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Advisor Summary: Roth conversion planning software models multi-year conversion strategies across tax brackets, IRMAA thresholds, Social Security taxation, and state taxes simultaneously. The best tools show year-by-year conversion amounts, total lifetime tax savings, and client-ready comparisons between strategies. For advisors evaluating options, the critical differentiators are multi-year modeling depth, IRMAA cliff awareness, Social Security interaction, and whether the output is something you can present to a client without rebuilding it in a separate tool.

A $100,000 Roth conversion looks straightforward in a spreadsheet. Add the income, calculate the tax, done.

Now do it for 10 years. Factor in Social Security starting in year 4. Add IRMAA cliffs that trigger $3,902 in Medicare surcharges if you cross $218,000 MAGI by a single dollar. Layer in the new OBBBA senior deduction phaseout that adds 1.3 percentage points to the effective marginal rate between $150,000 and $350,000 MAGI. Account for state taxes in California at 13.3%.

That spreadsheet just broke.

This is why Roth conversion planning software exists. Not for the single-year calculation that any advisor can do with a tax table, but for the multi-year, multi-variable optimization that determines whether your client saves $47,000 or $120,000 over the course of their conversion window. The difference between those two numbers is the difference between a decent strategy and an optimal one. For our detailed comparison of six Roth conversion tools, see the companion article.

Table of Contents

What Roth Conversion Software Should Actually Do

Roth conversion planning software should model multi-year conversion strategies, based on the clients’ actual financial plan details, while accounting for the interactions between federal brackets, IRMAA thresholds, Social Security taxation, state taxes, and RMD projections. The tool should compare at least three strategies side by side and produce output clear enough for a client meeting.

Most financial planning platforms can calculate tax on a Roth conversion. That is table stakes. The hard part is optimizing the conversion amount across a 5-15 year window where every variable shifts annually.

Consider the interactions a proper tool must handle simultaneously:

Federal bracket management. A married couple with no other income can convert approximately $133,000 in the 12% bracket in 2026 (after the $32,200 standard deduction). But if Social Security starts in year 3 at $48,000, up to 85% of those benefits become taxable income, occupying bracket space and reducing the optimal conversion amount by $30,000-$40,000 per year.

IRMAA cliff modeling. Medicare surcharges are based on MAGI from two years prior (IRS/CMS). A $220,000 conversion in 2026 triggers a $3,902 annual surcharge for the couple in 2028. The software must project forward and backward simultaneously.

State tax interaction. The optimal conversion amount differs by as much as $50,000 between a client in Florida (0% state income tax) and one in California (13.3% top rate). According to the Tax Foundation, 41 states and D.C. impose some form of income tax that affects Roth conversion planning.

RMD compression. Without conversions, a $1.4M traditional IRA at age 73 generates approximately $54,000 in RMDs in the first year (IRS Uniform Lifetime Table). By age 85, the RMD percentage rises to 6.25%, potentially pushing RMDs over $80,000 even as the balance declines. Multi-year conversion modeling shows how each year’s conversion reduces the eventual RMD burden.

Advisor takeaway: If a Roth conversion tool cannot model at least 5 years forward while tracking IRMAA brackets, Social Security taxation, and RMD projections simultaneously, it is solving a simpler problem than the one your client actually has.

Six Evaluation Criteria That Matter

When evaluating Roth conversion planning software, prioritize these six capabilities: multi-year modeling, IRMAA integration, Social Security interaction, client-ready output, custodial data integration, and strategy comparison.

1. Multi-year modeling depth tied to an actual financial plan

The most important feature. Can you model a 10-year conversion strategy with different annual amounts, tied to the client’s actual financial plan? Does the tool show cumulative lifetime tax impact, not just the current-year tax bill? Does the tool know when the client plans to start Social Security? When the mortgage will be paid off? When they plan to buy a vacation home or pay for a big wedding? If not, your analysis is either hopelessly disconnected from real life or you’ve just bought yourself a lot of extra work. Some tax calculators are powerful when looking at the current year (or last year) but because they don’t connect to a real, complex long-term plan, they miss a lot of value and cost advisors a lot of extra work.

Why it matters: A single-year Roth conversion calculator tells you the tax cost of converting $100,000 this year. It does not tell you whether converting $85,000 this year and $115,000 next year (after a pension starts) produces better lifetime results. According to research from the Journal of Financial Planning, optimal Roth conversion strategies often vary conversion amounts year by year by $20,000-$40,000 based on shifting income sources.

2. IRMAA bracket integration

Does the tool know about Medicare surcharge cliffs? Does it flag when a proposed conversion crosses a threshold? Can it optimize the conversion amount to stay just below the cliff?

Why it matters: IRMAA brackets are cliffs, not graduated rates (CMS). Crossing the $218,000 MFJ threshold by $1 triggers the full $3,902 annual surcharge. Crossing $274,000 triggers $7,306. A tool that ignores IRMAA will recommend conversion amounts that cost the client thousands in Medicare premiums, eating into the very tax savings the conversion was supposed to produce.

3. Social Security taxation interaction

Does the tool model how conversion income affects the taxation of Social Security benefits? Can it show the effective marginal rate including the Social Security “tax torpedo”?

Why it matters: Social Security benefits become up to 85% taxable as income rises (IRS Publication 915). The interaction between conversion income and Social Security taxation creates effective marginal rates that can exceed the nominal bracket rate by 10-15 percentage points in certain income ranges. A couple with $48,000 in Social Security benefits faces an effective 40.7% marginal rate on income between roughly $44,000 and $66,000 due to the Social Security inclusion formula. Missing this interaction can shift the optimal conversion amount by $10,000-$20,000 per year.

4. Client-ready output

Can you present the analysis directly to a client, or do you need to rebuild it in PowerPoint? Does the tool produce clear visual comparisons between strategies?

Why it matters: The analysis is only valuable if it drives client action. According to the 2025 Kitces advisor technology survey, 68% of advisors cite “client engagement and understanding” as a top priority for planning software. A tool that produces spreadsheet exports requires hours of reformatting before a client meeting. A tool with built-in visual comparisons, timeline views, and portfolio composition charts lets you present in the same session you analyze.

5. Custodial integration

Can the tool pull current balances from Schwab, Fidelity, Pershing, or other custodians automatically?

Why it matters: Manual data entry introduces errors and adds time. An advisor running Roth scenarios for 20 clients needs current balances, cost basis, and account types flowing directly from the custodian. According to the T3 2026 technology survey, custodial data integration is the second most-requested feature among planning tools (83.3% of advisors use planning software, and integration quality is a top-three selection factor).

6. Strategy comparison

Can you run at least three strategies side by side: no conversion, fill to a specific bracket, and a custom strategy? Does the tool show cumulative tax differences over 10, 20, and 30 years?

Why it matters: The optimal Roth conversion strategy is rarely obvious. Filling the 12% bracket sounds conservative but may leave significant value on the table. Filling the 22% bracket sounds aggressive but often saves more over 20 years. Running “no conversion” vs. “fill 12%” vs. “fill 22%” vs. “fill 24%” reveals the right answer for each client, backed by specific dollar amounts the client can evaluate.

Advisor takeaway: Before demoing any Roth conversion tool, prepare a real client scenario that includes Social Security income starting mid-strategy, an IRMAA cliff that’s close to being triggered, and a 10-year window. Run this scenario in every tool you evaluate. The differences in output quality will be immediately obvious.

Why Spreadsheets Fail: A Worked Example

Manual spreadsheet analysis breaks down when variables interact across multiple years, producing results that are often counterintuitive and can cost clients tens of thousands of dollars.

Here is a scenario that illustrates why.

Meet David and Karen, ages 63 and 62.

  • $1.4M in traditional IRAs combined
  • $200,000 in a taxable brokerage account
  • $150,000 in existing Roth IRAs
  • No pension, no earned income
  • Social Security at 67: $48,000/year combined
  • Residence: Colorado (4.4% flat state income tax)
  • Both will be 65+ during 2026-2028 (OBBBA senior deduction applies)

The spreadsheet approach: An advisor opens Excel and models a flat $100,000/year conversion for 10 years. Total federal tax: approximately $143,000. The advisor presents this to the client.

What the spreadsheet missed:

  1. Social Security starting in year 4 changes everything. When Social Security starts at age 67, up to 85% of the $48,000 ($40,800) becomes taxable income. This occupies bracket space, reducing the optimal conversion amount from $100,000 to approximately $65,000-$75,000 in years 4-10. Continuing to convert $100,000 pushes the couple from the 22% bracket into the 24% bracket unnecessarily.
  2. IRMAA trigger in years 1-3. Converting $100,000 plus the standard deduction puts the couple at roughly $132,200 MAGI. Safe under the $218,000 IRMAA threshold. But the spreadsheet doesn’t flag that converting $130,000 in years 1-3 (when there’s no Social Security) fills more of the 12% bracket and is still safely below IRMAA. That extra $90,000 of conversion capacity over 3 years ($30,000 x 3) at the 12% rate instead of later at 22% saves approximately $9,000.
  3. The OBBBA senior deduction phaseout. Karen turns 65 in 2026. Both are 65+ in 2027-2028. The new senior deduction ($12,000 for a couple both 65+) phases out at 6% of MAGI above $150,000 MFJ. If MAGI is $200,000, they lose $3,000 of the deduction, adding roughly $660 in taxes ($3,000 x 22%). Over 2 years, that is $1,320 the spreadsheet did not account for. This deduction is temporary (2025-2028 only) per the One Big Beautiful Bill Act.
  4. Colorado state tax. The flat 4.4% state rate on $100,000/year is $4,400. But Colorado offers a pension/annuity exclusion of $24,000 for taxpayers 65+ that may offset some IRA income. The spreadsheet either ignores this or applies a single rate without the exclusion adjustment.

The software approach: A proper Roth conversion tool models all 10 years simultaneously, varying the conversion amount year by year based on Social Security start date, IRMAA thresholds, the senior deduction window, and state tax rules. The optimized strategy:

  • Years 1-3 (no Social Security, no full senior deduction): Convert $125,000-$130,000/year (filling the 22% bracket)
  • Year 4 (Social Security starts): Drop to $75,000
  • Years 5-10: Convert $70,000-$80,000/year (adjusted for bracket space remaining after SS)

Total federal tax under optimized strategy: approximately $128,000. That is $15,000 less than the spreadsheet’s flat $100,000/year approach. Add the avoided IRMAA surcharges and state tax optimization, and the net benefit grows to approximately $19,000.

$19,000 is the cost of not using the right tool. For an advisor managing 50 retirement clients, that scales to nearly $1 million in aggregate client value lost to suboptimal planning.

Advisor takeaway: If you’re modeling Roth conversions in a spreadsheet, you’re almost certainly leaving money on the table. The interactions between Social Security timing, IRMAA cliffs, the OBBBA senior deduction phaseout, and state taxes produce counterintuitive results that only multi-year optimization software can catch.

Comparison Table: Tools That Handle Roth Conversions

The following table compares six tools that offer Roth conversion analysis capabilities, evaluated against the six criteria above. Pricing and features are based on publicly available information as of March 2026.

Criteria Income Lab Tax Lab Holistiplan Premium RightCapital MaxiFi Covisum Tax Clarity Boldin
Multi-year modeling Yes, full multi-year optimization across strategies Yes, multi-year Roth projections (Premium tier) Yes, year-by-year tax projections within plan Yes, lifetime optimization via consumption smoothing Yes, forward-looking Roth timing optimization Yes, basic multi-year Roth Explorer
Tied to full financial plan Yes, seamless and automatic connection to cash flows and distribution down to the account level No, need to rebuilt parts of plan; Other parts of plan cannot be included Yes Yes No Yes
IRMAA integration Yes, IRMAA brackets modeled alongside tax brackets No dedicated IRMAA modeling Yes, Medicare premium modeling included Yes, IRMAA calculations included Yes, IRMAA surcharge identification (core feature) Limited IRMAA visibility
Social Security interaction Yes, SS taxation modeled within conversion strategy No SS optimization (different tool) Yes, SS analysis built into plan Yes, SS optimization included Yes, SS Timing is flagship product (separate tool) Yes, SS Explorer included
Client-ready output Yes, visual strategy comparison, timeline, portfolio shift views Yes, client-ready reports and visualizations Yes, interactive client portal with scenario editing No, PDF/Excel export only Client-ready visuals Limited client presentation
Custodial integration Schwab, Fidelity, Orion, others No custodial integration 15+ custodians, daily data sync No custodial integration No custodial integration Account aggregation available
Strategy comparison Side-by-side multi-strategy comparison Scenario analysis within tax return context Scenario comparison within plan Unlimited what-if scenarios Compares strategies by EMR bands Side-by-side scenario comparison
Best for Retirement distribution specialists who need deep Roth + SS + IRMAA integration Tax specialists who already use a separate planning platform Advisors wanting Roth within comprehensive planning Economics-focused planners who value consumption smoothing Advisors focused on marginal rate optimization Budget-conscious advisors or consumer-facing planning
Pricing ~$159/mo per advisor $150-200/mo (Premium tier, household-based) $125-150/mo per advisor $109-149/yr (consumer); PRO pricing on request Contact for pricing; associate licenses $39.99/mo $144/yr (consumer); $990/yr (advisor)

Pricing based on publicly available information as of March 2026. Contact each vendor for current pricing. All trademarks are property of their respective owners.

The Landscape: How Each Tool Approaches Roth Planning

Each of the six tools above takes a fundamentally different approach to Roth conversion analysis. Understanding that approach helps you choose the right tool for your practice.

Income Lab Tax Lab

Income Lab’s Tax Lab is purpose-built for retirement distribution optimization, with Roth conversion analysis as a core feature within its tax-aware planning engine. The tool runs multiple distribution strategies simultaneously without any additional work from the advisor, compares total lifetime taxes under each, and shows year-by-year conversion amounts alongside IRMAA brackets, Social Security taxation, and estimated federal, state, and Medicare costs. The output is client-ready: advisors can walk through the strategy comparison in a meeting without exporting to another tool. Income Lab works as a full retirement-focused planning tool on its own and also works alongside comprehensive planning platforms like RightCapital or eMoney.

Strengths: Deepest integration of Roth analysis with IRMAA, Social Security, and distribution sequencing. Rated the #1 retirement distribution tool in the T3 2026 technology survey (4.15% market share). Highest-rated Social Security analysis (8.60 rating, T3 2026). Client-ready visual output. Custodial integrations for live data. Active AI investments, including AI Plan Builder, Plan Updater, Client Interviewer, and Zoom Scribe, which help advisors build and update plans with minimal effort.

Limitations: Focused on retirement distribution, not comprehensive financial planning. Advisors need a separate planning platform for estate and insurance planning.

Holistiplan

Holistiplan approaches Roth conversions from the tax planning angle. Its Premium tier includes multi-year Roth conversion projections built on top of the tax return scanning engine. Unfortunately, because Holistiplan does not have financial planning capabilities, the multi-year engine cannot capture many of the complexities of real financial plans. And, even with this limitation, using the multi-year projections involves (imperfectly) recreating financial plan estimates, leading to duplication of efforts and lots of extra work. The tool identifies bracket breaks and visualizes where conversion income fits within federal and state tax brackets. Holistiplan is the #1 rated tax planning tool for five consecutive years in the T3 survey.

Strengths: Best-in-class tax return analysis via OCR scanning. Multi-year Roth projections show bracket impact clearly. Unlimited users per subscription. Strong advisor community.

Limitations: Not a retirement income tool. Not linked to real plans. Doesn’t cover important parts of planning, like different levels of retirement withdrawals in different years. No IRMAA modeling within the Roth analysis. No Social Security optimization. No distribution sequencing. Must be paired with a retirement planning tool. Pricing restructured in March 2025, with some users seeing significant increases (Holistiplan pricing page).

RightCapital

RightCapital handles Roth conversions within its comprehensive planning engine. Advisors can model conversions year by year as part of the broader financial plan, with tax projections and capital-gain harvesting built in. The Tax Analyzer uses OCR to scan tax returns and translate data into planning inputs. The interactive client portal lets clients explore scenarios collaboratively.

Strengths: All-in-one platform (Roth conversions, estate, accumulation, insurance in one tool). Best-in-class client portal. 15+ custodian integrations with daily data sync. Active AI investment (Smart Import, Tax Analyzer). 21.37% market share in financial planning (T3 2026). $124.95-149.95/mo per advisor (RightCapital pricing page, March 2026).

Limitations: Roth conversion analysis is part of a broader platform, not purpose-built for retirement distribution. Lacks true guardrails and dynamic spending capabilities. Tax Analyzer is less detailed than Holistiplan for dedicated tax analysis. RightCapital’s advisor base skews younger and toward smaller firms (35.75% share among 1-5 year advisors vs. 17.37% among 20+ year advisors, T3 2026).

MaxiFi

MaxiFi (formerly ESPlanner) uses an economics-based “consumption smoothing” methodology developed by Boston University economist Laurence Kotlikoff. The Roth Conversion Optimizer (Premium tier) automates strategy optimization by calculating the conversion amounts that maximize the household’s sustainable living standard. Tax modeling is highly detailed, including federal, state, FICA, and IRMAA.

Strengths: Academically rigorous methodology. Extremely detailed tax modeling at a fraction of enterprise pricing ($109-149/yr for consumers). Automated Roth conversion optimization, not just analysis. Updated with OBBBA 2025 tax changes.

Limitations: Consumer-first product. No interactive client portal (PDF/Excel export only). No custodial integrations. Minimal market presence among professional advisors. Small team with limited support capacity. The economics-based approach requires advisors to learn a different conceptual framework.

Covisum Tax Clarity

Covisum’s Tax Clarity tool focuses specifically on effective marginal tax rate analysis and Roth conversion timing optimization. Founded by practicing financial advisor Joe Elsasser, CFP, the tool calculates effective marginal rates including hidden interactions (IRMAA surcharges, Social Security taxation thresholds) and optimizes conversion amounts to stay within specific rate bands. The companion Social Security Timing tool is among the leading SS optimization tools in the market.

Strengths: Effective marginal rate analysis is the core differentiator. Purpose-built for identifying hidden tax cliffs and IRMAA surcharges. Practitioner-built by a CFP. No-contract, cancel-anytime pricing. 10-day free trial.

Limitations: Each Covisum tool is separate (Tax Clarity, Social Security Timing, SmartRisk, Income InSight). No unified retirement income plan that ties everything together. No custodial integrations. No interactive client portal. Small company (approximately 10 employees). Limited integration ecosystem.

Boldin (formerly NewRetirement)

Boldin offers a Roth Conversion Explorer within its PlannerPlus tier. The tool lets users model conversions alongside a broader retirement plan with 250+ inputs. Boldin recently added a Spending Guardrails Insight feature and offers side-by-side scenario comparisons. The platform has a large consumer user base with an advisor-facing PlannerPro tier.

Strengths: Affordable ($144/yr consumer, $990/yr advisor). Broad planning with 250+ inputs. Roth Conversion Explorer for modeling strategies. Recently added guardrails feature. Weekly live classes on tax planning and Roth strategies.

Limitations: Consumer-first design. Not built for professional advisor workflow. Guardrails feature is newly launched and less sophisticated than established implementations (focuses on probability of success – a flawed concept, especially for guardrails). No CRM or custodian integrations. No meaningful presence in professional advisor technology surveys (T3, Kitces). May be perceived as “not professional-grade” by established advisory firms.

Two Client Scenarios: Choosing the Right Tool

Scenario 1: The dedicated retirement income practice

Profile: Sarah runs a fee-only RIA focused on clients within 5 years of retirement or recently retired. Her typical client has $800K-$2M in traditional IRAs, is navigating Social Security timing, and needs a multi-year Roth conversion strategy alongside withdrawal planning. She uses eMoney for comprehensive planning and needs a specialized tool for the retirement income piece.

What Sarah needs: Deep Roth conversion modeling that integrates with Social Security timing and IRMAA management. Client-ready output she can present without reformatting. A tool that works alongside eMoney, not one that replaces it.

Best fit: Income Lab Tax Lab or Covisum Tax Clarity + Social Security Timing. Income Lab provides the deepest integration of Roth analysis with distribution sequencing in a single tool. Covisum provides focused tax clarity with marginal rate analysis, but Sarah would need the separate Social Security Timing tool and would assemble the pieces herself. For Sarah’s practice, where retirement income is the core service, Income Lab’s integrated approach saves time and produces a more cohesive client presentation. Income Lab also gives Sarah access to best-in-industry retirement guardrail capabilities, something that sets her apart with her target clientele.

Scenario 2: The comprehensive planner who does everything

Profile: Marcus serves clients from age 30 through retirement. He does accumulation planning, college planning, estate work, insurance, and retirement income. Roth conversions come up for his older clients, but they represent about 30% of his practice. He wants one platform that handles everything, even if no single feature is the deepest available.

What Marcus needs: Roth conversion analysis that’s good enough to serve his retirement clients within the same platform he uses for everything else. He doesn’t want to pay for and learn a separate tool just for Roth conversions.

Best fit: RightCapital. The platform handles Roth conversion analysis within the same tool Marcus uses for his 35-year-old accumulation clients and his 70-year-old distribution clients. The client portal lets all clients see their plans interactively. Roth modeling won’t be as deep as a specialized tool, but it may be sufficient for a practice where retirement income is one of many services. If Marcus finds that his retirement clients need deeper analysis, he can add Income Lab alongside his primary platform without abandoning it.

Advisor takeaway: The right Roth conversion tool depends on the shape of your practice. If retirement income is your core service, invest in specialized depth. If it’s one piece of a comprehensive offering, choose the platform that handles the most use cases well enough. The worst option is a spreadsheet for either advisor.

What to Ask in a Demo

When evaluating Roth conversion planning software, bring a specific client scenario and ask these questions:

  1. “Show me a 10-year conversion strategy with Social Security starting in year 4.” This tests multi-year modeling depth and Social Security interaction. If the tool can only model one year at a time, it fails this test.
  2. “My client is at $215,000 MAGI. What happens if I convert $5,000 more?” This tests IRMAA cliff awareness. The right tool should flag that $218,000 is a cliff and show the $3,902 surcharge cost of crossing it.
  3. “Compare no conversions vs. filling the 12% bracket vs. filling the 22% bracket over the full window.” This tests strategy comparison. You should see three strategies side by side with cumulative tax differences at 10, 20, and 30 years.
  4. “My client is 66 and in California. How does the state tax change the optimal conversion?” This tests state tax integration. California’s 13.3% top rate dramatically changes the math.
  5. “Show me what you would present to the client.” This tests client-ready output. If the answer involves exporting to Excel and rebuilding in PowerPoint, the tool fails the presentation test.
  6. “How does the new OBBBA senior deduction phaseout affect the conversion amount?” This tests whether the tool has been updated for current tax law. The senior deduction ($6,000 per qualifying person, phasing out at 6% of MAGI above $150,000 MFJ) is new for 2025-2028 per the One Big Beautiful Bill Act. Many tools have not yet integrated it.

Income Lab’s Tax Lab automates multi-year Roth conversion analysis with IRMAA bracket management, Social Security interaction, and side-by-side strategy comparison. Book a 30-minute demo to see it with your client scenarios.

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Sources

Last verified: March 2026

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VISUAL PLAN (for WordPress deployment):

  1. After comparison table: Annotated screenshot of Income Lab Tax Center showing multi-strategy comparison (request from Eric/product team)
  2. After worked example: Simple chart showing flat $100K/yr vs. optimized strategy tax totals
  3. After evaluation criteria section: Infographic of the 6 criteria with icons
  4. Embedded video: Tax-Smart Distribution Planning (YouTube ID: iaqrbuNdkLY) near the comparison section
  5. After “what to ask” section: Screenshot of Tax Lab side-by-side view answering one of the demo questions

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Best Roth Conversion Software for Financial Advisors (2026) → Retirement Cash Flow Planning: A Step-by-Step Guide for Advisors → Income Lab vs. eMoney Advisor: An Honest Comparison for Financial Advisors → Retirement Paycheck: What It Is and How Advisors Build One →

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