Conversion windows

Convert by the dollar, not by the slogan

Ivory Plains prints a Roth conversion schedule sized to your federal brackets, IRMAA tiers, and the December 31 cutoff that cannot be walked back in January. Each line is a tax year and a dollar amount. You instruct the custodian yourself. No AUM. No discovery call. Support is support@ivoryplains.com.

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Related plan pieces

Income plan by year

What arrives each year, and which account it comes out of, through the first required distribution.

Conversion schedule

Year-by-year amounts that fill a bracket without crossing a Medicare surcharge tier.

Withdrawal order

Which account funds which year, so the tax bill is a decision.

Dated deadlines

Enrollment windows, lookback years, and December 31 cutoffs with your dates on them.

How each dollar on the schedule is chosen

Send pre-tax balances and expected income by year after checkout. Open the tabs for how bracket math, IRMAA lookbacks, the December cutoff, and the RMD cliff shape each dollar on the schedule. You move the money with your IRA or 401(k) custodian before December 31 of each listed year.

Fill the bracket, year by year

Year 1. Measure wages, Social Security (if any), pension income, and planned taxable draws. Size the conversion to fill the remainder of the target federal bracket and stop before the next IRMAA tier that would price Medicare premiums two years later.
Year 2. Recompute room after the prior conversion lands on the return. Adjust for any claim-date change, bonus, or capital gain already booked. Print the new conversion amount beside the premium year it will influence.
Year 3. Check whether delayed Social Security or a pension start has consumed bracket room. Reduce or pause the conversion if the tax and IRMAA cost exceeds the Roth benefit for this household.
Year 4 and later. Continue only while pre-tax balances and RMD timing still justify the tax paid now. When the model says stop, the schedule ends with zeros, not with a standing instruction to convert every year.

This year-by-year list is the conversion schedule in plain form. Ivory Plains does not tell you to convert when you can. It names the years, the dollars, and the reasons the amount changes. You move the money with your IRA or 401(k) custodian before December 31 of each listed year. The plan does not place trades for you and does not call the custodian on your behalf.

If Plan and year or Household updates your facts, the year rows recalculate. The one-time Plan product does not keep an open conversion loop after delivery.

The two-year IRMAA lookback

IRMAA does not care that your conversion felt tax-efficient in the year you paid it. Premiums for Part B and Part D look back two years at modified adjusted gross income, and a conversion counts.

That lookback is why a conversion schedule without Medicare years is incomplete. A conversion in 2026 can change what you pay in 2028 even if you are still working, still delaying Social Security, or still drawing mostly from taxable brokerage. The plan prints both columns: conversion year and premium year.

Ivory Plains sizes each conversion against the IRMAA brackets in force for the premium year those dollars will hit. Crossing a tier by a small amount can cost more in premiums than the Roth move saves in later tax. Staying under a tier can leave unused bracket room that would have been cheap to fill. The schedule shows the trade in dollars, not in slogans about tax-free growth.

Married filing jointly and single filers do not share the same IRMAA thresholds. Household plans use the filing status you will actually use on the return that feeds the lookback. If one spouse enrolls in Medicare earlier than the other, the premium impact still follows MAGI on the joint return when you file jointly.

You enroll in Medicare and pay premiums through the government channels that apply to you. The plan's job is to make sure the conversion amounts you authorize do not surprise you two years later on a premium notice.

December 31 is not a soft target

A Roth conversion for a tax year must be completed by December 31 of that year. There is no recharacterization path that undoes a completed conversion the way older rules once allowed.
Custodians need processing time. A request submitted in late December can settle in January and land in the wrong tax year, or fail entirely if the firm is closed for the holiday week.
Employer plans may require paperwork, waiting periods, or in-plan Roth features that take longer than an IRA transfer. The plan flags that lag when your facts include a workplace account.
Estimated tax payments may be due during the year if the conversion creates a large balance due in April. The schedule notes when a mid-year payment is part of executing the listed amount.

Ivory Plains puts a processing buffer on the calendar so before year-end means a dated action with time left for settlement, not a reminder on December 30. Miss the cutoff and the next plan update can only schedule the following tax year. January cannot repair December.

You initiate the conversion with the firm that holds the account. The plan does not wire funds, does not open Roth accounts for you, and does not certify that a late request will post in time.

Shrink the balance before the RMD cliff

Required minimum distributions turn pre-tax balances into forced taxable income once you reach the applicable age under current law. The larger the balance, the larger those annual withdrawals. Converting before that age can shrink the mass the RMD formula later multiplies, which can lower future tax bills and reduce how much of Social Security becomes taxable under the combined income rules.

That is not an argument to convert everything at once. A single oversized conversion can push you through federal brackets and IRMAA tiers in the same year, then leave you with a tax bill that consumes cash needed for bridge years. The schedule spreads conversions across years where bracket room is cheap and RMD pressure is still ahead, then stops when further conversions no longer pay for the tax due now.

Ivory Plains ties conversion rows to the same income-by-year page that shows claim dates and withdrawal order. When Social Security or a pension starts, bracket room may vanish. When taxable brokerage can fund spending, you may preserve IRA room for conversions instead of spending draws.

Estimate pre-tax balances at the first RMD year under current law.
Project RMD amounts with and without the proposed conversion series.
Score tax and IRMAA cost of each conversion year against later RMD relief.
Print conversion dollars only for years where the net still favors the move.

You choose whether to follow the amounts. The plan's job is to make the trade visible before you instruct the custodian.

Conversion windows in depth

A Roth conversion is ordinary income in the year you convert. Done carefully, it fills remaining room in a federal bracket and stops before the next IRMAA tier that will price Medicare premiums two years later. Done carelessly, it buys a higher bracket this year and a higher Part B premium later.

Your schedule is a list of tax years and dollar amounts. Each line is sized to bracket room, IRMAA cliffs, pre-RMD shrinkage, and custodian timing. December 31 cannot be walked back in January. You instruct the firm that holds the account. Ivory Plains dates the work; it does not move the money.

Why multi-year beats opportunistic

One large conversion year can look clever until IRMAA and Social Security taxation interact. A multi-year schedule spreads the work, protects lookbacks, and shows what remains before RMDs force distributions. When wages end or claims start, update tiers rebuild the lines against the new income picture.

Bracket room is not a vibe

Ordinary-income brackets are statutory. Your conversion line is sized against them after the income you actually have. IRMAA tiers use a two-year lookback. Crossing a tier by a small amount can raise Part B and Part D premiums for a whole premium year.

Social Security taxation interacts with IRA draws and conversions in the same year. The schedule exists so those interactions are visible before you instruct a custodian. December 31 remains the hard stop.

Extended field guide: conversion windows that survive contact with the calendar

Roth conversion windows are not a mood about markets. They are dated amounts in dated tax years that must clear before ordinary income from wages, pensions, Social Security, and required distributions fills the same brackets. This guide sits beside the conversion schedule on your plan. It explains how windows connect to claiming and withdrawals, what input quality problems look like, what fails when you miss a year, how IRMAA lookbacks punish silent over-converting, and how tier choice controls whether you can rebuild when facts change. Ivory Plains does not manage assets and does not begin with a discovery call. You receive dated instructions. You instruct the custodian. Fees stay public: Plan $1,200 once; Plan and year $1,200 then $95 a month or $950 a year prepaid; Household $3,400 a year. There is no AUM fee and no mandatory discovery call. You file and instruct yourself. Questions about reading a page go to support@ivoryplains.com.

How this page connects to the rest of the ledger

A conversion schedule only works when the peer pages stay true. Ivory Plains delivers a dated system: claim months, conversion dollars by year, withdrawal sources by phase, and calendar deadlines. Changing one page in your head without rebuilding the others creates a plan that looks complete and fails in December.

Read claiming decisions first so you know when benefits start. Read withdrawal order next so spending does not force IRA income into conversion years. Read dated deadlines so custodian instructions settle in the intended tax year.

Claiming decisions set when Social Security income begins and when delayed credits stop
Conversion windows set how much ordinary income room each tax year still has
Withdrawal order sets which account funds spending without wrecking those years
Dated deadlines set the external clocks at SSA, Medicare, custodians, and the IRS

What a window actually is

A window is a tax year, sometimes a partial year, where projected ordinary income leaves room under a target bracket or IRMAA cliff for a printed conversion amount. Ivory Plains does not say convert what feels right. It prints dollars and years. You own tax withholding and estimated payments. The product boundary is deliberate: dated instructions, not discretionary management of a sleeve of IRA money.

Windows close for predictable reasons. Wages continue longer than you told the questionnaire. A pension starts. A spouse claims Social Security. RMDs begin. A large capital gain from selling a house lands in a year you forgot to disclose. Equity compensation vests. A side business produces more ordinary income than last year. Each of those is an input problem or a life change. Neither is fixed by staring at last year’s schedule and hoping the bracket math still holds.

Some windows are intentionally thin. A year with a partial salary and a first Social Security check may still support a small conversion that keeps a multi-year sequence alive. Skipping thin years because they feel unimportant often forces larger conversions later when RMDs arrive. The plan’s job is to show the thin year as a real instruction, not as optional homework.

Worked examples

Example A: dual delay to 70 with large traditional balances and modest brokerage. The plan may print aggressive conversions in the bridge years, funded by brokerage spending so IRA withdrawals are not also required. If you instead spend from the IRA because that is retirement money, you collapse the window you paid to design. The failure is behavioral, not statutory.

Example B: one early claim for cash flow, one delayed claim for survivor floor. Conversion amounts step down when the first benefit arrives. Missing that step-down and converting the old higher amount can push you across an IRMAA threshold. Two years later Medicare premiums rise and the household blames the plan instead of the skipped update.

Example C: Plan delivery at age 61, Rule of 55 workplace plan available, and a planned claim at 67. Conversions may be sized assuming workplace money covers spending. Leaving the job later than disclosed, or rolling the workplace plan to an IRA too early, removes Rule of 55 access and forces IRA income into conversion years. Rebuild when the job date moves.

Example D: a widow rebuilds two years after the original plan. Filing status, standard deduction, and survivor benefits change the bracket map. Reusing the old married-joint conversion schedule is a category error. Household or Plan and year exists so that rebuild is a product path, not a favor.

Project ordinary income for each year from wages, pensions, benefits, and planned withdrawals
Apply the target bracket and IRMAA constraints printed on the plan
Allocate conversion dollars to years with room
Check that spending is funded from accounts that do not wreck those years
Print amounts, years, and the assumptions underneath
Re-check after any material income or claim change

What fails if you miss a conversion year

Skipping a conversion year does not roll the dollars forward automatically at the same tax cost. The next year may include a benefit, a pension, or an RMD. Saying you will catch up later often means converting in a harsher bracket. Conversely, converting more than the plan printed because a market dip felt like a sale can spend bracket room the plan reserved for a later, more valuable year, especially a year just before RMDs begin.

Custodian timing matters. A conversion initiated in late December that settles in January is a next-year conversion. The dated deadlines page exists so you do not discover that in February. If you miss the deadline, do not invent a fix by converting twice as much the following week without checking the new year’s income picture. Correct course on an update tier if the miss is material.

Withholding mistakes are a second failure mode. Converting without setting aside cash for the tax can force an IRA withdrawal later that was not in the withdrawal order. That withdrawal then fills next year’s bracket and shrinks the next window. The conversion page assumes you can pay the tax from non-IRA cash unless your inputs said otherwise.

A conversion window is a dated budget for ordinary income. Treat it like a filing deadline, not like a newsletter idea.

Input quality and edge cases

State tax, NIIT exposure from investment income, equity compensation, rental losses that may not repeat, and charitable bunching all change available room. Enter them if they are real. Do not enter a charitable pledge you will not execute just to invent room. Do not hide a side business that will keep producing ordinary income. Ivory Plains will not discover your life in a sales call. The questionnaire is the discovery.

Backdoor Roth contributions, mega backdoor workplace after-tax conversions, and QCD planning can interact with the schedule. When those apply, they belong in the file. When they do not, leave them out. Mixing a blog strategy into a dated ledger without inputs is how households double-count tax benefits.

Married filing separately, nonresident alien spouses, and community-property states create filing surfaces the model only handles when told. If your situation is unusual, put the unusual facts in writing in the questionnaire. Support can help you map a fact to a field. Support will not invent a clean story to make the schedule prettier.

Tier choice for conversion maintenance

Plan at $1,200 once fits a household ready to execute a multi-year schedule with stable income assumptions. Plan and year exists because conversion capacity changes when markets, wages, and claims move; pricing is $1,200 then $95 a month or $950 a year prepaid. Household at $3,400 a year is for broader ongoing coordination. None of these tiers is portfolio management. If you need the schedule rebuilt, change inputs and use the tier you bought (or upgrade) rather than editing PDF highlights with a pen.

Upgrade when you notice a persistent gap between the printed years and your real income. Do not wait until RMD year to admit the schedule is folklore.

Why the window matters

What the schedule shows

Year by year conversion amounts that fill a bracket without crossing a Medicare surcharge tier.

Until distributions begin

The window closes the year required distributions start. Conversions for a tax year must settle by December 31.

Fast Automation

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Bracket and IRMAA

Each line is an amount for a tax year, sized to the bracket and the IRMAA tier that prices two years later.

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