I'm 58 and still working. Is now a good time to start converting some of my IRA to a Roth?

It can be, depending on your tax situation. The key question is whether the rate you would pay today on a partial conversion is likely lower than the rate you will face on required minimum distributions starting at age 73 (or 75 if you were born January 1, 1960 or later). If you have a large traditional IRA balance and are currently in a moderate bracket, converting in measured annual amounts while still working can smooth your lifetime tax exposure and permanently reduce future RMD obligations. The right amount depends on your current bracket, projected future income, Medicare thresholds, and California's tax treatment of conversions.

 I just retired at 62 and my income dropped significantly. I heard this could be a good window for Roth conversions. Why?

This is one of the most widely missed planning opportunities in early retirement. The years between stopping work and the start of Social Security and RMDs are often your lowest-income years. During this window you may be in a lower marginal bracket than you will be once those income sources begin. Converting IRA funds to a Roth during this period means paying tax at a lower rate today in exchange for tax-free growth and tax-free distributions later. It also permanently reduces the balance subject to RMDs, which are fully taxable as ordinary income. For many people in the 60-to-70 age range, systematic Roth conversions represent the highest-impact tax planning move available.

 Why is the window before RMDs begin so important for Roth conversions?

At the RMD starting age (73 for those born 1951 to 1959, and 75 for those born January 1, 1960 or later), the IRS requires a minimum annual withdrawal from your traditional IRA. The RMD amount itself cannot be converted to a Roth; it must be distributed first, and only amounts above the RMD can be converted in the same year. For people with large IRA balances, RMDs can push them into higher tax brackets, increase the taxable portion of Social Security, and trigger Medicare IRMAA surcharges. Every dollar converted before the RMD age is a dollar that will never be forced out as taxable income. This is why the years between retirement and the RMD starting age are the most valuable conversion window for most people.

 How much should I convert to a Roth each year?

There is no single formula, but the most efficient approach is to convert up to the top of your current tax bracket each year without crossing into the next one. For example, if you have room in the 22% bracket before reaching the 24% threshold, filling that space annually over a decade can be a sound strategy. The exact amount also depends on your other income sources, your Medicare premium thresholds, California's ordinary income tax on conversions, and your projected RMD amounts. A good conversion plan models this annually and adjusts based on your actual year-end income rather than using a fixed dollar amount every year.

 What is the difference between contributing to a Roth IRA and doing a Roth conversion?

A Roth IRA contribution is money you put in from earned income, subject to annual limits ($7,500 in 2026, or $8,600 if you are 50 or older) and income eligibility limits. If your income exceeds the threshold, you cannot make a direct Roth contribution. A Roth conversion is different: you move money from an existing traditional IRA into a Roth IRA, paying income tax on the converted amount that year. There are no income limits and no annual dollar limits on Roth conversions. The two strategies can be used simultaneously, and conversions are particularly valuable for people whose income is too high for direct Roth contributions.

 I'm worried that a Roth conversion will raise my Medicare premiums. Is that a real concern?

Yes. IRMAA (Income-Related Monthly Adjustment Amount) is a real planning variable. Medicare Part B and Part D premiums are based on your modified adjusted gross income from two years prior. A conversion that raises income above an IRMAA threshold can result in significantly higher Medicare premiums two years later. This does not mean avoiding conversions; it means sizing the annual conversion amount with IRMAA thresholds explicitly in mind. Coordinating Roth conversions with Medicare planning is a standard part of the annual planning work we do with clients.

 My spouse passed away recently. Does that affect whether I should do Roth conversions?

Yes, and this is one of the most time-sensitive planning issues following the loss of a spouse. In the year of your spouse's death you can generally still file as married filing jointly. Beginning the following year you file as single. Single tax brackets are approximately half the width of married filing jointly brackets, meaning the same income can push you into a significantly higher marginal rate. For surviving spouses with large traditional IRA balances, future RMDs will carry a higher tax cost under single filing status. Doing accelerated Roth conversions in the year of the spouse's death, while joint filing is still available, can permanently reduce that future liability. This analysis is time-sensitive.

 I'm 68 and haven't done any Roth conversions yet. Am I too late?

Not at all. If your RMD starting age is 73 or 75, you may still have several years of meaningful conversion opportunity. The right question is whether converting a portion of your IRA today, at your current rate, is better than taking larger RMDs later at potentially higher rates. For someone with a significant traditional IRA balance and moderate current income at 68, the case for systematic conversion is often still strong. A forward-looking tax projection will show whether conversion makes sense and at what pace.

 Is there any downside to Roth conversions?

Yes. You pay tax today in exchange for tax-free distributions later, which requires having money outside the IRA to pay the conversion tax (using IRA funds reduces the benefit). Conversions raise your current-year income, affecting Medicare premiums, the taxable portion of Social Security, and eligibility for income-based programs. If your retirement tax rate turns out significantly lower than expected, you may have overpaid. The decision should always be based on a full annual tax projection, not a general assumption that conversions are always the right move.

 I keep hearing about a 5-year rule on Roth IRAs. What exactly is it and are there really two different rules?

There are 2 separate 5-year rules for Roth IRAs, and they serve different purposes. Confusing them, or knowing only one, is one of the most common Roth planning mistakes.

 The first 5-year rule governs whether earnings inside a Roth IRA can be distributed tax-free. For earnings to come out tax-free (not just penalty-free), the account must have been open for at least 5 tax years. The clock starts on January 1 of the first year for which you made any Roth IRA contribution or conversion, regardless of when during that year the money actually went in. This clock applies collectively across all of your Roth IRAs, not per account. Once satisfied, it is satisfied permanently. Your original contributions can always be withdrawn tax-free at any time since you already paid tax on them.

 The second 5-year rule applies specifically to Roth conversions. Each conversion has its own 5-year clock. If you withdraw converted funds within 5 years of that conversion and you are under age 59.5, the converted amount is subject to a 10% early withdrawal penalty. Once you are 59.5 or older, the second rule no longer creates a penalty exposure, though it still affects the ordering rules that determine which funds are considered distributed first. This rule exists to prevent people from using Roth conversions as a backdoor way to avoid the 10% early withdrawal penalty on IRA distributions.

 I've been doing Roth conversions since I retired at 62. I'm now 65. Can I access the money I converted 3 years ago without any tax or penalty?

At 65, the 10% early withdrawal penalty no longer applies to you regardless of when conversions were made, since you are past age 59.5. The second 5-year rule (the one applying to conversions) is therefore no longer a penalty concern. The first 5-year rule, the one about earnings being tax-free, still applies if your Roth IRA is relatively new. If you opened your first Roth IRA with a conversion in 2022, the 5-year clock runs through January 1, 2027. Earnings withdrawn before that date could be taxable even though you are past 59.5. The converted principal itself can be withdrawn without tax or penalty at any time since you paid income tax on it at conversion.

 The practical takeaway at 65: the penalty risk is gone. The only remaining tax risk involves earnings from a newly opened account, and only until the 5-year clock is satisfied.

 I'm 71 and just opened my first Roth IRA through a conversion. Will I have to wait 5 years before the money is available to me tax-free?

The 5-year clock for the earnings rule applies regardless of age, including at 71. Since this is your first Roth IRA, the clock starts January 1 of the year the conversion was made. Earnings withdrawn before 5 tax years have passed could be taxable even though you are past 59.5 and subject to no penalty. The converted principal can be withdrawn without tax at any time since you paid income tax on it at conversion.

 As a practical matter, most people doing Roth conversions in their early 70s are not converting primarily to spend the money immediately. The value of conversion at that stage is typically tax-free growth for heirs, reduction of the taxable IRA balance subject to RMDs, or building a tax-free reserve for future large expenses. In those scenarios, the 5-year waiting period for earnings rarely creates a meaningful planning problem. If near-term access to the funds is a priority, that should be factored into the timing of when to open and fund the account.