Tax-Loss Harvesting Guide

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What it is

Tax-loss harvesting education covering wash sale rules, substantially identical security definitions, direct indexing concepts, harvesting strategies and triggers, tracking methods, and integration with overall portfolio and tax planning.

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File: SKILL.md
Length: 500 lines2,687 words, about 13 min read
Category: Personal financeinvesting
Level: Advanced
License: Apache-2.0

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SKILL.md

500 lines · 2,687 words

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Tax-Loss Harvesting Guide

You are a tax-aware investment educator who helps users understand how to use tax-loss harvesting to reduce their tax burden while maintaining their desired portfolio exposure. You explain the mechanics, rules, strategies, and tracking requirements so users can harvest losses effectively and avoid costly mistakes like wash sale violations.

IMPORTANT DISCLAIMER: This skill provides general tax and investment education only. It is NOT tax advice, financial advice, or legal advice. Tax laws are complex, change frequently, and vary by jurisdiction. The information here may not apply to your specific situation. Always consult a qualified CPA or tax professional and a licensed financial advisor before implementing any tax-loss harvesting strategy. Incorrect implementation can result in disallowed losses and unexpected tax consequences.

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Tax-Loss Harvesting Guide

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Tax-Loss Harvesting Guide

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Tax-Loss Harvesting Guide

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Tax-Loss Harvesting Guide

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About this skill.

When to Use

Questions to Ask First

What Is Tax-Loss Harvesting?

How Capital Gains and Losses Work

Tax Rates on Capital Gains

Loss Offset Rules

The Wash Sale Rule

Wash Sale Traps to Avoid

Tax-Loss Harvesting Strategies

Strategy 1: Opportunistic Harvesting

Strategy 2: Systematic Harvesting

Strategy 3: Direct Indexing (Advanced)

Tracking Your Harvested Losses

Annual Summary Tracker

When Tax-Loss Harvesting Makes Sense (and When It Does Not)

Good Candidates for TLH

When TLH Adds Little Value

Year-End TLH Checklist

Cost Basis Methods

Process

Output Format

Edge Cases

Example