Roth Conversion Checklist 2026: 27 Steps for Annual Planning

Use this checklist each year to plan, execute, and report your Roth conversions correctly. Check off each item as you complete it — your progress saves in your browser so you can return across multiple sessions.

✓ Progress saved to your browser.

The December 31 conversion deadline means you need your income picture in hand by early fall. Most advisors recommend finalizing the conversion amount in October or November, leaving time to execute before year-end.

Common checklist mistakes

• Skipping the IRMAA lookback. You're optimizing this year's bracket while accidentally triggering a $2,000-per-spouse Medicare surcharge two years from now. The two-year lag makes IRMAA uniquely dangerous — check it first, not last.
• Withholding tax from the conversion itself. Every dollar withheld is a dollar that never entered Roth. On a $200K conversion at 24%, that's $48K of tax-free compounding permanently lost. Pay tax from outside funds.
• Converting before taking the RMD. If you're 73+, the RMD-first rule is absolute. Converting before satisfying your RMD is an excess contribution to Roth IRA — it must be corrected before the tax filing deadline or you face a 6% excise tax per year the excess sits.
• Not checking the ACA cliff. Pre-Medicare early retirees on Marketplace coverage face a sudden, complete loss of premium tax credits the moment MAGI crosses 400% FPL. The cliff is a hard stop — going $1 over can cost more than the tax savings from converting.
• Year-by-year bracket optimization without multi-year modeling. Converting to fill the 22% bracket every year sounds logical — but without seeing years 2-10, you may miss that delaying Social Security or a pension start would have reshaped brackets and allowed larger low-rate conversions earlier.

How this checklist connects to your golden window

Roth conversions create the most value when executed during the golden window — the years between retirement and RMDs when earned income is low and Social Security is often delayed. But the window isn't static. It changes as you move through the three phases (ACA coverage → Medicare → RMD active), as IRMAA exposure shifts, and as your IRA balance and projected RMDs evolve. Running this checklist each October gives you one annual decision point to recalibrate the plan, rather than letting a rigid annual conversion amount run on autopilot.

If you have a partner, coordinate jointly. Married-filing-jointly brackets provide more conversion room per dollar of baseline income than filing single — but the widow/single-filer cliff is real if one spouse dies. The married couples guide covers the widow bracket problem and how to front-load conversions to protect the surviving spouse's tax position.

1. IRS Rev. Proc. 2025-32 — 2026 tax bracket thresholds. IRMAA Tier 1: $109,000 single / $218,000 MFJ from CMS 2026 IRMAA fact sheet. ACA 400% FPL from HHS 2025 Poverty Guidelines.
2. IRS Publication 505, "Tax Withholding and Estimated Tax" — safe harbor rules and estimated payment deadlines. IRC § 6654 ratably-treated withholding.
3. IRS Form 8606 — Nondeductible IRAs (required for all Roth conversions to track basis and taxable amounts).
4. IRS Retirement Plans FAQ — IRA contributions and conversions. IRC §§ 408A, 408(d)(2), 72(t), 3405(c).

Values verified as of May 2026. IRMAA thresholds from CMS 2026 fact sheet; bracket thresholds from IRS Rev. Proc. 2025-32; ACA FPL from HHS 2025 guidelines.