Core Insights - Roth conversions are viewed as a financially advantageous strategy, often recommended by financial advisors and framed as a tax-saving method [1] - The effectiveness of Roth conversions depends on various factors, including current and future tax brackets, longevity, and market performance [2] Retirement Length - The upfront tax paid during a Roth conversion must be offset by the growth of the converted assets over time [4] - Many financial advisors assume a 30-year retirement period for the strategy to be beneficial, but actual retirement lengths may be shorter, impacting the potential payoff [4][5] Tax Trade-Off - The primary assumption of a Roth conversion is that paying taxes now will prevent higher taxes in retirement; however, a high current tax bracket may negate the benefits of this strategy [6]