to his HSA to avoid any penalties? No, HSA is a personal account. You can pay for dependents, but you can't move money between the accounts. You can roll over to your own account. See the IRS publication 969 for more details."