Types

• Self-employed people can deduct half their insurance premiums from their adjusted gross income, in most cases. People that receive health coverage from employers can include the amount they pay in their itemized deductions.
  
  

Size

• If your premiums and all medical expense don't total more than 7.5 percent of your income, you can't deduct the premiums in the itemized expenses, whether you are filing as single, married or head of the household.
  
  

Considerations

• Self-employed individuals can take half their health premiums off their income in most cases, if they had a net profit. However, if they are eligible for insurance subsidized by a spouse's employer, they cannot take off half the premium. If they were eligible in only some months, they cannot deduct half the premium for those months.
  
  

Cafeteria Plan

• Health insurance premiums aren't deductible if they're part of a cafeteria plan paid with pretax dollars. In essence, you'd be deducting money that had never been taxed.
  
  

Itemized Deductions

• Even if your health insurance and medical expense was more than 7.5 percent of your gross income, you still might be wise not to itemize if the deductions aren't as much as the standard deduction. For single or married filing separately, it's $5,700. The amount is $11,400 for married filing jointly or qualifying widow(er) and $8,350 for head of household.