Deorbit Plan

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Short, practical explainers on Roth conversions, RMDs, IRMAA, ACA subsidies, and the other tax and Medicare rules that shape a retirement plan.

Tax mechanics

  • The Roth conversion ladder, explained

    How the 5-year seasoning rule, gap years, and fill-the-bracket conversions turn pre-tax savings into tax-free money — and why looming RMDs put a deadline on it.

    Last reviewed July 2026 · 5 min read

  • The three 5-year rules of Roth accounts

    Contributions, conversions, and inherited Roths each carry their own 5-year clock — which one starts when, which triggers taxes vs. penalties, and the withdrawal ordering that makes ladders work.

    Last reviewed July 2026 · 5 min read

  • Backdoor and mega-backdoor Roth — and the pro-rata trap

    How high earners fund Roth accounts past the income limits, why the IRS aggregates all your IRAs when you convert, and the 401(k) features that unlock up to $72,000 (2026).

    Last reviewed July 2026 · 5 min read

  • The RMD bomb: how pre-tax savings become forced income

    SECURE 2.0 start ages 73 and 75, the Uniform Lifetime Table, a worked example of forced income growing through your 80s, and how QCDs help defuse it.

    Last reviewed July 2026 · 5 min read

  • RMD exceptions and fine print: still-working, aggregation, Roth 401(k)

    Who can delay RMDs while employed, which accounts can pool one withdrawal (IRAs and 403(b)s) and which cannot (401(k)s), the Roth 401(k) exemption since 2024, and the first-year double-RMD trap.

    Last reviewed July 2026 · 5 min read

  • The 0% capital-gains bracket is real: LTCG stacking explained

    Long-term gains stack on top of ordinary income and are taxed at 0% up to $98,900 (MFJ, 2026) — how gain harvesting steps up basis for free, and the bump-zone trap.

    Last reviewed July 2026 · 5 min read

  • NUA (net unrealized appreciation): the company-stock tax break in your 401(k) or ESOP

    Net unrealized appreciation lets employer stock leave a 401(k) or ESOP with its growth taxed at capital gains rates instead of ordinary rates — if you satisfy the strict lump-sum rules and avoid the rollover trap.

    Last reviewed July 2026 · 5 min read

  • The Social Security tax torpedo

    Provisional income, the 50% and 85% phase-in tiers, and why an IRA withdrawal in the wrong band is taxed at an effective 22.2% or 40.7% — plus how the spike ends.

    Last reviewed July 2026 · 5 min read

  • NIIT: the 3.8% surtax with the frozen threshold

    The net investment income tax explained: the lesser-of formula, why Roth conversions expose dividends to it, and how the never-indexed $250k/$200k thresholds reach further every year.

    Last reviewed July 2026 · 5 min read

  • The many MAGIs: one income, five different tests

    ACA subsidies, IRMAA, NIIT, IRA deductions, and Roth eligibility each define "modified AGI" differently — what each test adds back, the 2026 thresholds, and which ones are cliffs.

    Last reviewed July 2026 · 5 min read

  • Tax-loss harvesting without wash-sale regret

    How harvested losses actually save tax, the 61-day wash-sale window, the IRA trap that destroys a loss permanently, and why retirees in the 0% bracket should harvest gains instead.

    Last reviewed July 2026 · 5 min read

  • Safe-harbor rules: estimated taxes in retirement without penalties

    The 90%/100%/110% safe harbors, the four uneven quarterly deadlines, and the §6654(g) quirk that lets a December RMD with withholding retroactively cover the whole year.

    Last reviewed July 2026 · 5 min read

  • State taxes in retirement: the exemptions that change the map

    Pennsylvania and Illinois exempt retirement income entirely, Georgia shields $65,000 per person at 65+, nine states have no income tax — and only eight still touch Social Security.

    Last reviewed July 2026 · 5 min read

  • The widow(er)’s penalty: same money, single brackets

    Why a survivor’s taxes rise while income falls: halved deductions and brackets, halved IRMAA thresholds, lower Social Security taxability tiers — and the planning window couples have before it happens.

    Last reviewed July 2026 · 5 min read

Health & Medicare

  • The ACA subsidy cliff after 2025

    With the enhanced credits expired, subsidies end abruptly at 400% of the poverty level — how the cliff works, what counts as MAGI, and why $1 can cost thousands.

    Last reviewed July 2026 · 5 min read

  • COBRA vs. ACA: bridging health insurance before Medicare

    Two very different bridges to 65: COBRA at 102% of the full group premium versus marketplace plans with MAGI-based subsidies — costs, switching traps, and the Medicare handoff.

    Last reviewed July 2026 · 5 min read

  • Working past 65: Medicare, IRMAA, and employer coverage

    The 20-employee rule that decides whether you can delay Part B, the HSA six-month lookback trap, and why enrolling during peak earning years triggers IRMAA surcharges.

    Last reviewed July 2026 · 5 min read

  • Medicare Part B late-enrollment penalty (and Part D): calculate your lifetime surcharge

    The Part B late-enrollment penalty adds 10% per year you delay — for life — and Part D adds 1% per month. Calculate yours with 2026 premiums ($202.90 Part B, $38.99 Part D base), see the enrollment windows, and the COBRA trap that starts the meter.

    Last reviewed July 2026 · 5 min read

  • IRMAA: the Medicare surcharge with a two-year memory

    Medicare premiums are set by your income from two years earlier — the 2026 tiers, why the boundaries are cliffs, and how a Roth conversion at 63 raises premiums at 65.

    Last reviewed July 2026 · 4 min read

  • Appealing IRMAA: the SSA-44 life-changing-event form

    Medicare surcharges are priced from two-year-old income — but retiring, losing a pension, or losing a spouse lets you ask Social Security to use this year instead. What qualifies, and what never does.

    Last reviewed July 2026 · 5 min read

  • The HSA triple advantage — and its inheritance trap

    Deduction in, tax-free growth, tax-free medical withdrawals — plus the receipts strategy, Medicare premiums, and the full-taxation cliff when a non-spouse inherits.

    Last reviewed July 2026 · 5 min read

Strategy

Giving & estate

By the numbers (2026)

Using the simulator

  • How to find your maximum sustainable spending

    Using Strategy Lab Tool 1 to bisect for the highest fixed real spend that meets your success target — and Tool 1b, which solves for a spending floor instead, because under guardrails the risk moves from running out to lifestyle cuts.

    Last reviewed July 2026 · 5 min read

  • How to model a Roth conversion ladder in Deorbit Plan

    A step-by-step walkthrough of fill-the-bracket conversions: picking a bracket top and stop age, guarding the ACA and IRMAA cliffs, and reading the tax, bucket, and RMD charts that show whether the ladder pays off.

    Last reviewed July 2026 · 5 min read

  • How to compare Social Security claiming ages

    Claiming at 62 locks in 70% of your benefit; 70 locks in 124%. How to enter your FRA benefit, sweep claim ages against conversion strategies in the Strategy Lab, and read the success-vs-outcome frontier instead of a break-even rule of thumb.

    Last reviewed July 2026 · 5 min read

  • How to stress-test your plan against a 2008 crash

    Inject 2008's actual returns into every simulated path — at retirement, at a random year, or a year you fear — with or without the 2009 rebound, and read the success gauge, fan chart, and event markers to see what a worst-case sequence really costs.

    Last reviewed July 2026 · 5 min read

Educational content only — not financial, tax, or investment advice.