You're in Vegas, baby, and the cherries line up to dump a windfall in your lap. And now, you've got plans: a fantasy trip to the Galapagos, a spa renovation for your bathroom and that overpriced luxury item you so richly deserve. But before you can spend your winnings, Uncle Sam comes a-knockin' with a hand outstretched.

Even if you don't win a small fortune at the slots, there are surprising avenues through which Uncle Sam can stake a claim on your extra cash. Unfortunately, uncommon money often means unforeseen taxes. Read on to find out what's taxable and what you can do about it.

TUTORIAL: Personal Income Tax Guide

Bosses and Bonuses: Employer Benefits
Any money that your employer gives you - be it a bonus, funds for tuition, or travel and moving expenses - may be taxable. Often, your employer will calculate and withhold the extra taxes for you, but that doesn't mean you won't be surprised by how much you pay. (To learn how to negotiate a bonus, read Negotiating Employment Perks.)

Your fat holiday bonus, for example, is not subject to the same tax regulations as your salary - it may be considered a supplemental wage, in which case it's taxed at a flat federal rate of 28%. You must also pay state and local taxes, as well as Social Security and Medicare. Thus, your $5,000 holiday bonus may amount to only $3,300 after the Internal Revenue Service (IRS) pockets 34% in taxes.

Now, if you earn a noncash award for service, you usually avoid taxes as long as you've been with the company for five years and the value of the award is below the current IRS annual limit on noncash awards: $1,600 for 2008. Thus, if you spend a decade at a magazine as a graphic designer and you receive a $1,000 diamond pendant for your 10 years of service, you won't be taxed on the value of that award. However, if the award for your hard work is a shiny new car (lucky you, if that's the case!), the value of that car above $1,600 is taxable. For a $30,000 car, you would pay taxes on $28,400.

With employer educational assistance, the regulations can get a little tricky. According to the IRS, you can exclude up to $5,250 of educational assistance, and "your employer should not include the benefits with your wages, tips, and other compensation . . . and you do not have to include the benefits on your income tax return."

However, if your employer is especially generous, perhaps helping you pay your way toward an MBA, your education benefits likely exceed $5,250, and you must pay tax on the excess. Again, your employer should include the taxable amount on your W-2. (Learn how to boost your value in the job market at your employer's expense in Tuition Reimbursement - An Employment Perk.)

But, here's the tricky part: excess benefits qualify as a working condition fringe benefit - that is, a benefit that you could deduct as an expense if you had paid for it yourself - then your employer does not have to include the benefits in your wages.

Work Swap: Bartering Goods and Services
The system of exchanging goods or services instead of money is officially known as reciprocal trade, and it is regulated: when you barter for business, you receive Form 1099-B and a copy is sent to the IRS. People often wonder whether bartering can help them avoid taxes, but in fact, the exchange is subject to the same rules as income.

Suppose that you approach your local veterinarian for a business trade: you swap your graphic design skills, creating brochures and a website, and in exchange you get exams and boarding for your Great Dane, Lulu. You and the vet must report the fair market value of the bartered services as income on Schedule C. That is, the vet reports the value of Lulu's boarding and exams as income to the IRS using form 1099-B; you receive a copy of this form and, in turn, report this amount on your tax return. Likewise, you would report the value of your graphic design services using form 1099-B, and the vet would declare the amount on his or her return.

Be aware that you may also have to pay estimated taxes on reciprocal trades. On the bright side, these exchanges can be tax deductible. In this example, the vet could deduct the value of your services because he or she will use your brochures for business, but you can't deduct Lulu's exams because they're not a business expense. You can, however, deduct any costs you incurred to perform the work you bartered. (For related reading, see Common Tax Questions Answered.)

Civic Centered: Jury Duty
The dreaded letter arrives in the mail, and you grudgingly carry out your civic obligation and report for jury duty. When you serve on a jury, the pay you receive from the government is reported to the IRS. So, if you fail to report that income, the IRS could send you a deficiency notice.

Most employers (but not all) will continue paying you while you serve on a jury, and some will request that you turn over your jury pay. If your employer demands your jury wages, you can claim an offsetting deduction on line 30 of Schedule C.

Luck of the Draw: Gambling Winnings
When you're lucky at gambling, the IRS is lucky, too. The IRS taxes gambling winnings at the highest rates allowed, so when you scratch that lottery ticket to reveal a cool half mil', don't call your boss and tell him where to stick his weekly reports - Uncle Sam takes 25% of your winnings, so you are likely to end up with much less than you think.

And don't think you can keep your windfall a secret - agencies that operate legal gambling programs - whether it's the Texas Lottery, Belmont racetrack or the MGM Grand - are heavily regulated, and they are required to report your winnings for you. (For further reading, see Winning The Jackpot: Dream Or Financial Nightmare?)

According IRS Publication 17, "Gambling winnings from bingo, keno, and slot machines generally are not subject to income tax withholding."

No Work, Still Taxed: Unemployment Income
Unemployment income: It sounds like an oxymoron, but if you lose your job, don't expect any breaks from the government. Unemployment compensation is a form of income, and it is taxable - the federal government will efficiently send you the appropriate form to ensure you give back part of the money your state's unemployment fund gives you.

Death by Taxes: Life Insurance
Beneficiaries of life insurance usually avoid taxes on the payout, but in some situations the policy can be taxed - the tax determination is based on how you structure the policy (which is beyond the scope of this article). Life insurance can be taxed in the following cases: if you transfer a policy for valuable consideration (that is, you take the cash value of the policy), if the policy was arranged without an insurable interest based on state law (that is, if you indicated no beneficiary), and sometimes when the policy is employer-owned. (For related reading, see 5 Mistakes That Can Ruin Your Life (Insurance) and Cashing In Your Life Insurance Policy.)

In addition, if you make a gift of your policy to a third party (except to your spouse), it can be subject to a gift tax - a tax you must pay. And, if you do not survive your gift by three years, the policy can be brought back into your estate and subjected to estate tax. For most folks, the estate tax is no concern, as average estates don't exceed the 2009 nontaxable limit of $3.5 million. However, if you carry large amounts of life insurance, the death benefit could push your estate over the $3.5 million threshold, and Uncle Sam will get 45% of any amount over that $3.5 million. (Learn how to lower your income tax and avoid estate tax in Cut Your Tax Bill With Permanent Life Insurance and Shifting Life Insurance Ownership.)

Taxes are a necessary evil: the government needs taxes to fund infrastructure, important social programs and expensive screwdrivers. Most of the avenues are available to you for extra income, however, there are also roads that lead to extra tax payments. So, when you get an unexpected check, check out the regulations that may apply. Find out when you'll be taxed and by how much, so you won't be surprised when Uncle Sam shows up to collect his share.

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