Tax-Loss Harvesting

description: Identify tax-loss harvesting opportunities across taxable accounts. Finds positions with unrealized losses, suggests replacement securities, and tracks wash sale windows. Triggers on “tax-loss harvesting”, “TLH”, “harvest losses”, “tax losses”, “unrealized losses”, or “year-end tax planning”.

Workflow

Step 1: Identify Candidates

Scan taxable accounts for positions with unrealized losses:

Security	Asset Class	Cost Basis	Current Value	Unrealized Loss	Holding Period	% Loss
					ST / LT

Prioritize by:

1. Largest absolute loss (biggest tax benefit)
2. Short-term losses first (offset short-term gains taxed at ordinary income rates)
3. Positions with the largest % loss (less likely to recover quickly)

Step 2: Gain/Loss Budget

Calculate the client’s tax situation:

Category	Amount
Realized short-term gains YTD
Realized long-term gains YTD
Realized losses YTD
Net gain/(loss) position
Carryforward losses from prior years
Target harvesting amount

Tax savings estimate:

• Short-term losses × marginal ordinary income rate
• Long-term losses × capital gains rate
• Up to $3,000 net loss deduction against ordinary income
• Excess carries forward

Step 3: Replacement Securities

For each harvest candidate, suggest a replacement that:

• Maintains similar market exposure (same asset class, sector, geography)
• Is NOT “substantially identical” (wash sale rule)
• Has similar risk/return characteristics

Sell	Replace With	Reason	Tracking Error Risk
SPDR S&P 500 (SPY)	iShares Core S&P 500 (IVV)	Same index, different fund family	Minimal
Vanguard Total Intl (VXUS)	iShares MSCI ACWI ex-US (ACWX)	Similar exposure, different index	Low
Individual stock ABC	Sector ETF (XLK)	Broader exposure, no wash sale risk	Moderate

Step 4: Wash Sale Check

Before executing, verify no wash sales:

• Check ALL accounts in the household (taxable, IRA, Roth, spouse accounts)
• 30-day lookback: Did we buy substantially identical securities in the last 30 days?
• 30-day forward: Block repurchase of the same security for 30 days
• Check for dividend reinvestment plans (DRIPs) that could trigger wash sales
• Document the wash sale window for each trade

Security Sold	Wash Sale Window Start	Window End	DRIP Active?	Risk

Step 5: Execution Plan

Trade #	Account	Action	Security	Shares	Est. Proceeds	Est. Loss	Replacement	Notes
		Sell
		Buy

Summary:

• Total estimated losses harvested: $
• Estimated tax savings: $ (at marginal rate of %)
• Net portfolio impact: minimal (replacement securities maintain exposure)
• Wash sale window management: [dates]

Step 6: Post-Harvest Tracking

After 30+ days, optionally:

• Swap back to original securities (if preferred)
• Maintain replacement securities (if no reason to switch back)
• Update cost basis records
• Document for tax reporting

Step 7: Output

• Harvest opportunity list (Excel)
• Trade execution sheet
• Wash sale tracking calendar
• Tax savings estimate summary
• Replacement security rationale

Important Notes

• Wash sale rules are strict — violations disallow the loss AND adjust cost basis
• Substantially identical means same security, not same asset class — ETFs tracking different indexes are generally fine
• Always coordinate across all household accounts including retirement accounts
• Consider the long-term cost basis step-down — harvesting resets cost basis, which means more gains later
• Year-end is prime harvesting season but opportunities exist throughout the year
• Mutual fund capital gains distributions in December can create additional harvesting urgency
• Document everything for tax reporting and compliance
• Not all losses are worth harvesting — transaction costs and tracking error have real costs