10/15/2026
Timing a $100,000 Roth Conversion
One of the analytical puzzles I enjoy most with clients is identifying that narrow window after retirement—when your tax return is quieter, but before the flood of benefit income arrives—where a Roth conversion can make the most sense. For example, if you’re receiving a $45K pension and not much else, a $100,000 Roth conversion lands very differently than it would once Social Security and required withdrawals start piling on. Once those retirement benefits begin, the conversion can push your provisional income higher, making up to 85% of those benefits taxable—a shift that can quietly increase your total tax bill. There’s also the ripple effect: Medicare’s federal health program looks back two years, so a large conversion today could mean Part B and Part D premium surcharges down the road. In 2026, those surcharges began at $109K for single filers and $218K for joint, so timing a conversion could push you into higher premium tiers. I often find it’s worth comparing smaller, incremental conversions against a single large move, and weighing which year offers the least competition from benefits, surcharges, and required withdrawals. These are the moments where a methodical review—grounded in real-world experience—can make all the difference in achieving your long-term goals.