When you enter the realm of health care sharing ministries, you join a community where like-minded individuals unite to share medical costs. It’s not your typical health insurance. You will discover why, for many, the lower monthly expenses make health care sharing ministries an attractive option, even without traditional tax benefits.

If you are on Medicare and you gamble, there’s a good chance that your gambling increases your cost of Medicare, even when you lose money.

Are you eligible for COVID-19 tax credits for yourself and/or your employees? Have you reimbursed your employees (including your employee spouse) as stipulated in your health reimbursement arrangements? And if you operate as an S corporation, do you have your health insurance set up correctly for your best tax deduction? In this article, we help with these matters and more.

If you discriminate when you contribute to the health savings accounts (HSAs) of your employees, the IRS will make you pay a 35 percent penalty tax on the total amount of your contributions. This tax can add up quickly, and if you have to pay it, you’ll kick yourself when you discover you can escape the tax entirely by following the three rules in this article.

As a business owner with fewer than 50 employees, you should consider the health savings account (HSA) as an option if you don’t want to provide health coverage to your employees. And of course, if you don’t have any employees, you should consider the HSA.

Although the Individual Coverage HRA (ICHRA) works for businesses of all sizes, it’s particularly helpful for small businesses with fewer than 50 employees that want to provide health care benefits to their employees. With an ICHRA, a business can reimburse individually purchased health insurance without triggering the $100-a-day-per-employee penalty.

The individual coverage HRA (ICHRA) has much to offer a small business (businesses with fewer than 50 employees). We addressed many of those in ICHRA: Game Changer for Small Business Health Benefits. Here we expand on the abilities of the ICHRA to get a smile from you, the small-business owner who wants to offer health benefits to his or her employees.

During 2021, the COVID-19 pandemic forced many self-employed individuals and corporate owner-employees to miss work. To offset this trouble, the federal government provided up to four possible sick and family leave tax credits. If you failed to claim the credits, you still have time to do so.

The COVID-19 pandemic forced many self-employed individuals and small corporate owner-employees to miss work for personal reasons, such as staying home to care for children whose schools or childcare providers were unavailable due to the pandemic. To offset this trouble, the federal government provided sick and family leave tax credits. If you failed to claim the credits until now, you still have time to do so.

If you can qualify to put a Section 105-HRA plan in place for your business, you qualify for some great tax benefits and perhaps even create tax deductions where none existed before. Three types of small businesses can put this plan in place: (1) the Schedule C taxpayer with no employees other than his or her spouse; (2) the Schedule C taxpayer with a buddy Schedule C taxpayer, both of whom create Section 105-HRA plans; and (3) the solo employee-owner of a C corporation.

Is it possible for an S corporation to pick up, say, the $21,000 tab for the more-than-2-percent shareholder’s family health insurance—and put that in box 1 of the shareholder’s W-2 as wages—but for the shareholder to get a zero deduction on Form 1040, Schedule 1, line 17? Yes, this can happen when an ugly rule comes into play.

Small and solo business owners face some tricky yet often rewarding rules when it comes to business tax deductions for health insurance and other medical expenses. In this article, you’ll find answers to six questions that will help you along the path to your rightful business deductions.

Health savings accounts (HSAs) are the best retirement account ever invented. You can help fund your HSA by making a once-in-a-lifetime rollover of money from your IRA. No tax need be paid on the rollover. Thus, if you later withdraw the funds from your HSA for medical expenses, you’ll never pay taxes on them. The only drawback is that the rollover amount is limited to your HSA contribution limit for the year. But hey, tax-free is free.

IRS Notice 2015-17 permits S corporations to escape the $100-a-day penalties on reimbursements they make to more-than-2-percent shareholder-employees for individually purchased health insurance.

When looking for tax law guidance from proposed regulations, be alert. If the regulations are not effective until finalized as is the case for health care sharing ministries, you could go down the wrong path and find yourself in trouble.

You may want to amend your existing health reimbursement accounts, medical savings plans, and flexible spending accounts to allow non-prescription over-the-counter drugs and menstrual care products.

If you’re thinking of becoming self-employed or recently took the plunge, this article is for you. One of the first things you need to consider is the self-employment tax, which starts almost immediately. And the second thing you need to consider is how to reduce your taxes. You will find good ideas in this article.

A Health Savings Account (HSA) can be the best retirement account of all because it offers triple tax benefits: (1) deductible contributions, (2) tax-free growth, and (3) tax-free withdrawals for medical expenses. No other tax-advantaged account gives you all three.

Taxable income has consequences. It causes income taxes. And it causes you to pay either more or less for Medicare. It boils down to this: there’s always a need to reduce your taxable income.

Are you eligible for COVID-19 tax credits for yourself and/or your employees? Have you reimbursed your employees (including your employee spouse) as stipulated in your health reimbursement arrangements? And if you operate as an S corporation, do you have your health insurance set up correctly for your best tax deduction? In this article, we help with these matters and more.

The self-employed normally get the short end of the stick when it comes to government aid in times of economic disruption. But the COVID-19 pandemic is different. Congress has provided the self-employed with aid never seen before, including forgivable PPP loans, tax credits for sick leave and family leave, increased Affordable Care Act subsidies, and even unemployment benefits. But the benefits are temporary, so take advantage of them now.

With the passage of the American Rescue Plan Act of 2021, Congress has temporarily abolished the health insurance premium tax credit “subsidy cliff.” For 2021 and 2022, self-employed and small-business owners and other individuals who must purchase individual health insurance may qualify for premium tax credit health insurance subsidies even if their income far exceeds the old limit of 400 percent of the federal poverty level.

The CARES Act made many temporary changes in the tax law. The new Consolidated Appropriations Act adjusted some of these and left others to die on December 31, 2020. With all the changes that took place in 2020, you need to know what’s left, enhanced, and over with, as we explain in this article.

Do you operate your business as an S corporation? It’s a popular choice due to the tax savings you benefit from. But if you don’t avoid the pitfalls, you risk losing those valuable tax benefits. Download this guide to maximize your S corporation tax savings and avoid common missteps.

Lawmakers passed significant COVID-19 relief legislation in December 2020. As part of this relief package, there are many tax changes that impact tax years 2020 and 2021. The changes put cash in your pocket. You will want to learn about them so you can use them to your advantage.

ABLE accounts allow disabled individuals and their family members to save a substantial amount of money without losing government benefits. The money grows tax-free and can be withdrawn tax-free to use for a wide variety of expenses. But only people who became disabled or blind before age 26 qualify for these tax-advantaged accounts.

If you become an executor of your loved one’s estate, you may have some important tax decisions to make, as we describe in this article. For example, on the decedent’s final Form 1040, should you elect to deduct medical expenses that are unpaid at the date of death? Should you file Form 706 when not required by law to do so?

The massive new stimulus law contains eight new tax breaks that help the average non-business taxpayer. These include something for everyone, both rich and poor. Wealthy taxpayers can contribute more to charity and still get a deduction; average people get an extension of the universal charitable deduction; and low-income taxpayers can get a larger earned income tax credit. Popular programs such as the lifetime learning credit are expanded to help more people. The bill also extends some favorable tax rules, such as the 7.5 percent adjusted gross income floor for the medical deduction.

Are you eligible for COVID-19 tax credits for yourself and/or your employees? Have you reimbursed your employees (including your employee spouse) as stipulated in your health reimbursement arrangements? And if you operate as an S corporation, do you have your health insurance set up correctly for your best tax deduction? In this article, we help with these matters and more.

Business owners who have established 105-HRAs, Qualified Small Employer Health Reimbursement Arrangements (QSEHRAs), and Individual Coverage Health Reimbursement Accounts (ICHRAs) to reimburse their employees for medical expenses need to pay an annual fee to help support the Patient-Centered Outcomes Research Institute (PCORI).

The new individual coverage HRA (ICHRA) has much to offer a small business (businesses with fewer than 50 employees). Last month we introduced the ICHRA. In this article, we expand on the abilities of the ICHRA to get a smile from the small-business owner who wants to offer health benefits to his or her employees.

When you get busy with your business, it’s easy to forget about your retirement accounts and medical coverages and plans. But year-end is approaching, and now’s the time to take action. This article gives you six action steps for 2019 that can help you reduce your taxes and pocket extra money.

The ACA destroyed a lot of the advantages of the Section 105 medical reimbursement plan. While the QSEHRA was, and remains, a good option for small employers, something even better has arrived—for employers of all sizes—starting in 2020.

Assisted living and nursing home expenses can quickly deplete your income and savings. One way to minimize their financial hit is being able to deduct them as medical expenses on your tax return. We’ll explain when you can do this.

There’s no excuse for it, but how to treat the payroll taxes (Social Security, Medicare, and federal unemployment taxes (FUTA) when the S corporation pays for or reimburses health insurance for the more-than-2-percent shareholder-employee sits in muddy waters—but perhaps only until you read this article.

Inside this 22-page medical deduction guide, you will find business and personal tax deductions that you would likely overlook. For example, is your dog or cat a tax-deductible emotional support animal? How would you deduct special needs education as a business expense? Can a health savings account turbocharge your retirement plan?

If you own more than 2 percent of an S corporation, you have to follow special rules to deduct your health insurance premiums. The health insurance rules can also apply to family members who work in the business and don’t own a single share of stock. Don’t let the zero stock be a surprise and cost your family money.

The Affordable Care Act’s $100-a-day penalty for improper medical reimbursements likely has your attention. It should. But you can find many reimbursements that are allowed without penalty, including the ability to reimburse Medicare when you have fewer than 20 employees.

You could qualify to use your swimming pool as a medical expense deduction just as Herbert Cherry did. Cherry deducted the cost of the pool to the extent it exceeded the increase in the value of his home. He also deducted the yearly cost of heating and insuring the pool, electricity for the pool room, and repairs for the pool room walls that suffered mildew damage.

The answer in this article explains how the S corporation can pay the solo owner-employee’s individually purchased health insurance without worrying about the $100-a-day penalty.

When you get busy with your business, it’s easy to forget about your retirement accounts and medical coverages and plans. But year-end is approaching, and now’s the time to take action. This article gives you six action steps for 2018 that can help you reduce your taxes and pocket extra money.

Your S corporation has to pay you reasonable compensation for the services you provide to the corporation. If your corporation pays your health insurance premiums, does that change the salary amount you need to pay yourself? We’ll tell you the answer and how doing it wrong would cost you money.

Are you confused by the tax deductions you can claim for your small-business health care? We can help you with our bird’s-eye view. It takes less than two minutes.

More than 2 percent shareholder-employees of S corporations don’t catch a lot of breaks when it comes to the taxation of fringe benefits. But arming yourself with the correct information will help you maximize your deductions and avoid costly penalties.

In IRS Notice 2015-17, the IRS allowed S corporation owners in 2014 and 2015 to avoid the $100-a-day penalties on S corporation reimbursements of individually purchased health insurance and on providing insurance for the owners only. But 2016, 2017, and 2018 are new years, so what is that status now?

Health savings accounts (HSAs) have gained substantially in popularity since enactment of the Affordable Care Act. Tax-wise, the HSA has some great features such as tax-deductible contributions, tax-deferred (even tax-free if used correctly) growth, and possible retirement benefits.

Looking for that extra boost to your retirement savings? Your first thought may have been to contribute to a traditional IRA. But before you do that, we have something else to show you. Consider a health savings account (HSA). That’s right. An HSA can be more than just funds you set aside to cover those copays. This is one surprisingly powerful savings tool that provides a much-needed boost to your retirement savings. See why an HSA provides some big benefits you won’t get with a traditional IRA.

The 105-HRA is the medical reimbursement plan you likely want to use if (a) you report your business income and expenses on Schedule C of your Form 1040 and (b) you can make your spouse your one and only eligible employee. Also, if you are single and operate your business as a C corporation, and if you are the one and only eligible employee of your C corporation, the 105-HRA is the medical reimbursement plan for you.

If you receive an award or settlement due to an injury claim, the law allows you to exclude some or all of the money you receive from taxation. You can use this exclusion along with other tax reduction strategies to minimize any tax you must pay on the amount you receive.

Sending a child to a special needs school can be an onerous financial burden, with some tuitions reaching even $100,000 per year. Tax law lets you deduct tuition and other related costs as medical expenses, but you need to know which expenses qualify and how you should deduct them. This article shows you not only how to qualify but also a possible best way to maximize those deductions.

Finally, the health insurance rules that apply to small businesses that want to provide medical benefits to their employees make more sense and allow some benefits. As you would expect, the new rules are not perfect. After all, this is tax law. But the new rules are light-years ahead of the old rules.

Do you have fewer than 50 employees? Are you in compliance with the Affordable Care Act? Whether you are in compliance or not, we may have some big news for you. First, if you failed compliance, a new law has likely just released you from the monstrous $100-a-day penalty ($36,500 per employee per year). Second, if you made changes to get into compliance, you may have overtaxed your employees. Now, with this new law, you may be able to undo some or all of that overtaxation.

When you get busy with your business, it’s easy to forget about your retirement accounts and medical coverages and plans. But year-end is approaching, and now’s the time to take action to cut your 2016 taxes. This article gives you six action steps for 2016 that can help you reduce your taxes and pocket extra money.

If you struggle with depression, anxiety, or other mental disabilities, you may rely on an animal for critical emotional support. But this support animal might do even more for you. It could qualify as an animal for which you can deduct its cost, training, and maintenance.

In IRS Notice 2015-17, the IRS allowed S corporation owners in 2014 and 2015 to avoid the $100-a-day penalties on S corporation reimbursements of individually purchased health insurance and on providing insurance for the owners only. But 2016 is a new year, so what is that status now?

Schedule C business owners and their spouses must obtain health insurance coverage for themselves (and any other dependents) or risk a penalty under health care reform. While there are many ways to get that coverage, one way—a properly established proprietorship reimbursement arrangement—can lead to three and possibly four significant tax advantages for the business owner and spouse.

You might want to tap your IRA penalty-free for medical expenses. If so, avoid the three traps that we explain in this article. Don’t be a victim. You suffer first because you incurred medical expenses, then you have to pay income taxes on the withdrawal of money from your traditional IRA, so the last thing you want is to pay a 10 percent penalty on top of all that.

The self-employed health insurance deduction could give you a big surprise when you file your taxes—and that’s not good. The law imposes a couple of restrictions that many people don’t know about and that might strip you of your tax savings. Take some time right now to figure out whether you qualify for the deduction and if not, what you can do about it.

You can protect yourself against the financial consequences of chronic illness or disability by purchasing long-term care insurance. The premiums for this insurance are not cheap, but tax law lets you write off the cost, thus subsidizing your purchase. But beware—there are three ways to take this deduction. Choosing the wrong method could cost you thousands of dollars in tax benefits.

If you are an S corporation owner, you can get a full deduction for your health insurance premiums—despite Obamacare and even if your S corporation provides zero health benefits to non-owner employees. You have to follow a few steps to qualify for this deduction, but that’s a piece of cake once you know the rules.

Have you been longing for the good old days when you could offer a Section 105 health plan to your employees without having to comply with the new Obamacare rules? Well, you can still offer such a plan—provided that you limit the benefits to vision and dental.

The IRS just launched its latest attack on your reimbursements for individually purchased health insurance: Even fully taxable reimbursements could still violate the Obamacare rules and expose you to the $100-per-day penalties. But don’t worry. We’ll give you several strategies to beat this new rule.

Whether or not you complied with Obamacare last year, we have some big news for you. It’s no problem, compliance or not, and either way the news is big for two reasons. First, if you failed Obamacare compliance in 2014, the IRS likely just released you from the monstrous $100-a-day penalty. Second, if you did it right, you may have overtaxed your employees and now, with the new IRS guidance, you can undo that overtaxation.

A November 2014 FAQ from the Department of Labor created quite a scare for S corporation owners, raising the possibility of huge Affordable Care Act (ACA) penalties simply for deducting your health insurance premiums according to IRS guidelines. However, a recent IRS notice explains how you can now safely avoid these penalties and claim your rightful deductions.

If you discriminate when you contribute to the health savings accounts (HSAs) of your employees, the IRS will make you pay a 35 percent tax on the total amount of your contributions. This tax can add up quickly, and if you have to pay it, you’ll kick yourself when you discover you can escape the tax entirely by following the three rules in this article.

If your doctor recommends that you buy equipment for your health, pay attention. First of all, you should follow your doctor’s orders. But just as important, you may be able to deduct some or all of the cost. This article explains how the one-owner businessperson is in the best possible position to deduct the cost of medical equipment.

If you are a regular reader of the Tax Reduction Letter, you know that you can use a Section 125 plan to save money on group health insurance. A number of subscribers have requested a template for how to set up one of these plans, and that’s what this article is all about—we’ll help you get your plan up and running.

Would you like to avoid payroll taxes on your S corporation’s inclusion of the cost of your health insurance on your W-2? You can. First, you and your S corporation can take advantage of one of two safe harbors. If you don’t qualify for a safe harbor, you can go back to a law originally enacted in 1939 and claim that you are in a separate class of employee exempt from payroll taxes on the health insurance fringe benefit that your S corporation gave you. And then if all else fails, you can pull out the IRS’s own publication and its online assistance and insist that the IRS follow them, even though they’re legally incorrect.

This article gives you a bird’s-eye view of the new health care landscape so that you can see all your post-Obamacare health care options together in one place. Choose the health plan that works best for your business based on the number of employees you have and the amount of money you are willing to spend.

As you know, Obamacare has a dramatic impact on Section 105 medical plans that cover more than one employee. Of course, the first question is who is an employee for purposes of the Section 105 medical plan. And if you have multiple employees, you will be happy to know that this article gives you eight strategies for making the 105 plan work for you.

If you are an S corporation owner and you buy health insurance for yourself or your family, you need to follow the IRS rules described in this article in order to protect your tax deductions for the health insurance premiums. You also learn how to escape the Obamacare penalties for group health care even if you discriminate against your employees.

If you want to cover your employees with group health insurance but worry that the price tag will skyrocket your budget, you need to read this article. You will learn how to limit your annual cost and provide tax breaks to employees for their share of premiums. By following some or all of the strategies, you can drop your after-tax cost of group health insurance coverage.

Do you employ 50 or fewer employees? Are you looking to do something on the health care front, but not interested in the group health insurance option? Health savings accounts (HSAs) could be exactly what you are looking for, especially as Obamacare becomes law.

In this article, you’ll learn how to create and/or ensure medical and retirement deductions before December 31. Of course, you need to get busy now. There’s not much time left. And if you are one of the targets who’s now subject to the new, higher tax rates that apply in 2013, you will find year-end planning more beneficial than ever.

The flow chart in this article helps you visualize what needs to happen at the S corporation for the owner-employee to get any tax benefit from health insurance. The tax rules are not what you would call logical, but the flow chart clarifies the rules and gives you the path to follow to ensure your tax deductions.

When you operate your business as an S corporation, you run into some weird tax-deduction rules, like those that apply to health insurance. For example, the S corporation may not deduct the cost of your health insurance as an employee-owner fringe benefit. Then, if you pay for the health insurance personally, you may not personally deduct the cost of the health insurance as a self-employed individual. Tax law has you in a classic catch-22. But there is a workaround that’s very straightforward and beneficial as described in this article.

The IRS just released the new 2013 standard mileage rates. For business purposes, you can use the standard mileage rates in lieu of actual expenses for depreciation and operating expenses of the vehicle. It’s different for charity, medical, and moving mileage. Here, the rate is in lieu of “out of pocket” operating expenses only.

In this article, you’ll learn four tax-planning strategies for your medical deductions and two strategies for your retirement. If you want to implement the strategies for 2012, you need to get busy now. There’s not much time left, and one of these strategies requires action before December 1.

If you operate your business as a proprietorship, S corporation, or single-member LLC, the HSA gives you, the owner, the ability to discriminate in benefits on your behalf. In addition, you get the HSA’s front-end tax deduction, tax-deferred growth, and no taxes on withdrawals used for medical expenses.

Because you are in business, you likely have the opportunity to improve your tax deduction for long-term care insurance. In fact, you might achieve a 100 percent deduction. If you are married, the 100 percent deduction can include your spouse.

To know if the S corporation is the best choice of entity for your business, first you need to consider three advantages and nine disadvantages. Next, you need to take the S corporation advantages and disadvantages that apply to you and get a bottom-line number comparison with your second choice for an operating entity. In this way, you can make a logical choice, knowing that your best choice will stay with you for a number of years and let you pocket more after-tax cash while you sleep better at night.

When you and/or your spouse own more than one business, you must look at all businesses as one business when applying the Section 105 medical reimbursement plan discrimination rules. If you are blocked by the discrimination rules, consider discriminating in health insurance coverage to your benefit.

The IRS admits that its regulation that made the single-member LLC a corporation for payroll tax purposes is unfair to small business family employment. To right this wrong, the IRS allows the single-member LLC to use the family employment rules to exempt FICA and Medicare taxes retroactively to January 1, 2009. The regulation granting this change expires on or before October 31, 2014.

In the right circumstances, the single-member limited liability company (LLC) gives you corporate liability protection combined with easy Schedule C (proprietorship) rules for your tax return. In this article, you learn the two tax advantages and two tax disadvantages to the single-member LLC.

Tax law makes it hard for the owner of an S corporation to win deductions for his health insurance. First, the corporate-provided health insurance is not a tax-free fringe benefit for the owner. Second, the S corporation has to pay for the health insurance or the owner will suffer a loss of tax deductions. Third, the S corporation payment for the health insurance will produce wages either exempt or nonexempt from FICA and Medicare taxes. This article shows you how to make the three tax deduction rules work for you.

With proper planning, you can use two exceptions to add a Section 105 plan, FSA, or HRA to your HSA.

The IRS changed its 1040 instructions to allow the proprietorship and single-member LLC a self-employed health insurance deduction for Medicare Part B. The impact on the S corporation owner is not as favorable.

The new under-age-27 health insurance coverage grants windfalls, pitfalls, and planning opportunities.

Tax law creates trouble for selected fringe benefits that the S corporation gives to a more than 2 percent shareholder. The loss of benefits and accompanying complications are factors to consider in the selection of the S corporation as your choice of business entity.

As a business owner, you should have your health insurance in a tax-advantaged position. If it is not possible or practical to utilize the Section 105 medical reimbursement plan, consider the health savings account.

Here is the big picture on how the health savings account (HSA) works for the proprietor, S corporation owner, and C corporation owner. The good news is threefold: (1) the tax deduction for the high-deductible insurance, (2) the tax deduction for the HSA investment account, and (3) the tax-deferral and tax-free use of the HSA investment account.

You need time and rate of investment return on your side to make your HSA investment grow to your satisfaction. One consideration for a higher rate of return is a self-directed HSA that allows you to invest in individual stocks, real estate, and mortgages.

You need to strategize your purchase of high-deductible insurance to maximize your HSA tax-favored investment portfolio.

The health savings account (HSA) offers the opportunity to save on insurance costs and create an investment nest egg. To learn how the HSA could work for you, do some easy arithmetic, like we show you in this article.

New guidance from the IRS on the new health care law says the owner of a business (proprietorship, corporation, LLC, etc.) may not claim the 35 percent tax credit on the health insurance premiums paid to cover his or her spouse.

When the S corporation makes HSA contributions on behalf of its more than 2 percent shareholder-employee, the S corporation treats the contributions as compensation to the shareholder-employee. In turn, the shareholder-employee has a deductible HSA on his or her personal tax return.

The Small Business Jobs Act of 2010 spends $12 billion on small businesses, hoping to add a little stimulus to this economy. Make sure you are getting your fair share of this stimulation.

Many one-owner and husband-and-wife-owned businesses opt for discriminatory health insurance plans for their businesses. The new health care law eliminates that discrimination for new plans but allows grandfathered plans to continue as before.

Tax credits are a true incentive for the business owner. They reduce taxes dollar for dollar. Now, you have waiting for you a hefty 35 percent tax credit on small-business health insurance coverage for employees. Here are the rules you need to know.

The new health care law grants a nice tax credit to business owners who cover their employees. How about the owners themselves? Lawmakers did them no favors, but one group of proprietors might catch a break.

For business owners who have children ages 22, 23, 24, 25, and 26, the new health care bill contains a healthy break, and perhaps even better than that. Amend Section 105 plans now for this new provision. Download your sample plan from this article.

Most of this issue explains how you pocket money from the new health care tax credits. That’s nice. But you have to ask, who is paying for my tax credits?

Make sure you know all of the ramifications of a premature IRA withdrawal before you make the withdrawal for medical expenses.

The S corporation owner is an employee of his or her corporation. Thus, his or her personal payment of health insurance does not qualify for deduction on page 1 of the Form 1040. To get this page 1 deduction, the IRS says that the health insurance must be paid by the corporation and come to the owner on a W-2.

Under tax law, Medicare B can be deducted as health insurance. We have proof. Also, we show you how to get the Medicare premium to qualify as an employer plan, and how to relate it to the earned income of your business.

Section 105 uses a definition of medical that is broader than that for an itemized deduction. This broadening allows you to deduct supplements and over the counter drugs to treat injuries and illness.

With one exception, you may not deduct a facelift as a medical expense because you use your face for both business and personal purposes. As to deducting the facelift as a business expense, this has not worked out so far.

A new 2006 law allows a one-time transfer of money from your IRA to an HSA. If you do it right, you can avoid income taxes or penalties. We’ll show you how.

You might be able to deduct Medicare payments as medical insurance premiums, but it depends which type of Medicare you have.

Take it from Richard Cotler: if you operate as a corporation, make sure to keep your personal and corporate expenses separate. Asking a court of law to separate your personal and business expenses is an expensive and time-consuming task. And you absolutely should keep the personal expenses clearly identified or, better yet, not on the corporate books at all.

Meal replacements, diet foods, and dietary supplements are substitutes for the food individuals normally consume, making them nondeductible personal expenses.

An inversion table lets someone hang upside-down by the ankles to alleviate back pain. According to tax law, it can be deducted as a medical expense.

You probably should not try to deduct teeth whitening. The law generally disallows a teeth whitening–type of expense because it has both a personal and a business benefit.

Deducting a piece of furniture, like a back chair, is tricky. You can do it, but you have to be very precise. For example, we recommend supporting your position by getting a prescription, and building proof that this chair would not be used generally as an article of furniture

The tax law allows you to deduct the cost of laser eye surgery, as long as it produces a business benefit. There are specific details that apply, though, so read carefully.

You get no business benefit from the section 105 plan at the S corporation level. However, you do get a big personal benefit when you steer the medical insurance through the S corporation to give yourself the medical insurance as a guaranteed payment.

Many S corporation owners are improperly deducting their health insurance on page 1 of the 1040. The American Institute of CPAs submitted a proposed revenue ruling that it would like the IRS to issue concerning health insurance for the S corporation owner. The proposed revenue ruling does nothing to alleviate the problem in the headliner; instead, it would formalize the problem.

Good tax planning for a trip to the medical doctor includes making a properly-targeted business stop the primary purpose of the trip.

When designing the medical plan, you need to consider all your and your spouse’s proprietorships, LLCs, and corporations as one business. If employees exist in one of these businesses, you have employees in all businesses. Plan your discrimination or nondiscrimination accordingly.

The more than 2 percent owner of an S corporation may not benefit from a fringe benefit like corporate paid health insurance. Further, this owner-employee is not “self employed” for purposes of deducting self-employed health insurance on page 1 of IRS Form 1040. This leaves the more than 2 percent owner with only one IRS approved method for gaining the maximum deduction from health insurance.

In Chief Counsel Advice, the IRS clarified its position that a sole proprietor may deduct the cost of health insurance on his or her Form 1040 regardless of whether the insurance is purchased in the individual’s or the proprietorship’s name.

The physician’s prescription often justifies a tax deduction, but not always. There are tax principles involved that need alignment for the deduction to prevail.