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AI agent for portfolio managers

Tax-Loss Harvesting Opportunity Agent

Find valid tax-loss harvests with replacements that keep client exposure.

Tax-Loss Harvesting Opportunity Agent: what goes in, what the agent does and what you get

What it does

Selling a position at a loss can lower a client's tax bill, but the opportunity vanishes with the next rally and a wash-sale mistake can cancel the benefit. This agent reads client holdings and tax lots, finds lots with losses above a threshold, and checks for wash-sale conflicts across all accounts of the household, including recent buys and reinvested dividends. It then picks replacement securities that keep the exposure without being substantially identical, and drafts a proposal showing the estimated tax value. Before presenting, it rechecks current prices. If a loss has shrunk below the threshold, it drops the case. The advisor approves every trade.

How it works

Follow the arrows from top to bottom. The orange dashed arrow is the loop: when a check fails, the agent goes back and tries again.

Start and resultWhat it doesA check on its own workWaits for your OKGoes back and retries
Yes, continueYes, continueApprovedNoNo 1 STARTS WHEN Weekly or market drop trigger 2 USES A TOOL Read holdings, tax lots and recent household trades 3 DOES List lots with losses above the threshold 4 DOES Check wash-sale conflicts across accounts andreinvestments 5 CHECKS THE RESULT Is each sale free of wash-sale conflict? If not: drop the lot or move the sale date and recheck.Back to step 3. 6 DOES Select replacement securities that are notsubstantially identical 7 USES A TOOL Refresh prices before proposing 8 CHECKS THE RESULT Is the loss still above the threshold at currentprices? If not: drop the case and note the change. Back to step3. 9 DOES Draft the proposal with estimated tax value andtracking difference 10 YOU APPROVE Advisor approves every trade 11 RESULT Approved harvest list and wash-sale watch dates
Read the steps as a list
  1. Weekly or market drop trigger
  2. Read holdings, tax lots and recent household trades
  3. List lots with losses above the threshold
  4. Check wash-sale conflicts across accounts and reinvestments
  5. Is each sale free of wash-sale conflict?If not: drop the lot or move the sale date and recheck. Back to step 3.
  6. Select replacement securities that are not substantially identical
  7. Refresh prices before proposing
  8. Is the loss still above the threshold at current prices?If not: drop the case and note the change. Back to step 3.
  9. Draft the proposal with estimated tax value and tracking difference
  10. Advisor approves every tradeThe agent waits here for your OK.
  11. Approved harvest list and wash-sale watch dates

How it decides

It proposes a sale only when the net loss exceeds the threshold, no wash-sale conflict exists, and a suitable replacement is available.

  • Harvest only if the loss exceeds $1,000 and 5 percent of the lot
  • Check 30 days before and after the sale in all household accounts
  • Choose replacements from the approved list with similar exposure
  • Value the tax benefit using the client's marginal rate

Make it yours

Every agent is a starting point. You choose these settings for your own situation.

  • Loss threshold (default $1,000 and 5 percent)
  • Approved replacement list
  • Client tax rates
  • Run schedule

What keeps you in control

It always asks you first

  • Advisor approves every trade
  • Advisor approves the replacement security

Hard limits

  • Never places a trade
  • Does not give tax advice, advisor confirms with the client's accountant

It stops when

  • Done: proposals approved and wash-sale dates recorded
  • Stop: tax lot data is incomplete for the account

Set it up

We guide you through the set-up, step by step

Members get the full set-up guide for this agent. No technical skills needed: you copy, paste and upload.

10 minto set it up in your AI
5 AIsChatGPT, Claude, Copilot, Gemini, Grok
  • One set of instructions to paste into your AI, with the clicks for ChatGPT, Claude, Microsoft 365 Copilot, Gemini and Grok
  • The agent then walks you through connecting your own data, one source at a time
  • A downloadable copy with the flow chart, the rules and the full guide
Get access to this agent

An example run

What happensThe agent found 9 lots with losses, led by a $14,200 loss in a small-cap fund. A check found the client's spouse bought the same fund in an IRA 12 days earlier, a conflict. It dropped that lot but kept three others. After refreshing prices, one loss fell from $2,300 to $700 and was removed. The advisor approved 2 trades.

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