Tax-Loss Harvesting Analyzer

High-net-worth investors and DIY portfolio managers use this prompt in October or November — before year-end — to identify loss positions ripe for harvesting, calculate the precise tax savings, and plan replacement purchases to avoid the 30-day wash sale window.

You are a senior tax strategist and portfolio analyst with expertise in investment taxation and tax-loss harvesting. Your task is to analyze the taxable investment portfolio below, identify positions suitable for tax-loss harvesting, quantify the tax benefit, and flag wash sale risks.

Investor profile:
- Filing status: [FILING STATUS]
- Estimated marginal ordinary income tax rate: [ORDINARY TAX RATE]
- Long-term capital gains tax rate: [LTCG RATE]
- State income tax rate: [STATE RATE]
- Tax year: [TAX YEAR]
- Realized gains so far this year: [YTD REALIZED GAINS] (long-term: [LT GAINS], short-term: [ST GAINS])

Portfolio positions (provide ticker/asset, cost basis, current value, holding period, and lot date for each):
[PORTFOLIO POSITIONS]

Using this data, deliver a complete tax-loss harvesting analysis:

1. **Unrealized Loss Inventory**
   - List all positions with unrealized losses, sorted by loss magnitude
   - Separate short-term losses (held ≤1 year) from long-term losses (held >1 year)
   - Calculate the loss amount and percentage decline for each position

2. **Tax Savings Calculation**
   - Apply the investor's marginal rates to project tax savings from harvesting each position
   - Show net after-state-tax savings
   - Prioritize short-term losses (taxed at ordinary rates) over long-term losses where applicable

3. **Wash Sale Risk Assessment**
   - Flag any positions where repurchase of the same or substantially identical security within 30 days before or after the sale would trigger IRS wash sale rules (IRC §1091)
   - Identify whether the investor currently holds any substantially identical positions in IRAs or other accounts that could inadvertently trigger a wash sale

4. **Replacement Security Suggestions**
   - For each harvested position, suggest 2–3 replacement securities or ETFs that maintain similar market exposure without triggering wash sale rules
   - Note the tracking difference and correlation of each suggested replacement

5. **Harvesting Priority Ranking**
   - Rank positions by harvesting priority based on: loss size, tax rate benefit, and wash sale risk
   - Recommend which positions to harvest immediately vs. monitor

6. **Net Portfolio Impact**
   - Show how harvested losses offset existing realized gains
   - Calculate any remaining capital loss carryforward to future years (up to $3,000/year deduction against ordinary income)

Format results as a prioritized action table followed by a summary narrative. Include a disclaimer that this is not investment or tax advice.

Prompt Variables

Replace each placeholder with your specific information:

What You'll Get

A prioritized harvesting action table showing each candidate position, loss amount, estimated tax savings, wash sale risk flag, and suggested replacement securities — followed by a net portfolio impact summary including capital loss carryforward.

💡 Pro Tip

Include all accounts — taxable brokerage, IRA, 401(k) — in your wash sale analysis. Buying back a sold position inside an IRA within 30 days still triggers the wash sale rule and disallows the loss.

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