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Yes, health insurance premiums that you pay out of pocket can be entered as medical expenses.
If you took money from a retirement account you will receive a 1099R ---sometimes they do not arrive until early February.
To enter your retirement income, Go to Federal> Wages and Income>Retirement Plans and Social Security>IRA 401 k) Pension Plan Withdrawals to enter your 1099R.
Yes. Health insurance premiums are considered medical expenses. If you are looking to avoid the 10% penalty on early withdrawal, it is helpful to remember that medical expenses must be greater than 7.5% of adjusted gross income to be counted.
You can read more about this topic here: An Early Withdrawal From Your 401(k): Understanding the Consequences
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