Tax Loss Harvesting Blog

Guides, strategies, and insights for tax-efficient investing.

Start with the tax loss harvesting rules for 2026, then see savings by portfolio size. Understand choosing the right tax lot and multi-account tax loss harvesting — one missed cross-account wash sale cost $1,904. High earners should read about the 3.8% NIIT and your harvested losses. Crypto investors: crypto and the wash sale rule still don’t mix — legally. And see how software picks the right lot across all your accounts simultaneously.

Open Tax Lot Tracking Across Brokerages
July 30, 2026 · 9 min read

Open Tax Lot Tracking Across Brokerages

Open tax lot tracking shows every unsold taxable lot across brokerages so investors can find losses, avoid wash sales, and choose better sales before trading.

Coordinating Multiple Taxable Accounts Before a Harvest
July 29, 2026 · 9 min read

Coordinating Multiple Taxable Accounts Before a Harvest

A pre-trade checklist for coordinating losses, gains, lots, and wash-sale timing across multiple taxable accounts.

E*TRADE Tax Loss Harvesting Software Checklist
July 28, 2026 · 9 min read

E*TRADE Tax Loss Harvesting Software Checklist

An E*TRADE tax loss harvesting software checklist for comparing lot access, wash sale coverage, Core Portfolios limits, and existing-account overlays.

Tax-Loss Harvesting Software for Interactive Brokers Investors
July 27, 2026 · 9 min read

Tax-Loss Harvesting Software for Interactive Brokers Investors

Tax loss harvesting software Interactive Brokers investors use should read open lots, gains, wash sale timing, and outside accounts without moving assets.

Tax-Loss Harvesting Software for Robinhood Investors
July 26, 2026 · 9 min read

Tax-Loss Harvesting Software for Robinhood Investors

Tax loss harvesting software Robinhood investors can use should scan tax lots, gains, and wash sale risk without moving assets or missing outside buys.

Tax-Loss Harvesting Software for Schwab Investors
July 25, 2026 · 9 min read

Tax-Loss Harvesting Software for Schwab Investors

Tax loss harvesting software Schwab investors can use should scan lots, wash sale risk, and gains across accounts without moving assets or missing outside buys.

Tax-Loss Harvesting Software for Fidelity Investors
July 24, 2026 · 9 min read

Tax-Loss Harvesting Software for Fidelity Investors

Tax loss harvesting software Fidelity investors can use should scan lots, wash sale risk, and gains across accounts without moving existing Fidelity assets.

Multi-Brokerage Tax Loss Harvesting Software
July 23, 2026 · 9 min read

Multi-Brokerage Tax Loss Harvesting Software

Multi-brokerage tax loss harvesting software coordinates lots, gains, and wash sale risk across existing accounts so households can harvest without moving assets.

Tax-Loss Harvesting Across Brokerage Accounts: Household Guide
July 22, 2026 · 9 min read

Tax-Loss Harvesting Across Brokerage Accounts: Household Guide

A household guide to coordinating tax lots, gains, and wash-sale risk across brokerage accounts without moving portfolio assets.

Tax Loss Harvesting Without Direct Indexing
July 21, 2026 · 9 min read

Tax Loss Harvesting Without Direct Indexing

Tax loss harvesting without direct indexing uses existing brokerage lots to find losses, avoid wash sales, and offset gains without a new managed portfolio.

Direct Indexing Alternative Tax Loss Harvesting
July 20, 2026 · 9 min read

Direct Indexing Alternative Tax Loss Harvesting

Direct indexing alternative tax loss harvesting lets investors find tax losses in existing brokerage portfolios without buying a managed index product.

Tax Loss Harvesting Without Robo Advisor Accounts
July 19, 2026 · 10 min read

Tax Loss Harvesting Without Robo Advisor Accounts

Tax loss harvesting without robo advisor help lets investors keep existing brokerage accounts while adding lot-level loss detection and wash sale checks.

Tax Loss Harvesting Software vs Robo Advisor Portfolios
July 15, 2026 · 10 min read

Tax Loss Harvesting Software vs Robo Advisor Portfolios

Tax loss harvesting software vs robo advisor portfolios comes down to control, custody, lot visibility, outside-account wash sale risk, and tax decisions.

Tax Loss Harvesting Alerts: What Investors Should See
July 12, 2026 · 9 min read

Tax Loss Harvesting Alerts: What Investors Should See

Tax loss harvesting alerts should show loss size, tax value, wash sale risk, replacement timing, and gain offsets before an investor decides which lot to sell.

Tax Loss Harvesting Software for Existing Brokerage Accounts
July 11, 2026 · 10 min read

Tax Loss Harvesting Software for Existing Brokerage Accounts

Tax loss harvesting software for existing brokerage accounts adds lot-level loss scans, wash sale checks, and tax-aware sell decisions without moving assets.

Tax Loss Harvesting Calculator: What It Can and Cannot Tell You
July 10, 2026 · 9 min read

Tax Loss Harvesting Calculator: What It Can and Cannot Tell You

A tax loss harvesting calculator estimates potential tax savings, but real portfolios need lot data, gain offsets, and wash sale checks before selling.

Tax Lot Optimization Tools: Software Evaluation Checklist
July 9, 2026 · 10 min read

Tax Lot Optimization Tools: Software Evaluation Checklist

Use this tax lot optimization tools checklist to compare whether software can evaluate lots, gains, wash sales, brackets, and matched-pair opportunities before a sale.

Wash Sale Rebuy Notifications for Tax Loss Harvesting
July 8, 2026 · 11 min read

Wash Sale Rebuy Notifications for Tax Loss Harvesting

Wash sale rebuy notifications tell investors what not to buy, in which accounts, and when the window clears after a tax loss harvesting sale across a household.

Tax Loss Harvesting Algorithm: How Sell Signals Work
July 7, 2026 · 11 min read

Tax Loss Harvesting Algorithm: How Sell Signals Work

A tax loss harvesting algorithm compares lots, gains, wash sale risk, and basis-raising value to decide whether an investor should sell, wait, or pair trades today.

Automated Tax Loss Harvesting Without Moving Accounts
June 30, 2026 · 11 min read

Automated Tax Loss Harvesting Without Moving Accounts

Automated tax loss harvesting scans existing brokerage accounts for lot-level losses, wash sale risk, sell signals, and basis-raising opportunities without moving the portfolio.

Tax-Loss Harvesting Annual Savings Estimate: Calculate Yours
June 28, 2026 · 10 min read

Tax-Loss Harvesting Annual Savings Estimate: Calculate Yours

A tax-loss harvesting annual savings estimate shows expected tax savings from harvestable losses, tax rates, wash sale risk, and software lot checks all year.

Tax Loss Harvesting Software: How It Works and Saves Money
June 26, 2026 · 11 min read

Tax Loss Harvesting Software: How It Works and Saves Money

Tax loss harvesting software finds portfolio losses, offsets taxable gains, avoids wash sales, and helps investors keep more after tax.

Tax Loss Harvesting Software for Your Existing Portfolio
June 24, 2026 · 10 min read

Tax Loss Harvesting Software for Your Existing Portfolio

Tax loss harvesting software for an existing portfolio lets investors keep their brokerage accounts while adding lot-level tax intelligence.

Tax-Loss Harvesting on E*TRADE Without Moving Assets
June 10, 2026 · 13 min read

Tax-Loss Harvesting on E*TRADE Without Moving Assets

Tax loss harvesting on E*TRADE is possible but requires manual lot selection, has no cross-account wash sale tracking, and misses lot-level losses inside winning positions.

Buy-and-Hold Portfolios and Embedded Capital Gains
June 8, 2026 · 6 min read

Buy-and-Hold Portfolios and Embedded Capital Gains

How to measure embedded capital gains in a long-held portfolio and plan future sales without treating every unrealized gain as an immediate bill.

Continuous vs. Annual Tax-Loss Harvesting
June 8, 2026 · 6 min read

Continuous vs. Annual Tax-Loss Harvesting

What more frequent tax-lot monitoring can capture, what it costs, and why no fixed multiple of losses or savings is guaranteed.

Mid-Year Tax Planning 2026: Finding Losses Near Market Highs
June 4, 2026 · 11 min read

Mid-Year Tax Planning 2026: Finding Losses Near Market Highs

A mid-year 2026 checklist for finding lot-level losses, reviewing realized gains, and planning around current tax brackets.

California Concentrated Stock: A Tax-Aware Diversification Plan
June 2, 2026 · 7 min read

California Concentrated Stock: A Tax-Aware Diversification Plan

How California investors can use tax lots, staged sales, harvested losses, and charitable planning to diversify concentrated stock.

How to Raise Cost Basis With the 0% Capital-Gains Bracket
May 29, 2026 · 6 min read

How to Raise Cost Basis With the 0% Capital-Gains Bracket

A practical gain-harvesting framework for raising basis inside the 0% federal long-term capital-gains band.

Retiree Case Study: Realizing Gains in the 0% Bracket
May 27, 2026 · 6 min read

Retiree Case Study: Realizing Gains in the 0% Bracket

A 2026 example showing how ordinary income and qualified dividends determine how much long-term gain can fit in the 0% federal band.

RSU Wash-Sale Case Study: Cross-Account Replacement Shares
May 18, 2026 · 6 min read

RSU Wash-Sale Case Study: Cross-Account Replacement Shares

How an RSU vest and an IRA purchase can partially disallow an employer-stock loss, with share matching and basis treatment.

State Capital Gains Tax Rates in 2026
May 18, 2026 · 7 min read

State Capital Gains Tax Rates in 2026

How selected states treat capital gains in 2026 and why residency, loss rules, surtaxes, and local tax matter more than one top-rate table.

Matched-Pair Tax-Loss Harvesting: Gains and Losses Together
May 9, 2026 · 6 min read

Matched-Pair Tax-Loss Harvesting: Gains and Losses Together

How pairing a realized gain with a realized loss can raise basis in one holding—and why the result is deferral, not free money.

Crypto Wash Sale Rule 2026: Does It Apply to Bitcoin?
May 5, 2026 · 12 min read

Crypto Wash Sale Rule 2026: Does It Apply to Bitcoin?

As of July 2026, direct crypto is still treated as property for federal tax purposes, so the stock wash sale rule does not apply. Bitcoin ETFs are different.

Tax-Loss Harvesting vs. a 401(k): Different Tax Jobs
April 30, 2026 · 5 min read

Tax-Loss Harvesting vs. a 401(k): Different Tax Jobs

Why 401(k) contributions and tax-loss harvesting are not substitutes, plus a practical order for using both in 2026.

Tax-Loss Harvesting for Retirees and the 0% Bracket
April 29, 2026 · 6 min read

Tax-Loss Harvesting for Retirees and the 0% Bracket

How retirees can coordinate taxable income, the 0% capital-gains band, carryforwards, RMDs, and portfolio sales in 2026.

How Tax Lots Reveal Losses Inside Winning Positions
April 28, 2026 · 6 min read

How Tax Lots Reveal Losses Inside Winning Positions

Why a position with an overall gain can still contain individual loss lots, plus the checks to run before harvesting one.

NVDA Tax-Lot Case Study: FIFO vs. HIFO
April 24, 2026 · 8 min read

NVDA Tax-Lot Case Study: FIFO vs. HIFO

A four-lot NVIDIA example showing how FIFO, HIFO, holding period, and portfolio losses can change the tax cost of raising cash.

Optimal Tax Lot Selection: When HIFO Is Not Enough
April 22, 2026 · 10 min read

Optimal Tax Lot Selection: When HIFO Is Not Enough

Optimal tax lot selection ranks basis, holding period, tax brackets, gains, losses, and wash sale risk so investors do not stop at HIFO.

Tax-Loss Harvesting for Business Owners
April 22, 2026 · 6 min read

Tax-Loss Harvesting for Business Owners

How variable income, a business sale, estimated taxes, and taxable investment gains can change a business owner's harvesting plan.

Capital Gains Tax Rates 2026: 0%, 15%, 20%, and NIIT
April 20, 2026 · 10 min read

Capital Gains Tax Rates 2026: 0%, 15%, 20%, and NIIT

The 2026 federal long-term capital-gains thresholds, how gains stack above ordinary income, and when the 0% band may apply.

Net Investment Income Tax in 2026: Thresholds and Losses
April 17, 2026 · 6 min read

Net Investment Income Tax in 2026: Thresholds and Losses

How the 3.8% net investment income tax works in 2026 and how capital losses can reduce—but not multiply—the NIIT effect.

FIFO vs Specific ID: The Tax Lot Choice Worth $2,430 on One Sale
April 16, 2026 · 10 min read

FIFO vs Specific ID: The Tax Lot Choice Worth $2,430 on One Sale

FIFO vs specific identification, with the math: picking the right tax lot saved $2,430 on a single $60,000 sale. How to set it up at your brokerage today.

How Much Can Tax-Loss Harvesting Save?
April 10, 2026 · 6 min read

How Much Can Tax-Loss Harvesting Save?

A transparent way to estimate current tax deferral from harvested losses without using portfolio size as a savings guarantee.

What Is Tax Lot Optimization? The Start-Here Guide
April 10, 2026 · 8 min read

What Is Tax Lot Optimization? The Start-Here Guide

Tax lot optimization means choosing which shares to sell before a taxable trade. Start here, then compare FIFO, optimal lot selection, and software tools.

Tax-Loss Harvesting Rules 2026
April 1, 2026 · 10 min read

Tax-Loss Harvesting Rules 2026

The 2026 tax loss harvesting rules in one place: wash sales, the $3,000 limit, carryovers, and the deadline, applied across all your brokerage accounts.

What Is Tax Loss Harvesting? The Complete Guide
March 30, 2026 · 8 min read

What Is Tax Loss Harvesting? The Complete Guide

A complete guide to tax-loss harvesting: tax lots, gain offsets, wash-sale rules, replacement exposure, and long-term tax deferral.

Tax-Loss Harvesting for High-Income Investors
March 29, 2026 · 6 min read

Tax-Loss Harvesting for High-Income Investors

How high-income investors can value harvested losses across capital-gains rates, NIIT, state tax, and multi-year carryforwards.

How Tax-Lot Selection Changes Capital-Gains Tax
March 25, 2026 · 6 min read

How Tax-Lot Selection Changes Capital-Gains Tax

A worked explanation of how FIFO, highest-cost, and specific-lot choices can produce very different capital-gains tax outcomes.

Direct Indexing vs. ETF Tax-Loss Harvesting
March 18, 2026 · 6 min read

Direct Indexing vs. ETF Tax-Loss Harvesting

How direct indexing and ETF harvesting differ in opportunity set, complexity, cost, tracking error, and after-tax measurement.

What Your Brokerage App Doesn't Show About Tax Lots
February 23, 2026 · 5 min read

What Your Brokerage App Doesn't Show About Tax Lots

What position-level brokerage charts omit about tax lots, after-tax return, embedded gains, and household wash-sale risk.

Why Smart Investors Still Trigger Wash Sales After Harvesting
February 8, 2026 · 3 min read

Why Smart Investors Still Trigger Wash Sales After Harvesting

Why recurring buys, dividend reinvestment, spouse accounts, and delayed records cause wash sales even for experienced investors.

Why Smart Investors Still Trigger Wash Sales
February 8, 2026 · 3 min read

Why Smart Investors Still Trigger Wash Sales

A practical look at why the wash-sale rule becomes difficult across real accounts, recurring purchases, and replacement trades.

What Tax-Loss Harvesting Changes—and What It Doesn’t
January 18, 2026 · 6 min read

What Tax-Loss Harvesting Changes—and What It Doesn’t

A clear boundary between the tax-lot effects of harvesting and the investment outcomes it cannot promise.

How Tax Efficiency Becomes Your Greatest Source of Alpha
January 13, 2026 · 4 min read

How Tax Efficiency Becomes Your Greatest Source of Alpha

Why after-tax return can differ even when market return is identical, and how repeatable tax decisions can create tax alpha.

How Tax Deferral Can Support Long-Term Compounding
January 5, 2026 · 6 min read

How Tax Deferral Can Support Long-Term Compounding

How tax deferral can leave more capital invested—and why future tax, fees, and replacement basis belong in the calculation.

The Tax Tradeoffs Inside a Buy-and-Hold Portfolio
January 2, 2026 · 6 min read

The Tax Tradeoffs Inside a Buy-and-Hold Portfolio

How a buy-and-hold portfolio can accumulate embedded gains, temporary loss lots, and difficult liquidity decisions.

What Your Brokerage Performance Chart Leaves Out
December 24, 2025 · 5 min read

What Your Brokerage Performance Chart Leaves Out

Why a brokerage return chart cannot show embedded taxes, lot-selection choices, or the after-tax amount available to spend.

How to Compare Two Portfolios After Tax
December 15, 2025 · 6 min read

How to Compare Two Portfolios After Tax

A measurement framework for comparing after-tax wealth when pre-tax returns look identical.

Why Waiting for Major Crashes Misses Harvesting Opportunities
December 9, 2025 · 6 min read

Why Waiting for Major Crashes Misses Harvesting Opportunities

Why crisis-only harvesting can miss temporary loss lots—and why more frequent monitoring still needs trade-level guardrails.

Regular Tax-Loss Harvesting vs. Market Timing Over 20 Years
November 29, 2025 · 6 min read

Regular Tax-Loss Harvesting vs. Market Timing Over 20 Years

Why staying invested and managing taxes is different from predicting markets—and how to compare the two without inventing a backtest.

How Down Markets Create Long-Term Tax Opportunities
November 23, 2025 · 5 min read

How Down Markets Create Long-Term Tax Opportunities

How down markets can create long-term tax assets through disciplined harvesting, reinvestment, and gain-offset planning.

Raising Cost Basis Through Tax Pairing
November 11, 2025 · 5 min read

Raising Cost Basis Through Tax Pairing

A worked example of pairing harvested losses with gains to raise cost basis while controlling the current-year tax result.

Raising Cost Basis With Tax-Aware Gain Realization
November 4, 2025 · 5 min read

Raising Cost Basis With Tax-Aware Gain Realization

Why investors sometimes realize gains alongside losses to increase cost basis, reduce future embedded gains, and improve flexibility.

Using Short-Term Losses to Offset Gains and Raise Cost Basis
October 9, 2025 · 5 min read

Using Short-Term Losses to Offset Gains and Raise Cost Basis

How short-term losses enter the capital-gain netting process and can support a deliberate gain-realization and cost-basis plan.

How to Stay Invested After Harvesting a Loss
September 16, 2025 · 5 min read

How to Stay Invested After Harvesting a Loss

A practical replacement-security workflow for maintaining portfolio exposure after a tax-loss sale without ignoring wash-sale risk.

Tax-Loss Harvesting With Dividends and Carryforwards
September 9, 2025 · 7 min read

Tax-Loss Harvesting With Dividends and Carryforwards

A complete framework for coordinating dividends, capital gains, carryforward losses, 0% rate room, and wash-sale controls.

Tax-Loss Harvesting as a Couple in 2026
September 1, 2025 · 6 min read

Tax-Loss Harvesting as a Couple in 2026

How couples can coordinate taxable accounts, gains, losses, dividends, and 2026 brackets when planning household tax-loss harvesting.

Carryforward Losses, Capital Gains, and Dividend Planning
August 26, 2025 · 5 min read

Carryforward Losses, Capital Gains, and Dividend Planning

How carryforward losses can offset capital gains in a dividend portfolio—and the limits investors need to understand.

Harvesting Before Dividend Dates Without Creating Taxable Income
August 20, 2025 · 5 min read

Harvesting Before Dividend Dates Without Creating Taxable Income

When harvesting before a dividend date can reduce unwanted taxable income—and when selling too early creates a worse result.

Harvesting Around Dividend Dates: How to Boost After-Tax Returns
August 12, 2025 · 5 min read

Harvesting Around Dividend Dates: How to Boost After-Tax Returns

How dividend dates, price changes, holding periods, and tax lots can affect the timing and value of a tax-loss harvest.

Tax-Loss Harvesting in a Bull Market
July 30, 2025 · 5 min read

Tax-Loss Harvesting in a Bull Market

Why rising markets can still contain losing tax lots—and how to evaluate them without forcing unnecessary trades.

Using Leverage With Tax-Loss Harvesting: Risks and Tradeoffs
July 21, 2025 · 6 min read

Using Leverage With Tax-Loss Harvesting: Risks and Tradeoffs

Why tax-loss harvesting does not make leverage safer, plus the tax, interest, margin-call, and portfolio risks to model first.

When Tax Loss Harvesting Is Not Worth It
July 17, 2025 · 6 min read

When Tax Loss Harvesting Is Not Worth It

Tax loss harvesting is not worth it when tax value is small, wash-sale risk is high, replacement exposure is poor, or losses cannot be used soon.

Tax Alpha: Measuring After-Tax Portfolio Improvement
July 8, 2025 · 5 min read

Tax Alpha: Measuring After-Tax Portfolio Improvement

What tax alpha means, how tax deferral differs from permanent savings, and which assumptions belong in an after-tax comparison.

Tax-Loss Harvesting During International Market Dips
July 1, 2025 · 6 min read

Tax-Loss Harvesting During International Market Dips

How to evaluate loss lots in international funds while preserving intended regional, currency, and factor exposure.

Bitcoin Tax-Loss Harvesting: Basis, Trades, and Records
July 1, 2025 · 6 min read

Bitcoin Tax-Loss Harvesting: Basis, Trades, and Records

How a Bitcoin sale creates a reportable capital gain or loss, which records matter, and why transaction costs and changing rules need attention.

Using Software to Monitor Wash Sales Across Brokerages
June 24, 2025 · 5 min read

Using Software to Monitor Wash Sales Across Brokerages

What cross-brokerage wash-sale monitoring should detect, explain, and record before and after a tax-loss trade.

Estate Planning With Tax-Loss Harvesting
June 14, 2025 · 6 min read

Estate Planning With Tax-Loss Harvesting

How tax-loss harvesting, cost basis, charitable planning, and the step-up in basis can interact in a long-term estate strategy.

Tax-Loss Harvesting With Stock-Based Compensation
June 3, 2025 · 6 min read

Tax-Loss Harvesting With Stock-Based Compensation

How RSU vesting, ESPP purchases, employer-stock concentration, cost basis, and wash sales affect a harvesting plan.

Liquidity From Concentrated Stock Without Selling Every Winner
May 27, 2025 · 4 min read

Liquidity From Concentrated Stock Without Selling Every Winner

How harvested losses can support selective gain realization and liquidity planning in a concentrated-stock portfolio.

Tax-Loss Harvesting During Sector Rotations
May 22, 2025 · 5 min read

Tax-Loss Harvesting During Sector Rotations

How sector rotations create loss lots—and how to preserve the investment plan when evaluating a replacement.

Married Couples and the Household Wash-Sale Rule
May 20, 2025 · 5 min read

Married Couples and the Household Wash-Sale Rule

Why a spouse's purchases, retirement accounts, dividend reinvestment, and equity awards belong in every household wash-sale review.

Tax Planning During a Job Transition
May 15, 2025 · 6 min read

Tax Planning During a Job Transition

How a job change or lower-income year can affect gain realization, loss harvesting, equity compensation, and estimated taxes.

Tax Moves Every Investor in Their 30s Should Know
May 6, 2025 · 6 min read

Tax Moves Every Investor in Their 30s Should Know

A practical order of operations for retirement accounts, taxable investing, equity compensation, tax lots, and loss harvesting.

The Future of Automated Tax Management
April 15, 2025 · 5 min read

The Future of Automated Tax Management

How tax software could evolve from loss alerts toward explainable, account-wide planning without removing investor control.

Tax-Loss Harvesting for Busy Professionals
April 8, 2025 · 5 min read

Tax-Loss Harvesting for Busy Professionals

A low-maintenance workflow for monitoring tax lots, approving trades, avoiding wash sales, and keeping records across accounts.

Tax-Loss Harvesting for Dividend Stocks
April 1, 2025 · 5 min read

Tax-Loss Harvesting for Dividend Stocks

How dividend reinvestment, qualified-dividend holding periods, tax lots, and replacement exposure affect loss harvesting.

Can Tax-Loss Harvesting Support Active Rebalancing?
March 18, 2025 · 5 min read

Can Tax-Loss Harvesting Support Active Rebalancing?

How realized losses can reduce the tax cost of rebalancing—without confusing tax efficiency with permission to take more risk.

Tax-Loss Harvesting in Volatile Markets
March 11, 2025 · 5 min read

Tax-Loss Harvesting in Volatile Markets

A disciplined process for evaluating loss lots, replacement exposure, wash-sale risk, and tax value during volatile markets.

Tax-Loss Harvesting for Young Investors
February 18, 2025 · 6 min read

Tax-Loss Harvesting for Young Investors

When harvesting helps a young taxable investor, when a lower tax bracket reduces its value, and why contributions and wash sales matter.

Carryforward Losses Explained: Unlocking Future Tax Savings
February 11, 2025 · 5 min read

Carryforward Losses Explained: Unlocking Future Tax Savings

How capital-loss carryforwards work, when they become useful, and how investors can apply unused losses in future tax years.

DIY Tax-Loss Harvesting vs. Automation: Two Case Studies
February 4, 2025 · 6 min read

DIY Tax-Loss Harvesting vs. Automation: Two Case Studies

Two case studies comparing manual tax-loss harvesting with automated monitoring, including missed lots and wash-sale risk.

Short-Term vs. Long-Term Capital Gains Tax
December 28, 2024 · 6 min read

Short-Term vs. Long-Term Capital Gains Tax

How holding periods determine short- or long-term treatment and why the distinction changes lot-selection decisions.

Why Retirement Accounts Don’t Benefit From Tax-Loss Harvesting
December 18, 2024 · 6 min read

Why Retirement Accounts Don’t Benefit From Tax-Loss Harvesting

Why IRA and 401(k) losses do not create current capital-loss deductions—and how retirement purchases can affect taxable-account wash sales.

Sector Swaps: How to Reinvest Smartly After Tax Loss Harvesting
November 26, 2024 · 4 min read

Sector Swaps: How to Reinvest Smartly After Tax Loss Harvesting

How sector swaps can preserve market exposure after a harvest without immediately repurchasing the sold security.

How to Avoid the Wash-Sale Rule
November 5, 2024 · 5 min read

How to Avoid the Wash-Sale Rule

A practical guide to the wash-sale window, replacement securities, recurring buys, spouse accounts, and rebuy timing.

Tax-Loss Harvesting Across Multiple Brokerage Accounts
October 1, 2024 · 7 min read

Tax-Loss Harvesting Across Multiple Brokerage Accounts

How to consolidate tax lots, gains, and purchase activity across brokerages before harvesting a loss.

AI for Crypto Tax-Loss Harvesting
June 11, 2024 · 3 min read

AI for Crypto Tax-Loss Harvesting

How automated lot tracking can identify crypto losses, coordinate gains, and preserve records across volatile digital-asset positions.

Machine Learning for Tax-Loss Harvesting
June 3, 2024 · 4 min read

Machine Learning for Tax-Loss Harvesting

How automated models can scan tax lots, compare gain offsets, and identify harvesting opportunities across complex portfolios.

Tax-Loss Harvesting Around Dividend Income
May 16, 2024 · 2 min read

Tax-Loss Harvesting Around Dividend Income

How dividend income, ex-dividend timing, capital losses, and carryforwards fit into one coordinated taxable-portfolio strategy.

Building a Tax-Aware Portfolio for Young Investors
May 14, 2024 · 2 min read

Building a Tax-Aware Portfolio for Young Investors

How young investors can automate lot tracking, harvesting checks, and wash-sale monitoring while keeping control of their portfolio.

Tax-Loss Harvesting for Young Investors
May 10, 2024 · 2 min read

Tax-Loss Harvesting for Young Investors

A practical introduction to building a taxable portfolio and using tax-loss harvesting early in an investor's compounding journey.

Tax-Loss Harvesting for Traders and Long-Term Investors
May 7, 2024 · 3 min read

Tax-Loss Harvesting for Traders and Long-Term Investors

Compare tax-loss harvesting for active traders and long-term investors, including holding periods, lot choice, and wash-sale exposure.

Navigating Taxes as a Self-Employed Worker: A Comprehensive Guide
April 30, 2024 · 2 min read

Navigating Taxes as a Self-Employed Worker: A Comprehensive Guide

Tax-planning considerations for self-employed investors, including variable income, estimated taxes, retirement accounts, and taxable gains.

Securing Your Children's Future: The Power of Trusts and Tax Planning
April 21, 2024 · 3 min read

Securing Your Children's Future: The Power of Trusts and Tax Planning

An introduction to trusts, gifting, investment taxation, and the planning questions families should review with qualified advisors.

Demystifying Tax Basis: Understanding Its Impact on Investments
March 28, 2024 · 3 min read

Demystifying Tax Basis: Understanding Its Impact on Investments

A clear explanation of tax basis, holding periods, realized gains, and why basis determines the tax result of an investment sale.

RSU Taxation: Vesting, Basis, and Capital Gains
March 24, 2024 · 2 min read

RSU Taxation: Vesting, Basis, and Capital Gains

How RSU vesting creates ordinary income and cost basis, and how later sales produce short- or long-term capital gains and losses.

The Pitfalls of Portfolio Rebalancing
March 20, 2024 · 2 min read

The Pitfalls of Portfolio Rebalancing

How rebalancing can create unnecessary taxable gains and how lot selection and loss offsets can improve the after-tax result.

Lot-Level Tax-Loss Harvesting: Why Specific Lots Matter
March 15, 2024 · 3 min read

Lot-Level Tax-Loss Harvesting: Why Specific Lots Matter

Why individual tax lots—not blended position returns—determine the gain, loss, holding period, and tax value of a sale.

ETFs vs Individual Stocks
March 13, 2024 · 3 min read

ETFs vs Individual Stocks

Compare ETFs and individual stocks through diversification, tax-lot flexibility, harvesting opportunities, and portfolio-maintenance tradeoffs.

Advanced Tax Reduction Strategies
March 8, 2024 · 2 min read

Advanced Tax Reduction Strategies

Advanced tax-reduction strategies for taxable investors, including loss harvesting, gain management, account coordination, and basis planning.

Taxes and Employee Stock Purchase Plans (ESPP)
February 9, 2024 · 2 min read

Taxes and Employee Stock Purchase Plans (ESPP)

How ESPP discounts, qualifying dispositions, cost basis, holding periods, and later sales affect an employee's tax result.

What Is Direct Indexing and How Does It Work?
February 9, 2024 · 5 min read

What Is Direct Indexing and How Does It Work?

Direct indexing holds individual stocks instead of an index fund. Learn how it works, where tax-loss harvesting fits, and when an overlay is different.

How TaxHarvest Saves You Money on Taxes
February 8, 2024 · 2 min read

How TaxHarvest Saves You Money on Taxes

How TaxHarvest finds lot-level losses, checks wash-sale risk, coordinates gains, and estimates the tax value before a trade.

Is Tax Loss Harvesting Worth It? A Decision Framework
February 6, 2024 · 7 min read

Is Tax Loss Harvesting Worth It? A Decision Framework

Tax loss harvesting is worth it when usable losses, tax rate, wash-sale control, and portfolio fit clear the hurdle. Use this decision framework before selling.