Tax-Loss Harvesting

Scan taxable accounts for unrealized losses and generate a wash-sale-compliant harvest plan.

1|Updated May 16, 2026
One-click install
npx skills add https://github.com/executiveusa/Cheggie-trade-V2 --skill tax-loss-harvesting-executiveusa
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: Tax-Loss Harvesting
Source: https://github.com/executiveusa/Cheggie-trade-V2/tree/main/core/financial-skills/plugins/vertical-plugins/wealth-management/skills/tax-loss-harvesting
Command: npx skills add https://github.com/executiveusa/Cheggie-trade-V2 --skill tax-loss-harvesting-executiveusa

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

It helps investors identify unrealized losses in taxable accounts and turn them into potential tax savings while avoiding wash-sale violations.

Core Features & Use Cases

  • Candidate Detection & Prioritization: Scans taxable positions for unrealized losses and prioritizes the biggest absolute losses, short-term losses first, and larger % losses.
  • Tax Budgeting & Savings Estimation: Computes realized gains/losses YTD, incorporates carryforwards, and estimates tax savings using marginal ordinary income and capital gains rates (including the $3,000 net loss deduction concept).
  • Replacement Security & Wash Sale Management: Suggests replacement securities with similar exposure that are not substantially identical, then checks 30-day lookback/forward across the household (including DRIPs) and produces an execution plan plus post-harvest tracking outputs.

Use Case Example: Before year-end, you want a report and trade plan for harvesting losses across multiple taxable accounts without triggering wash sales, while maintaining market exposure via replacement ETFs.

Quick Start

Use the Tax-Loss Harvesting skill to generate a harvest opportunity list with estimated tax savings, a replacement trade plan, and a wash-sale tracking calendar for your taxable accounts.

Frequently Asked Questions about Tax-Loss Harvesting

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I identify tax-loss harvesting opportunities in my taxable accounts?

Tax-loss harvesting works by selling securities at a loss to offset capital gains and up to $3,000 of ordinary income. It estimates tax savings by computing realized YTD gains/losses, incorporating carryforwards, and applying marginal tax rates to the net results.

How do I avoid wash sales when replacing harvested securities?

To avoid wash sales when replacing harvested securities, select replacement securities with similar market exposure that are not substantially identical, then validate a 30-day lookback and forward window across the entire household, including DRIPs.

Can I calculate estimated tax savings from harvesting unrealized losses?

You can calculate estimated tax savings from harvesting unrealized losses by computing realized gains and losses year-to-date, applying capital loss carryforwards, and using marginal ordinary income and capital gains rates, including the $3,000 net loss deduction.

What is the best way to maintain market exposure during tax-loss harvesting?

The best way to maintain market exposure during tax-loss harvesting is to execute a replacement trade plan using similar but not substantially identical ETFs, ensuring continuous market participation while capturing tax losses and tracking post-harvest positions.

Does tax-loss harvesting work for ongoing portfolio rebalancing or only year-end planning?

Tax-loss harvesting works for both year-end tax planning and ongoing taxable-account rebalancing workflows. It continuously scans for unrealized losses, prioritizes short-term and large percentage drops, and produces an execution plan with replacement rationales.