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:

Largest absolute loss (biggest tax benefit)
Short-term losses first (offset short-term gains taxed at ordinary income rates)
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