Can I deduct my individual Health Insurance Premium in Tax
"Yes, you can. See the instructions for line 29 of form 1040. Self employed health insurance premiums are an ""above the line"" deduction."
"To claim medical expenses on your taxes they need to exceed 7.5% of your AGI, and then only the amount over 7.5% is deductible.  That's not much.  There is no ""floor"" if you use an FSA as it's all pre-tax. If you're concerned about use or lose, then allot less next year.  It's all what you're comfortable with." During World War II, the United States (US) instituted wage and price controls.  To attract better employees, companies would offer benefits to get around salary limits.  Health insurance was one of the more successful benefits.   At that time, income taxes were newer and there were many ways to evade them.  Companies could generally deduct expenses.  So at that time, health care was deductible because everything was.  And at that time, only wages were taxable compensation from employer to employee.   Since that time, many other benefits have become non-deductible for employers, e.g. housing or the reduced deduction for meals and entertainment.  But health care is generally regarded as different, as a necessity.  While everyone needs to eat, not everyone needs to eat at a $100 a meal restaurant.  People who need expensive health care really need it.  People who eat expensive food just prefer it.   And of course, health care is more intermittent where food is relatively consistent.  You don't need ten thousand calories one day and zero the next.  But some families have no health care expenses in a year while another might have cancer or a pregnancy.  Note that medical care expenses can be deducted for individuals if they are large enough in aggregate and you itemize.   And of course both businesses and workers have incentives to maintain the current system with deductibility.  Health insurance is a common benefit.  Housing is not (although it's worth noting that travel housing and meals are deductible).  So there have been few people impacted by making housing taxable while many people would be impacted by taxable health insurance.   You can deduct health insurance costs if self-employed.  It's also not true that health insurance is the only benefit with preferential tax treatment.  Retirement and child care are also deductible.  Even meals and housing can be deducted in certain circumstances.  The complex rules about what and how much is deductible.   There have been rumbles about normalizing the tax treatment of health insurance and medical care, but there is a lot of opposition.  Insurance companies oppose making all healthcare expenses deductible, as that reduces their effective benefit.  They would prefer only insurance premiums be deductible.  Traditionally employed individuals oppose making health insurance taxable, as that would increase their taxes.  So the situation persists.  There isn't quite enough support to move in either direction, although the current compromise is economically silly. Currently certain money back policies are tax free and a vast majority are taxable. There are revised guidelines that would govern which policies are tax free. At a broad level the rule is that the sum assured under the policy should be 10 times the premium paid. There is no distinction of single premium or yearly. Hence certain policies of single premium are taxable. Further there is a TDS also in place from this year. This article gives a good overview. You should consult the documentation of your specific policy and check with your insurance company or CA. As far as taxes go: If you contribute to the HSA account through your employer pre-tax, that amount is not subject to the Social Security (6.2%) and the Medicare (1.45%) tax. If you contribute that amount post-tax, you can deduct it from your income tax at the end of the year, but the Social Security and Medicare taxes have already been paid and there's no mechanism to claim deductions on those. There are several insurance products that I buy for legal reasons: Both of these protect me from lawsuits and fines. Many people buy similar products to protect their business operations. (e.g. medical malpractice insurance) There are some insurance products I buy for tax planning and financial planning purposes: I have a large amount of savings available, so I have several tricks to reduce my insurance costs, and I have several products that I avoid. Several of these reasons are mentioned in other answers, but I thought I would collect them into a single answer to demonstrate that there are reasons other than the rational calculation of what the payout will be for the insurance products vs. the premium paid. If I gain access to a tax advantaged Health savings account, that is a bigger benefit to me than avoiding the premium, especially when my employer is paying the majority of the premium. Perhaps it makes no sense to buy insurance given sufficient savings (like the products I listed that make no sense for me given my finances) but not everyone can self-insure; it does require a certain level of wealth. 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. As others have pointed out, post-tax dollars are what you'll use.  Just as a quick note, as you'll be using post-tax dollars; in the past, I've refused to take contractor plans because they almost always are inferior to what I've been able to get off the private exchange ehealthinsurance.  A few people have written excellent articles on Get Rich Slowly here and here about them in detail if you want more information. Generally, contractors (and sometimes employees) are offered a few plans (3-4), and this health exchange gives you a little more freedom to pick your plan, which in your situation may help.  It isn't always cheaper, but depending on your needs, you may obtain a better deal. Forgot to add this: this option has also made switching jobs easy as well since I don't have to pay COBRA.  While it depends on the situation, this can sometimes come out significantly cheaper.  For instance, if I were to take the employer health plan next year, I would lose ~$450 a month, whereas the private exchange option is ~$300.  But, if I were to switch jobs, decide to opt for self-employment, or a layoff, the COBRA would be even higher than ~$450. 1)  When you apply for insurance you indicate your expected income, they figure the subsidy based on this.  Note that while this data isn't checked it's only an estimate, any errors will be fixed at tax time so lying is just going to gain you an unpleasant tax bill come April 15. 2)  It's not paid in installments, it's just a monthly premium.  It's quite possible for someone to be on the ACA for only part of a year. 3)  I can't address the issue of the fines.  However, you are wrong on who it's for--it's for anyone who doesn't have employer-provided insurance, whatever the reason.  I've been on it since it's inception because I have been self employed for most of that time--there's no employer to even offer me insurance. "No, not on schedule C, better. Its an ""above the line"" deduction (line 29 on your 1040). Here's the turbo tax article on it. The instructions for this line set certain limitations that you must take into the account, and yes - it is limited to the net profit from the business. One of the following statements must be true. You were self-employed and had a net profit for the year. You were a partner with net earnings from self-employment. 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. The insurance plan must be established under your business. Your   personal services must have been a material income-producing factor in   the business. If you are filing Schedule C, C-EZ, or F, the policy can   be either in your name or in the name of the business." As a general rule, you must choose between a mileage deduction or an actual expenses deduction.  The idea is that the mileage deduction is supposed to cover all costs of using the car.  Exceptions include parking fees and tolls, which can be deducted separately under either method.  You explicitly cannot deduct insurance costs if you claim a mileage deduction.   Separately, you probably won't be able to deduct the deductible for your car as a casualty loss.  You first subtract $100 from the deductible and then divide it by your Adjusted Gross Income (AGI) from your tax return.  If your deductible is over 10% of your AGI, you can deduct it.   Note that even with a $1500 deductible, you won't be able to deduct anything if you made more than $14,000 for the year.  For most people, the insurance deductible just isn't large enough relative to income to be tax deductible.   Source "While COBRA premiums are not eligible to be a ""business"" expense they can be a medical expense for personal deduction purposes.  If you're itemizing your deductions you may be able to deduct that way.  However, you will only be able to deduct the portion of the premium that exceeds 10% of your AGI. Are you a full time employee now or are you a 1099 contractor?  Do you have access to your employers health plan?" While the OP disses the health insurance coverage offered through his wife's employer as a complete rip-off, one advantage of such coverage is that, if set up right (by the employer), the premiums can be paid for through pre-tax dollars instead of post-tax dollars. On the other hand,  Health insurance premiums cannot be deducted on Schedule C by self-employed persons. So the self-employed person has to pay both the employer's share as well as the employee's share of Social Security and Medicare taxes on that money. Health insurance premiums can be deducted on Line 29 of Form 1040 but only for those months during which the Schedule C filer is neither  covered nor eligible to be covered by a subsidized health insurance plan maintained by an employer of the self-employed person (whose self-employment might be a sideline) or the self-employed person's spouse. In other words, just having the plan coverage available through the wife's employment, even though one disdains taking it, is sufficient to make a Line 29 deduction impermissible.  So, AGI is increased. Health insurance premiums can be deducted on Schedule A but only to the extent that they (together with other medical costs) exceed 10% of AGI. For many people in good health, this means no deduction there either. Thus, when comparing the premiums of health insurance policies, one should pay some attention to the tax issues too. Health insurance  through a spouse's employment might not be that bad a deal after all. 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 can deduct what you pay for your own and your family's health insurance regardless of whether it is subsidized by your employer or not, as well  as all other medical and dental expenses for your family, as an itemized deduction on Schedule A of Form 1040, but only to the extent that the  total exceeds 7.5% of your Adjusted Gross Income (AGI) (10% on tax returns for year 2013 onwards). As pointed out in KeithB's comment, you cannot deduct any health insurance premium (or other medical expense) that was paid for out of pre-tax dollars, nor indeed can you deduct any medical expense to the extent that  it was paid for by the insurance company directly to hospital or doctor (or reimbursed to you) for a covered expense; e.g. if the insurance company reimbursed you $72 for a claim for a doctor's visit for which you paid $100 to the doctor, only $28 goes on Schedule A to be added to the amount that you will be comparing to the 7.5% of AGI threshold, and the $72 is not income to you that needs to be reported on Form 1040. Depending on other items on Schedule A, your total itemized deductions might not exceed the standard deduction, in which case you will likely choose to use the standard deduction. In this case, you ""lose"" the deduction for medical expenses as well as all other expenses deductible on Schedule A. Summary of some of the discussions in the comments   Health care insurance premiums cannot be paid for   from HSA accounts (IRS Pub 969, page 8, column 2, near   the bottom) though there are some exceptions.  Nor   can health care insurance premiums be paid from an   FSA account (IRS Pub 969, page 17, column 1, near the top). If you have a business on the side and file a Schedule C as a self-employed person, you can buy medical insurance for that business's employees (and their families too, if you like) as an employment benefit, and pay for it out of the income of the Schedule C business, (thus saving on taxes). But be aware that if you have employees other than yourself in the side business, they would need to be covered by the same policy too.  You can even decide to pay all medical expenses of your employees and their families too (no 7.5% limitation there!) as an employment benefit but again, you cannot discriminate against other employees (if any) of the Schedule C business in this matter.  Of course, all this money that reduced your Schedule C income does not go on Schedule A at all. If your employer permits your family to be covered under its health insurance plan (for a cost, of course), check whether you are allowed to pay for the insurance with pre-tax dollars.  The private (non-Schedule C) insurance would, of course, be paid for with post-tax dollars.  I would doubt that  you would be able to save enough money on taxes to make up the difference between $1330/month and $600/month, but it might also be that the private insurance policy covers a lot less than your employer's policy does.  As a rule of thumb, group insurance through an employer can be expected to offer better coverage than privately purchased insurance. Whether the added coverage is worth the additional cost is a  different matter.  But while considering this matter, keep in mind that privately purchased insurance is not  always guaranteed to be renewable, and a company might decline to renew a policy if there were a large number of claims. A replacement policy might not cover pre-existing conditions for some time (six months? a year?) or maybe even permanently.  So, do consider these aspects as well.  Of course, an employer can also change health insurance plans or drop them entirely as an employment benefit (or you might quit and go work for a different company), but as long as the employer's health plan is in existence, you (and continuing members of your family) cannot be discriminated against and denied coverage under the employer's plan." My understanding is that it works as you describe.  Is this really a loophole? You could call it that if you want, but let's look at what really is happening. You get the tax deduction when you put money into the HSA, not when you take money out. And you can only put money in when you have the HSA-eligible High Deductible Health Plan (HDHP) in place.  While you had the non-HSA eligible plan in place (presumably a more expensive low deductible health plan), you somehow incurred $5000 of out-of-pocket expenses. This is real money that you had to pay out.  Finally, you went back to the HDHP and began contributing to the HSA again, taking the tax deduction as you put money in, subject to the contribution limits. The money that is in the HSA is yours, and you had legitimate out-of-pocket medical expenses. Are you really cheating anybody out of anything if you choose to take that money back out? I don't think so.