Yes the IRS matches the information filed to the information that is received directly from employers, pensions etc. It could possible trigger an audit.
Your retirement board informed you correctly that you can get a deduction for health insurance premiums as an itemized deduction.
You can usually deduct the premiums for short-term health insurance as a medical expense. Short-term health insurance premiums are paid out-of-pocket using pre-tax dollars, so if you take the itemized deduction and your total annual medical expenses are greater than 7.5% of your AGI, you can claim the deduction.
Well, if you take the standard deduction you do not receive that deduction specifically because the standard deduction is larger than your total itemized deductions.
The amounts listed on the form 1099R is for information purposes in preparing your tax return.
In general, §106(a) provides that gross income of an employee does not include employer-provided coverage under an accident or health plan. Under §106(a), an employee may exclude premiums for accident or health insurance coverage that are paid by an employer.
IRS PUB: Medical and Dental
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