Understanding health insurance deductions and FSAs

Taxes: Healthcare

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Investments: Taxes

IRAs and Retirement Plans: IRAs and Taxes

Can I Deduct COBRA Insurance Premiums?


"My husband took early retirement. Then his old employer told him he could work just enough hours to pay for the COBRA insurance. So they will issue him a check each week minus deductions, then we will pay the COBRA ourselves. It will cost $1,102 each month. Is this going to be a tax deduction at the end of the year? "

Deduct Health Insurance Premium?


The Small Business Jobs Act made a sole proprietor's health insurance costs more in line with corporate-sponsored plans. Under the SBJA provisions, a Schedule C filer gets to reduce self-employment income by the amount of deductible heath insurance premiums paid during the year.

FSA Saves Money, Cuts Taxes


Workplace benefits can not only provide you and your family with much-needed services, but some of them also can help cut your federal tax bill. One of the most popular benefits is a flexible spending account, often referred to as an FSA. As helpful as these accounts are, they have one big drawback: the use-it-or-lose-it requirement that costs workers millions of dollars each year.

Reduce Your Medical Bills with an FSA

Josh Wozman

Flexible spending accounts allow employees to set aside a certain amount of each paycheck into an account in pretax dollars. During the year, participants have access to this account for reimbursement of medical expenses not covered by insurance, such as health insurance co-pays or necessary medical products.

Maximizing Your Medical Deductions


Medical costs seem to increase every year. There is a way to get Uncle Sam to foot some of the doctor bills, but you need to make sure you know and follow the rules.

Are Health Insurance Premiums Tax-Deductible?


"I took early retirement from my past employer and took the option of keeping the health insurance as a retiree. Are health insurance premiums tax-deductible? It is really good insurance, better than what I can get at my current employer, and it's available to me at the retiree rate as long as I live."

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