Single employee - paying for health insurance premiums with pre-tax money
The answer likely depends a bit on which state you are in, but this should be true for most states.  I don't know anything about Pennsylvania specifically unfortunately. The Affordable Care Act created the SHOP marketplace, which allows small businesses to effectively form larger groups for group coverage purposes.  SHOP stands for Small Business Health Options Program, and requires only one common-law employee on payroll. This would effectively allow you to offer group coverage without having a group.  Talk to your tax accountant for more details, as this is still very new and not necessarily well understood. There are some other options, all of which I would highly suggest talking to a tax accountant about as well.  HRAs (health reimbursement accounts) allow the employer to set aside pre-tax funds for the employee to use for approved medical expenses; they're often managed by a benefits company (say, Wageworks, Conexis, etc.).  That would allow your employee to potentially pick a higher deductible health plan which offers poorer coverage on the individual marketplace (with after-tax dollars) and then supplement with your HRA. There are also the concept of Employer Payment Plans, where the employer reimburses the employee for their insurance premiums, but those are not compatible with the ACA for the most part - although there seems to be a lot of disagreement as to whether it's possible to have something effectively the same work, see for example this page versus this for example. Pre tax insurance is not possible unless the emplyer provides hsa and do a payroll deduction. Obamacare is all post tax and you can do deduction if your expenses exceeds 10%of your income
You have to consider that taxes that you pay on the premiums is money definitely paid, while benefits being tax free won't save you a thing if you never receive the benefits. Basically a company who provides health insurance for their employees provides it as part of the employee's salary package. This is an expense by the company in its pursuit of making income. In general, tax deductions are available on any expense incurred in deriving income (the exception is when social policy allows deductions for other types of expenses). If you pay for your own health insurance individually, then this expense is not an expense for you to derive your income, and as such is not tax deductible. The answer seems to depend on where you live.  Perhaps you already found this, but the summary from the IRS is: The insurance laws in some states do not allow a corporation to purchase group health insurance when the corporation only has one employee. Therefore, if the shareholder was the sole corporate employee, the shareholder had to purchase his health insurance in his own name. The IRS issued Notice 2008-1, which ruled that under certain situations the shareholder would be allowed an above-the-line deduction even if the health insurance policy was purchased in the name of the shareholder. Notice 2008-1 provided four examples, including three examples in which the shareholder purchased the health insurance and one in which the S corporation purchased the health insurance. Notice 2008-1 states that if the shareholder purchased the health insurance in his own name and paid for it with his own funds, the shareholder would not be allowed an above-the-line deduction. On the other hand, if the shareholder purchased the health insurance in his own name but the S corporation either directly paid for the health insurance or reimbursed the shareholder for the health insurance and also included the premium payment in the shareholder’s W-2, the shareholder would be allowed an above-the-line deduction. The bottom line is that in order for a shareholder to claim an above-the-line deduction, the health insurance premiums must ultimately be paid by the S corporation and must be reported as taxable compensation in the shareholder’s W-2. https://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/S-Corporation-Compensation-and-Medical-Insurance-Issues I understand this to mean that you can only get the deduction in your case (having purchased it in your own name) if your state does not allow your S-Corp to purchase a group health plan because you only have one employee. (I don't know specifically if Illinois fits that description or not.)  In addition, there are rules about reporting health insurance premiums for taxes for S-Corp share members that you should also check.  Personally, I think that it's complicated enough that advice from a CPA or other tax advisor specific to your situation would be worth the cost. You can never use a health FSA for individual health insurance premiums.  Moreover, FSA plan sponsors can limit what they are will to reimburse.  While you can't use a health FSA for premiums, you could previously use a 125 cafeteria plan to pay premiums, but it had to be a separate election from the health FSA. However, under N. 2013-54, even using a cafeteria plan to pay for indivdiual premiums is effectively prohibited. In addition to stoj's two good points I'll add a couple more reasons: 3)  In some situations there are secondary factors involved that can make it a good deal.  These normally amount to cases where you can buy the insurance with pre-tax dollars but would have to pay the bills with post-tax dollars. 4)  Insurance companies know much better what things should cost and often have negotiated rates.  A rich person would generally be well-served to have health insurance for this very reason. "Before filing your first business tax return, you will need to choose a taxation method, either corporation or partnership. If you choose a partnership, then it's moot - your business income flows through to your personal taxes via form K-1. Also, regardless of your taxation method, you should consult a legal expert, since having your business pay off your personal debt would almost always be counted as income to you, and may cause you to lose the personal liability protections provided by the LLC (aka ""piercing the corporate veil""). Having a single-member LLC with no employees, you have to be very careful how you manage the finances of the business. Any commingling of personal and business could jeopardize your protections." There are two problems with your understanding: The companies I have worked for match based on a percentage of your salary. That is a percentage of your gross pay. It was not based on the percentage of your net pay or after-tax pay. Net pay would be too hard to know. What I mean is the amount of insurance, HSA, Flex spending accounts, etc. determine how much is taxable and thus what is your after-tax pay . In fact if you split between the Roth and Pre-tax forms of the 401K your retirement contribution would influence the amount of the after tax contribution. All matching funds no matter the nature of the contribution (pre-tax, post-tax, Roth) are always considered pre-tax. You didn't pay taxes on the money when it was credited to your account. The tax incentives for employer sponsored health insurance were designed to incentivize employers to provide the insurance and for employees to purchase the insurance.  Since your situation does not meet the requirements to take advantage of this incentive, you can not.  In the near future you should be able to take part in the government sponsored exchanges.  This may spur changes in how this works. After reading OP Mark's question and the various answers carefully and also looking over some old pay stubs of mine, I am beginning to wonder if he is mis-reading his pay stub or slip of paper attached to the reimbursement check for the item(s) he purchases.  Pay stubs (whether paper documents attached to checks or things received in one's company mailbox or available for downloading from a company web site while the money is deposited electronically into the employee's checking account) vary from company to company, but a reasonably well-designed stub would likely have categories such as Taxable gross income for the pay period: This is the amount from which payroll taxes (Federal and State income tax, Social Security and Medicare tax) are deducted as well as other post-tax deductions such as money going to purchase of US Savings Bonds, contributions to United Way via payroll  deduction, contribution to Roth 401k etc. Employer-paid group life  insurance premiums are taxable income too for any portion of the policy  that exceeds $50K. In some cases, these appear as a lump sum on the last pay stub for the year. Nontaxable gross income for the pay period: This would be sum total of the amounts contributed to nonRoth 401k plans, employee's share of group health-care insurance premiums for employee  and/or employee's family, money deposited into FSA accounts, etc. Net pay: This is the amount of the attached check or money sent via ACH to the employee's bank account. Year-to-date amounts: These just tell the employee what has been earned/paid/withheld to date in the various categories. Now, OP Mark said My company does not tax the reimbursement but they do add it to my running gross earnings total for the year. So, the question is whether the amount of the reimbursement is included in the Year-to-date amount of Taxable Income. If YTD Taxable Income does not include the reimbursement amount,  then the the OP's question and the answers and comments are moot; unless the company has really-messed-up (Pat. Pending) payroll software that does weird things, the amount  on the W2 form will be whatever is shown as YTD Taxable Income  on the last pay stub of the year, and, as @DJClayworth noted cogently, it is what will appear on the W2 form that really matters. In summary, it is good that OP Mark is taking the time to investigate the matter of the reimbursements appearing in Total Gross Income, but if the amounts are not appearing in the YTD Taxable Income, his Payroll Office may just reassure him that they have good software and that what the YTD Taxable Income says on the last pay stub is what will be appearing on his W2 form.  I am fairly confident that this is what will be the resolution of the matter because if the amount of the reimbursement was included in Taxable Income during that pay period and no tax was withheld, then the employer has a problem with  Social Security and Medicare tax underwithholding, and nonpayment of this tax plus the employer's share to the US Treasury in timely fashion. The IRS takes an extremely dim view of such shenanigans and most employers are unlikely to take the risk. You're on the right track, and yes, that small difference is subject to income taxes. Do you use a payroll service? I do the same thing and use my payroll software to tweak the salary until the paycheck is just a few dollars every month (we run payroll once a month), with the rest going to the 401(k) and payroll taxes. So we're rounding up just a bit just so there's an actual paycheck with a positive number, and a bit does get withheld for fed/state income tax.  Also keep in mind you can make a company match. If your plan is a solo 401(k) with just you and your wife as the sole employees, consider the 25% match for both of you. The match is not subject to payroll taxes because it is a company expense. IRS web page: http://www.irs.gov/Retirement-Plans/One-Participant-401(k)-Plans The FSA can only pay for expenses incurred after it was open.  This also applies in case of a mid-year change in election (such as due to marriage, divorce, child birth, etc.) For example, according to this page: You can only be reimbursed for qualifying expenses, from the election that was in place at the time the expense was incurred. So, say you had $500 available from January to June, then on July 1 had a qualifying event, you then elected $2000.  You can be reimbursed for up to $500 in expenses incurred prior to July 1, and then an additional $1500 in expenses incurred after (up to $2000 if you didn't use your full $500). More specifically, from the IRS Publication: Generally, distributions from a health FSA must be paid    only to reimburse you for qualified medical expenses you    incurred during the period of coverage. -- The HSA question is more complicated. I would talk to a tax accountant, or at minimum your benefits coordinator.  Also read the publication I linked above, the first part is about HSAs.  The short answer to your specific question: stop contributing to the HSA, unless you were contributing well under the limit of the HSA.  If you know your limit, and you know you're under it, you can continue contributing until April 15 of next year: If you fail to be an eligible individual during    2013, you can still make contributions, up until April 15,    2014, for the months you were an eligible individual. The general rule is you can contribute up to (1/12)*(your limit)*(number of months you were eligible).  So, if you changed jobs Oct 1, and you're single, then you could contribute (3250)*(1/12)*(9), or just over $2400 in total for the year.  If you've contributed less than that to date, you may continue contributing up to that amount - but again, contact your benefits coordinator or preferably a tax accountant, as the rules can be complicated. You definitely cannot deduct any expenses from the account that you incur after you are no longer eligible, and the rules on distributions are pretty complicated - and if you get it wrong, you may owe a 10% penalty on top of the tax you would normally owe, so there is significant incentive not to get it wrong. Here is a quote from the IRS website on this topic: You may be able to deduct premiums paid for medical and dental   insurance and qualified long-term care insurance for yourself, your   spouse, and your dependents. The insurance can also cover your child   who was under age 27 at the end of 2011, even if the child was not   your dependent. A child includes your son, daughter, stepchild,   adopted child, or foster child. A foster child is any child placed   with you by an authorized placement agency or by judgment, decree, or   other order of any court of competent jurisdiction. One of the following statements must be true. You were self-employed and had a net profit for the year reported on   Schedule C (Form 1040), Profit or Loss From Business; Schedule C-EZ   (Form 1040), Net Profit From Business; or Schedule F (Form 1040),   Profit or Loss From Farming. You were a partner with net earnings from self-employment for the year   reported on Schedule K-1 (Form 1065), Partner's Share of Income,   Deductions, Credits, etc., box 14, code A. You used one of the optional methods to figure your net earnings from   self-employment on Schedule SE. You received wages in 2011 from an S corporation in which you were a   more-than-2% shareholder. Health insurance premiums paid or reimbursed   by the S corporation are shown as wages on Form W-2, Wage and Tax   Statement. The insurance plan must be established, or considered to be   established as discussed in the following bullets, under your   business. For self-employed individuals filing a Schedule C, C-EZ, or F, a   policy can be either in the name of the business or in the name of the   individual. For partners, a policy can be either in the name of the partnership or   in the name of the partner. You can either pay the premiums yourself   or your partnership can pay them and report the premium amounts on   Schedule K-1 (Form 1065) as guaranteed payments to be included in your   gross income. However, if the policy is in your name and you pay the   premiums yourself, the partnership must reimburse you and report the   premium amounts on Schedule K-1 (Form 1065) as guaranteed payments to   be included in your gross income. Otherwise, the insurance plan will   not be considered to be established under your business. For more-than-2% shareholders, a policy can be either in the name of   the S corporation or in the name of the shareholder. You can either   pay the premiums yourself or your S corporation can pay them and   report the premium amounts on Form W-2 as wages to be included in your   gross income. However, if the policy is in your name and you pay the   premiums yourself, the S corporation must reimburse you and report the   premium amounts on Form W-2 as wages to be included in your gross   income. Otherwise, the insurance plan will not be considered to be   established under your business. Medicare premiums you voluntarily pay to obtain insurance in your name   that is similar to qualifying private health insurance can be used to   figure the deduction. If you previously filed returns without using   Medicare premiums to figure the deduction, you can file timely amended   returns to refigure the deduction. For more information, see Form   1040X, Amended U.S. Individual Income Tax Return. Amounts paid for health insurance coverage from retirement plan   distributions that were nontaxable because you are a retired public   safety officer cannot be used to figure the deduction. Take the deduction on Form 1040, line 29. "Yes, it's normal. If you ""buy"" your own disability insurance with after tax money, any payout you get is non taxable. If your employer ""buys"" your disability insurance with their own money, any payout you get is taxable. Since the payout is not 100% of your pre-disability income, most folks strongly prefer that the payout be non taxable. To achieve this, I pay the premiums on behalf of my employees (including myself) and then add that premium to their salary as a taxable benefit. In effect I paid it to them, then took it from them and used it to buy the insurance. (It has no impact on my corporate taxes since I can either deduct premiums or salaries, same either way.) This ensures they won't pay tax if they should collect. And I have had people collect, and it was non-taxable to them." "Allowances are calculated as your total deductions divided by the tax year's personal exemptions. As mentioned above it is a multiplier. For 2015 the standard deduction for a married couple filing jointly is $12,600 and each of you gets 1 personal exemption ($4,000 in 2015). That's a total of $12,600 + 2*($4,000) or $20,600. Divide this by the personal exemption and you get roughly 5 allowances. Now say your employer offers health insurance and a 401(k) plan. Your total health insurance (or ""cafeteria"" contributions) are $2,000 for the year, and your total 401(k) plan contributions are $6,000 for the year. This would give an additional $2,000 + $6,000 = $8,000 divided by $4,000 = 2 allowances. Thus you would file with 7 allowances. Note that tax credits are not included in the allowance calculation. That is because they do not affect your taxable income but rather directly reduce your taxes due." The benefits and taxes thing, in my opinion is the biggie. Most people don't realize that the cost to the company for a full-time employee with benefits can be 2x or even 3x the amount they see in their paycheck.  Health plans are extremely expensive. Even if you are having money taken from your check for health insurance, it is often just a fraction of the total cost, and the employer is subsidizing the rest.  More expensive benefits that contractors don't typically get are 401K matches and paid vacation days. When contractors call in sick or don't work because it is a national holiday, they don't get paid for that day. Also, see that line on your paycheck deducting for Social security and Medicare? That is only half of the tax. The employer pays an equal amount that is not shown on that statement. Also, they pay taxes that go towards unemployment benefits , and may be required to pay higher taxes if they churn through a lot of full-time employees. You can usually let contractors go with relative impunity . For the unemployment tax reasons, not paying for people's days off or benefits, a lot less paperwork, and less risk to the business associated with committing to full-time employees all provide value to the company. Thus companies are willing to pay more because they are getting more.  Think of it like a cell phone-contract. If you commit to a three year contract it can be a pain/expensive to get out of the deal early, but you will probably get a better rate in exchange for the risk being shifted to your end of the deal.