Is a Roth conversion always the right move? For many households, prepaying taxes can be a costly mistake due to negative tax arbitrage. Large conversions can also trigger hidden penalties like the Medicare IRMAA cliff, Social Security tax torpedo, and ACA subsidy losses. Learn when to pause a conversion and discover superior, tax-free alternatives like Qualified Charitable Distributions (QCDs) and Donor-Advised Funds to maximize your lifetime after-tax wealth.