https://www.live-feeds.com/feed/the-roth-conversion-deadline-is-dec-31-but-the-tax-bill-comes-due-jan-15-retirees-who-don-t-prepay-get-hit-with-a-penaltContinuously updated, source-cited coverage. https://www.live-feeds.com/feed/the-roth-conversion-deadline-is-dec-31-but-the-tax-bill-comes-due-jan-15-retirees-who-don-t-prepay-get-hit-with-a-penalthttps://www.live-feeds.com/feed/the-roth-conversion-deadline-is-dec-31-but-the-tax-bill-comes-due-jan-15-retirees-who-don-t-prepay-get-hit-with-a-penalt#u53291Tue, 01 Sep 2026 00:01:05 +0000Retirees converting traditional IRAs to Roth accounts must meet a December 31 deadline, with tax payments due by January 15. Failure to prepay these taxes can result in penalties. Additionally, each conversion triggers a unique five-year clock; withdrawing funds before this period expires may incur penalties on money intended to be tax-free. While some retirees use annual conversions to access funds early without penalties, others may reduce their tax burden by converting assets during down-market years when share values are lower.Why it mattersRoth conversions shift assets from tax-deferred t