Best Tax Planning Software of 2026
We tested 8 platforms built for complex HNW tax situations — Roth conversion modeling, IRMAA avoidance, RMD sequencing, and capital gains harvesting.
Quick Comparison
| # | Lender | Rating | Best Rate | Best For | |
|---|---|---|---|---|---|
RightCapitalEditor's Choice | 4.8 | 50+ tax strategies modeled | HNW Planning | Get Demo | |
| 2 | 4.7 | AI-powered return parsing | Tax Return Analysis | Get Demo | |
| 3 | BoldinDIY Friendly | 4.6 | $120/yr PlannerPlus | DIY Retirees | Try Free |
| 4 | 4.4 | Full Integration custodian sync | Enterprise RIAs | Get Demo | |
| 5 | 4.2 | $14.99/mo starting price | Tax-Aware Tracking | Try Monarch |
Best Tax Planning Software 2026: Quick Comparison
| Software | Target User | Roth Conversion Modeling | Starting Price | Best For |
|---|---|---|---|---|
| RightCapital | RIAs & advisors | Yes — 30+ year projections | Per-advisor seat | Comprehensive HNW Planning |
| Holistiplan | Financial advisors | Yes — return-based | Per-advisor seat | Tax Return Analysis |
| Boldin (NewRetirement) | Self-directed | Yes | $120/yr PlannerPlus | DIY Retirement Tax Planning |
| eMoney Advisor | RIAs & broker-dealers | Integrated | Enterprise pricing | Enterprise Wealth Management |
| Monarch Money Pro | Self-directed HNW | Basic | $14.99/mo | Tax-Aware Budgeting |
Pricing and features current as of June 2026. Advisor platforms require a licensed professional relationship.
RightCapital
Comprehensive financial planning platform with deep tax scenario modeling
RightCapital is what financial advisors use when the tax situation is genuinely complex: Roth conversion ladders timed to avoid IRMAA surcharges, coordinating Social Security with RMDs, modeling qualified opportunity zones. If you have a fee-only advisor, ask whether they use RightCapital — it signals a planning-first practice.
- Models 50+ tax strategies including Roth conversions, IRMAA avoidance, and Social Security optimization
- 30-year tax projections identify the optimal conversion window before RMDs begin
- Monte Carlo simulation overlays market risk onto tax scenarios
- Advisor-facing software — clients need an RIA relationship to access it
- Learning curve is steep for advisors new to tax planning integration
- Pricing is per-advisor seat, not per-client — cost adds up for solo practitioners
Holistiplan
AI-powered tax return analysis that surfaces planning opportunities instantly
Holistiplan solves a specific problem: most advisors are not CPAs and don't naturally read tax returns for planning opportunities. The AI parsing engine turns a 1040 into an actionable planning summary in under 60 seconds. It's the fastest way to find Roth conversion room, IRMAA exposure, and capital gain harvesting opportunities hiding in a client's return.
- Uploads a client's tax return and extracts all relevant data in seconds via AI parsing
- Automatically surfaces Roth conversion opportunities, unused deductions, and bracket room
- Generates clean client-facing reports that explain findings without jargon
- Focused on current-year analysis — less powerful for 10-year forward projections than RightCapital
- Advisor-only access — no consumer version available
- Requires a tax return upload, which some clients are reluctant to provide
Boldin (NewRetirement)
Self-directed retirement tax planning with Roth modeling and Social Security optimization
Boldin is the best self-directed option for HNW individuals who want to model their own retirement tax strategy without relying on an advisor for every scenario. The Social Security optimizer and Roth conversion modeler handle 80% of what most pre-retirees actually need at $120/year.
- Consumer-accessible at $120/year — no advisor relationship required
- Social Security optimization models claiming age scenarios against tax and longevity outcomes
- Roth conversion modeling lets self-directed investors run scenarios without hiring an advisor
- Less powerful than advisor platforms for complex situations — no DFA fund access or multi-entity modeling
- Interface is functional but less polished than consumer fintech alternatives
- Accuracy depends heavily on the quality of data the user inputs
eMoney Advisor
Enterprise-grade wealth management platform used by the largest RIA firms
eMoney Advisor is the platform that large RIA firms use to manage the full client relationship — not just tax planning. If your advisor uses eMoney, you get a consolidated view of your entire financial picture. The tax planning module is solid but not the reason advisors choose eMoney.
- Deep integration with custodians (Fidelity, Schwab, TD) for real-time account data
- Client portal gives HNW households a single view of all accounts, assets, and projections
- Owned by Fidelity, ensuring enterprise-grade security and uptime
- Tax planning features are present but less specialized than RightCapital or Holistiplan
- Enterprise pricing puts it out of reach for solo advisors and boutique RIAs
- Client-facing UI improvements lag behind consumer-grade fintech
Monarch Money Pro
Tax-aware budgeting and net worth tracking for self-directed HNW households
Monarch Money Pro earns its place as a budgeting and tracking layer, not a tax planning platform. If you want to understand your tax exposure from realized capital gains and track net worth in real time, it delivers. For actual tax scenario modeling, pair it with Boldin or engage a RightCapital-using advisor.
- Best-in-class transaction categorization with capital gains tracking across taxable accounts
- Net worth dashboard tracks all assets in real time
- At $14.99/month, the lowest price point on this list
- Tax projection is basic — no Roth conversion modeling, no IRMAA simulation
- Not a replacement for dedicated tax planning software; more of a complement
- No advisor integration — self-directed only
Methodology
How We Evaluate Tax Planning SoftwareOur editorial team evaluates tax planning platforms across five weighted categories: depth of Roth conversion and RMD modeling (30%), IRMAA and Social Security integration (25%), quality of forward tax projections (20%), accessibility for self-directed vs. advisor-dependent users (15%), and interface usability (10%).
We focus exclusively on platforms designed for complex HNW tax situations, not general tax filing software. Platforms are evaluated based on published documentation, demo walkthroughs, and user feedback from fee-only financial advisors. We update rankings semi-annually.
CalcMoney may receive compensation from partners when you click affiliate links. This does not influence our rankings or editorial content. Our recommendations are based on independent research. Results are estimates for informational purposes only. Consult a licensed financial professional before making tax or financial planning decisions.
Frequently Asked Questions
Tax Planning Software FAQ
Tax planning software models future scenarios before year-end: how much to convert to a Roth IRA, when to realize capital gains, how to sequence withdrawals to minimize lifetime tax. Tax filing software (TurboTax, H&R Block) prepares your return after the fact — it reports what happened, not what should happen.
The two are complements, not substitutes. Planning software is where wealth is preserved; filing software is where it's recorded.
IRMAA (Income-Related Monthly Adjustment Amount) is a Medicare surcharge triggered when your modified adjusted gross income exceeds certain thresholds. In 2026, single filers crossing $103,000 pay an additional $69.
90/month on Medicare Part B. At $129,000, that surcharge jumps to $174.
70/month. Roth conversions increase MAGI and can tip you into a higher IRMAA tier — adding $800–$6,000 per year in Medicare premiums.
Tax planning software models the net effect of a conversion against the IRMAA cost.
A Roth conversion ladder converts traditional IRA funds to Roth over multiple years, typically during the gap between retirement and RMD age (72 under current law). The goal is to fill your current tax bracket each year — converting enough to pay tax at 22% or 24% now rather than potentially 32%+ when Social Security, RMDs, and other income stack.
The strategy works best for individuals who retire before 65 and have 5–10 years of low-income runway before RMDs force taxable distributions.
Tax-loss harvesting sells investments at a loss to offset realized capital gains — reducing your taxable income by the loss amount. Capital losses first offset capital gains dollar-for-dollar, then offset up to $3,000 of ordinary income per year, with any remainder carried forward to future years.
At a $500K taxable account, a 10% correction can yield $30,000–$50,000 in harvestable losses. Robo-advisors like Betterment and Wealthfront automate this daily.
Manual harvesting at year-end can still capture meaningful savings, particularly after high-volatility years.
The crossover point is typically $500,000+ in annual income, where bracket management, IRMAA avoidance, estate planning, and qualified opportunity zones create savings that exceed advisory fees. Below that threshold, a CPA who proactively plans (rather than just files) often provides adequate coverage.
Above $1M, the complexity of capital gains timing, charitable structures, business entity optimization, and estate tax triggers typically warrants dedicated planning software and a coordinated team of CPA, attorney, and financial advisor.