@scotttiger - can you please post the link to the reference about medical premiums being "penalty free'?
https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-tax-on-early-distri...
yes, there is an exception to the 10% penalty for IRA withdrawals if you are unemployed, but "in a pinch", which could occur while employed doesn't satisfy the requirement. If the taxpayer is unemployed and has to pay the medical premium for their dependent, that appears to be acceptable.
And even if the 10% penalty is waived, the tax is not waived.
Look at the 2nd line marked 'Medical" at the link above
