Are COBRA premiums deductible when self-employed?
"The basic idea is that the average person can't deduct health care costs unless they're really onerous. But a business can, and as a self-employed person, you can deduct those costs from the businesses earnings... as long as the business is really generating enough profit to cover the health insurance costs. That's why most people get their health insurance from their employer, actually. The relevant IRS rules say: ""You may be able to deduct premiums paid for medical and dental insurance and qualified long-term care insurance for you, your spouse, and your dependents if you are... A self-employed individual with a net profit reported on Schedule C (Form 1040)."" For 2010, thanks to the Small Business Jobs Act of 2010, you can even deduct the premium from your income before deducting the self-employment tax (Source). I'm sure that when you get your tax returns and instructions for 2010 this will all be spelled out." "I am very late to this forum and post - but will just respond that I am a sole proprietor, who was just audited by the IRS for 2009, and this is one of the items that they disallowed.  My husband lost his job in 2008, I was unable to get health insurance on my own due to pre-existing ( not) conditions and so we had to stay on the Cobra system.  None of the cost was funded by the employer and so I took it as a SE HI deduction on Line 29.  It was disallowed and unfortunately, due to AGI limits, I get nothing by taking it on Sch. A.  The auditor made it very clear that if the plan was not in my name, or the company's name, I could not take the deduction above the line.  In his words, ""it's not fair, but it is the law!""" http://www.ehow.com/about_4625753_cobra-as-selfemployed-health-insurance.html This link makes it clear... it has to be itemized, and is subject to the > than 7.5% AGI rule. When you take the self employed health care deduction on on Line 29 of form 1040 for 2010 it also will lower your self employment tax.  See line 3 of Schedule SE.  You report your net earnings from self employment less line 29 from 1040. COBRA premiums are not deductible on 1040 line 29; to qualify, the IRS says the insurance plan must be in your name (COBRA is in your former employer's name).  H&R Block confirms this. 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.
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. COBRA provides you the option to continue your coverage as you had during your employment, after you leave your job. It is optional, you need to actively elect it. Once you elect, coverage starts from the day your employment coverage ends. So to answer your questions: Yes, it is legal. You elected this yourself, no-one forced you. You cannot get your money back. You did have coverage in June-July-August, since your COBRA election provided coverage from the date you left your job. As to cancellation, from the DOL FAQ: Q12: Can continuation coverage be terminated early for any reason? A group health plan may terminate coverage earlier than the end of the   maximum period for any of the following reasons: If continuation coverage is terminated early, the plan must provide   the qualified beneficiary with an early termination notice. The notice   must be given as soon as practicable after the decision is made, and   it must describe the date coverage will terminate, the reason for   termination, and any rights the qualified beneficiary may have under   the plan or applicable law to elect alternative group or individual   coverage. If you decide to terminate your COBRA coverage early, you generally   won't be able to get a Marketplace plan outside of the open enrollment   period. For more information on alternatives to COBRA coverage, see   question 4 above. The idea is that the premiums (or costs) associated with the plan are a business expense, you know that already.  The distinction here is that employees don't pay premiums, they elect to contribute. The company sponsors a plan, the employees then choose to accept less salary in order to participate in the employer's plan.  The idea is that you're foregoing income. Why is the employee not taxed on this cost?  One major reason is that the employee has no say in, and often no idea, what the gross costs are (some find out if they ever receive COBRA election paperwork). There are more benefits than strict healthcare that are Section 125 eligible.  The government has a vested interest in keeping the population healthy, and when the ERISA laws and Section 125 were written it was (and still is) a pretty low friction way to get health insurance out to more people.  At this point, taking away the tax break from the employees would be a huge government take away from most of the population.  Try to get a politician to take something away from taxpayers. Why doesn't the deduction exist in kind to people buying individual coverage?  Ask your legislators.  There are thousands of preferential tax treatment oddities, where some industry will get some sort of benefit or break.  I'm not sure what leads you to think there needs to be some supremely logical reason for this oddity to exit. IRS Publication 529 is the go-to document.  Without being a tax professional, I'd say if the dues and subscriptions help you in the running of your business, then they're deductible. You're on your own if you take my advice (or don't). ;) "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." No not deductible. But - If you work more than one job, you run the risk of having too much SS withheld. Each employer doesn't know what the others pays you. Tax time reconciles this.  And much thanks to Dilip for the following clarification - Not only does each employer not know what the others pays you, but even if you tell him, he will not care. He is required to withhold Social Security tax on the wages he pays you (and send in an equal amount as his contribution) regardless of what anyone else pays you. If the sum of your taxable wages from all employers exceed the maximum wages subject to Social Security, the excess withholding is credited towards the income tax due (and thus reduces the amount to be paid or increases the refund you are owed) but the employer's (excess) contribution that he sent in is not returned to him..... Also, there is no such things as excess Medicare tax having been withheld because there is no maximum wage beyond which Medicare tax does not apply. "This is an unfortunate situation for you.  You have zero chance at your question number 1, if someone was going to bend this rule for you it would have happened already.  The answer to question number 2 is pursue solution number 3. The overriding issue is that the IRS makes these rules, not the employer/plan sponsor or the administrator.  You can't talk the plan administrator in to reimbursing you, their system likely doesn't even have a function to do so. FSA timing issues can be complex and I think that's the root of your issue because when an expense can be incurred (date of service versus date of payment) and when a claim must be filed are different things. It's really common to bend the rules on when a claim is submitted, but not when it was incurred.   It's really common for an exiting employee to have 30 days to submit expenses for reimbursement.  FSA expenses must always be incurred within the specified plan year, or within your dates of employment if you weren't employed for the entire plan year, this is specified by the IRS.  It seems like some wires were crossed when you asked this question.  You were asking ""can I still incur claims"" and they were hearing ""how long do I have to submit an expense that has already been incurred."" Some plans allow COBRA continuation on FSA which generally does not make sense.  Your contributions to the plan would use after tax dollars but for folks who know they have an eligible expense coming it can make sense to continue via COBRA in retain your eligibility under the plan so you can incur a claim after your employment termination. Regarding number 3.  This sort of reimbursement would be outside the plan, no precedent is necessary.  You've gotten them to claim it was their mistake, they're going to reimburse you for their mistake, it has nothing to do with the FSA. Good luck." It depends on the finances involved, but particularly if you're not billing anything right now and may have no revenue this year, it's probably a good idea to bill his company. This is in part because some deductions or other tax treatments are only allowed if you have revenue and/or income.  The biggest example I can think of is the Solo 401k - you can only contribute up to your self employed income.  If you're planning to contribute to one (and you should, they're amazingly powerful tools for saving for retirement and for reducing your tax burden), you will have to have some revenue in order to have something to pay yourself with. I don't believe you have to charge him, though, if it makes more tax sense not to (for example, if his business is operating at a loss and cannot benefit from expensing it, but you'd then have to pay taxes on your own income from it). "This is really unfortunate.  In general you can't back date individual policies.  You could have (if it was available to you) elected to extend your employer's coverage via COBRA for the month of May, and possibly June depending on when your application was submitted, then let the individual coverage take over when it became effective.   Groups have some latitude to retroactively cover and terminate employees but that's not an option in the world of individual coverage, the carriers are very strict about submission deadlines for specific effective dates.  This is one of the very few ways that carriers are able to say ""no"" within the bounds of the ACA.  You submit an application, you are assigned an effective date based on the date your application was received and subsequently approved.  It has nothing to do with how much money you send them or whether or not you told them to back date your application. If someone at the New York exchange told you you could have a retroactive effective date they shouldn't have. Many providers have financial hardship programs.  You should talk to the ER hospital and see what might be available to you.  The insurer is likely out of the equation though if the dates of service occurred before your policy was effective. Regarding your 6th paragraph regarding having paid the premium.  In this day and age carriers can only say ""no"" via administrative means.  They set extremely rigid effective dates based on your application date.  They will absolutely cancel you if you miss a payment.  If you get money to them but it was after the grace period date (even by one minute) they will not reinstate you.  If you're cancelled you must submit a new application which will create a new coverage gap.  You pay a few hundred dollars each month to insure infinity risk, you absolutely have to cover your administrative bases because it's the only way a carrier can say ""no"" anymore so they cling to it." The short answer is yes you probably can take the deduction for a home office because the space is used exclusively and you are working there for the convenience of your employer if you don't have a desk at your employers office. The long answer is that it may not be worth it to take the home office deduction as an employee. You're deduction is subject to a 2% AGI floor. You can only deduct a percentage of your rent or the depreciation on your home. A quick and dirty example if you make $75k/year, rent a 1200 sqft 2 bedroom apartment for $1000/month and use one bedroom (120 sqft) regularly and exclusively for your employer. You can deduct 10% (120sqft/1200sqft) of the $12000 ($1000*12 months (assumes your situation didn't change)) in rent or $1200. However because you are an employee you are subject to the 2% AGI floor so you can deduct $1200-$1500 (75000*.02 (salary * 2% floor)) = -300 so in order to deduct the first dollar you need an additional $300 worth of deductible expenses.  Depending on your situation it may or may not be worth it to take the home office deduction even if you qualify for it. "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." That depends on your health insurance. PIP will often cover your missed work as a result of an injury - which isn't a problem if you health insurance also does this but there is a chance it does not. What would you and your wife do for money if you became paralyzed? What you need to do is register as a sole trader. This will automatically register you for self assessment so you don't have to do that separately. For a simple business like you describe that's it.  Completing your self assessment will take care of all your income tax and national insurance obligations (although as mentioned in your previous question there shouldn't be any NI to pay if you're only making £600 or so a year). "Can she claim deductions for her driving to and from work? Considering most people use their cars mostly to commute to/from work, there must be limits to what you can consider ""claimable"" and what you can't, otherwise everyone would claim back 80% of their mileage. No, she can't. But if she's driving from one work site to another, that's deductible whether or not either of the work sites is her home office. Can she claim deductions for her home office? There's a specific set of IRS tests you have to meet. If she meets them, she can. If you're self-employed, reasonably need an office, and have a place in your house dedicated to that purpose, you will likely meet all the tests. Can I claim deductions for my home office, even though I have an official work place that is not in my home? It's very hard to do so. The use of your home office has to benefit your employer, not just you. Can we claim deductions for our home internet service? If the business or home office uses them, they should be a deductible home office expense in some percentage. Usually for generic utilities that benefit the whole house, you deduct at the same percentage as the home office is of the entire house. But you can use other fractions if more appropriate. For example, if you have lots of computers in the home office, you can deduct more of the electricity if you can justify the ratio you use. Run through the rules at the IRS web page." "Income from a hobby is tax exempt under Dutch law. To consider whether it's hobby, a few rules are applied such as: How much time do you spend on the activity? And is the hourly wage low? Obviously, having a boss is a sure sign of it not being a hobby. The typical example is making dolls and selling them on a crafts fair. If you travel the country and sell each weekend on a different fair, that's a lot of time. If you only sell them on the fair in your home town, it's a hobby.  Situation 3 is the most difficult. If you just happened to luck out, it's still a hobby. If you spent significant time to improve the value of your holdings, e.g. by trading in-game, then it might be seen as work. In the latter case, you simply file it as ""income from other sources, not yet taxed"".  For the purpose of determining income from a hobby, you may deduct actual expenses. So, in your case they'd look at the net income of $-1000, which is not unusual for a hobby. It wouldn't be any different if you took up horse riding, decided that you didn't like it, and sell your horse at a loss."