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Tax-Loss Harvesting Analyzer

Que fait ce prompt ?

Les investisseurs fortunés et les gestionnaires de portefeuille autonomes utilisent ce prompt en octobre ou novembre — avant la fin d'année — pour identifier les positions en perte à réaliser, calculer les économies fiscales exactes et planifier les rachats pour éviter la fenêtre de 30 jours de la règle wash sale.

Prompts

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.

Variables du Prompt

Remplacez chaque placeholder par vos informations spécifiques :

[FILING STATUS]
[ORDINARY TAX RATE]
[LTCG RATE]
[STATE RATE]
[TAX YEAR]
[YTD REALIZED GAINS]
[LT GAINS]
[ST GAINS]
[PORTFOLIO POSITIONS]

Ce que vous obtiendrez

Un tableau d'actions de récolte prioritaires indiquant pour chaque position candidate : le montant de la perte, les économies fiscales estimées, l'indicateur de risque wash sale et les remplacements suggérés — suivi d'un résumé de l'impact net sur le portefeuille incluant le report de perte en capital.

💡 Conseil d'Expert

Incluez tous les comptes — courtage imposable, IRA, 401(k) — dans votre analyse wash sale. Racheter une position vendue dans un IRA dans les 30 jours déclenche toujours la règle wash sale et invalide la perte.

Outils IA Compatibles

Claude

Best for structured multi-step analysis with detailed wash sale rule explanations. Use a Project to store the portfolio baseline and update it throughout the year as market conditions change.

ChatGPT

Use GPT-4o with Code Interpreter to run the actual tax savings calculations and sort positions by harvesting priority. Can also generate charts showing loss magnitude by position.

Gemini

Useful for identifying current replacement ETF options with live market data. Gemini can search for funds with high correlation to the harvested position to minimize tracking error during the wash sale window.

Perplexity

Ideal for researching the latest IRS wash sale rule interpretations and finding real-time replacement security options. Use it to verify that a proposed replacement ETF is not considered substantially identical to the sold position.

Ressources Associées

calculatorTax Calculator
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