This study delves into how the timing of income taxes—either immediately on contributions to Roth accounts or deferred to the time of distribution from traditional accounts—affects retirement investment decisions. Individuals’ financial security in retirement often hinges on their participation in defined contribution plans (e.g., 401(k), IRA), and their ability to live comfortably in retirement further depends on making prudent investment selections long before leaving the workforce. Though conventional wisdom suggests investors should seek more volatile investment vehicles (e.g., stocks) earlier in life while gradually shifting to more stable investments (e.g., bonds) closer to retirement, this is often a struggle for people who are already resource-constrained and averse to such risk.