Wash Sale Rules for Options Traders: The Complete Guide

The wash sale rule is one of the most misunderstood parts of options trading taxes.

Here's the basic rule:

If you sell a security at a loss, you can't deduct that loss if you buy the same (or substantially identical) security within 30 days before or 30 days after the loss.

For options traders, this creates a minefield. Selling cash-secured puts, rolling positions, and harvesting losses all trigger wash sale risks.

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This guide walks through real scenarios and shows you exactly how to avoid the trap.

The Wash Sale Rule: Basic Mechanics

The wash sale rule applies to sales at a loss. It doesn't apply to gains.

The 61-day window:

• 30 days before the loss sale
• The loss sale date
• 30 days after the loss sale

Within this window, you can't buy substantially identical securities.

If you do:

• The loss is disallowed (you can't deduct it)
• Your basis in the new shares is increased by the disallowed loss
• The loss is deferred until you sell the new shares

Real Example: Simple Wash Sale

• 1/15/2025: Buy 100 SPY at $420/share (cost: $42,000)
• 2/20/2025: Sell 100 SPY at $400/share (loss: -$2,000)
• 2/21/2025: Buy 100 SPY at $395/share (cost: $39,500)

Analysis:

Date	Action	Days from Loss Sale
1/15	Buy 100 SPY @ $420	-36 days (within 30-day window)
2/20	Sell 100 SPY @ $400 (LOSS)	0
2/21	Buy 100 SPY @ $395	+1 day (within 30-day window)

Wash sale triggers:

• You sold at a loss (2/20)
• You bought within 30 days after (2/21)
• The -$2,000 loss is disallowed

Tax consequences:

• Your new basis in the 100 shares: $39,500 + $2,000 (disallowed loss) = $41,500
• You've deferred the loss until you sell these shares
• If you sell the new shares at $395, you realize only -$1,500 loss (the $2,000 is deferred)

When Wash Sale Rules Apply to Options Traders

Options traders hit wash sale rules in three main scenarios:

Scenario 1: Selling Puts and Buying Stock

You sell a cash-secured put expecting it to expire worthless. It gets assigned (you buy stock at the strike price). Later, you sell that stock at a loss.

Example:

• 1/15/2025: Sell 100 SPY $400 puts for $2.00 premium
• 1/20/2025: Assigned; you buy 100 SPY at $400/share
• 1/21/2025: SPY drops; you sell the stock at $390/share (loss: -$1,000)
• 1/22/2025 - 2/20/2025: You decide to buy 100 SPY again at a better entry point

Wash sale analysis:

The loss sale (1/21) is within 30 days of:

• Put sale (1/15) = before the sale
• Put assignment (1/20) = before the sale

When you buy again after 1/21, you're within the 30-day window.

Result: Your -$1,000 loss is disallowed. Your new cost basis is increased by $1,000.

Scenario 2: Rolling Positions

You sell a call spread at a loss. You immediately buy back the spread and open a new one.

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Example:

• 1/1/2025: Sell a call spread (short $450 call, long $460 call) for $1.00 credit
• 1/15/2025: Stock drops; spread is worth $0.20. You buy back for a loss: $1.00 sold, $0.20 closed = -$0.80 loss (-$80)
• 1/16/2025: You sell a new call spread (short $445 call, long $455 call) for $0.90 credit

Wash sale analysis:

Is the new spread "substantially identical" to the old spread?

No. Spreads with different strikes are considered different securities. So wash sale rules don't apply here.

But: If you sold a call spread (short $450 call) at a loss and bought back the exact same $450 call at a loss, then immediately sold the same $450 call again, wash sale might trigger.

Key distinction:

• Different strikes = No wash sale
• Same strike, same expiration, bought and immediately resold = Possible wash sale

Scenario 3: Tax Loss Harvesting in a Stock Position

You own 100 shares of a stock at a loss. You want to harvest the loss for taxes but keep market exposure.

Example:

• 1/15/2025: Buy 100 AAPL at $200/share
• 1/31/2025: AAPL is at $180/share; you sell at loss (-$2,000)
• 2/1/2025: You sell a call spread on AAPL to maintain exposure (instead of buying stock)
• 2/15/2025: You reconsider and buy 100 AAPL at $175/share

Wash sale analysis:

• Sold at loss: 1/31
• Bought AAPL calls within 30 days after: 2/1
• Bought AAPL stock within 30 days after: 2/15

Question: Do call options trigger wash sale rules?

IRS position: Selling calls (not buying) does NOT trigger wash sale. But buying calls within 30 days of selling stock at a loss might.

The IRS has stated that buying call options (even out-of-the-money) can trigger wash sale rules because they provide downside protection similar to still owning the stock.

Conservative rule: If you sell a stock at a loss, don't buy calls or buy stock within 30 days before or after.

Options and Wash Sales: The Gray Area

The IRS has issued mixed guidance on whether options trigger wash sale rules.

Official Guidance (and Common Misunderstandings)

IRS Notice 2008-70 addressed wash sale rules and options, stating:

1. Buying calls to replace a sold stock: Can trigger wash sale if calls provide substantial downside protection
2. Selling calls: Does NOT trigger wash sale (you're not replacing the position)
3. Selling puts: Might trigger wash sale if you buy stock within 30 days (the assignment counts as a purchase)

In practice:

• Buying protective puts: Likely triggers wash sale (you're insuring against loss)
• Selling puts: Triggers wash sale IF assigned and you later sell the stock at a loss
• Selling calls: Does NOT trigger wash sale

Real Example: Buying Protective Puts

• 1/15/2025: Buy 100 AAPL at $200/share
• 2/1/2025: AAPL drops to $180/share
• 2/1/2025: You realize you should have sold, but instead buy a $180 protective put
• 2/10/2025: You decide to sell the 100 AAPL at $180 (loss: -$2,000)
• 2/11/2025: AAPL drops further; you regret selling and buy 100 AAPL at $170

Analysis:

When you bought the protective put (2/1), you replaced the sold position with a synthetic long position (stock + put = protected long).

Wash sale question: Does buying the put trigger wash sale on the later stock loss?

IRS answer: Possibly. The put provides downside protection equivalent to still owning the stock. The wash sale rule's intent is to prevent people from selling losses and immediately re-acquiring "substantially identical" positions. Buying a protective put is arguably re-acquiring economic exposure.

Practical result: The IRS would likely disallow the -$2,000 loss.

Real Example: Selling Puts at a Loss

• 1/1/2025: Sell 1 SPY $410 put for $2.00 (credit: $200)
• 1/31/2025: SPY drops to $390; put is worth $20 (intrinsic value $20 + time value $0)
• 2/1/2025: You buy back the put for $20 (loss: $2.00 - $0.20 = $1.80, or -$180)
• 2/2/2025: You sell the same $410 put again for $1.50 credit

Analysis:

You sold a put at a loss ($180 loss) and immediately sold the same put again at a similar strike.

Wash sale question: Does this trigger wash sale?

IRS answer: No, probably not. You're selling (not buying) the same instrument. Wash sale rules apply to disallowed losses, not to re-entering the same trade.

But: The IRS might argue that the $180 loss is premature (the position wasn't truly closed; you immediately re-entered it). This is more of a "substance over form" argument than wash sale.

Real Example: Assigned Puts and Later Sale at Loss

• 1/1/2025: Sell 1 SPY $410 put for $2.00 (credit: $200)
• 1/15/2025: Assigned; you buy 100 SPY at $410/share (cost: $41,000)
• 2/1/2025: SPY is at $400; you sell 100 SPY for loss (-$1,000)
• 2/2/2025: SPY drops further; you buy 100 SPY at $395/share

Wash sale analysis:

• Sold at loss: 2/1
• Bought substantially identical: 2/2 (within 30 days)
• Previous buy (assignment): 1/15 (within 30 days BEFORE the loss sale)

Wash sale triggers:

• The assignment (1/15) is within 30 days before the loss sale (2/1)
• The new purchase (2/2) is within 30 days after
• Your -$1,000 loss is disallowed

The -$1,000 loss is added to the cost basis of the shares purchased on 2/2. Your new basis: $39,500 + $1,000 = $40,500.

How to Avoid Wash Sale Problems

Rule 1: Track the 61-Day Window Carefully

Create a spreadsheet:

Date	Action	Notes
1/15	Sell AAPL 100 @ $180 (loss: -$2,000)	Loss sale date
1/16-2/14	Can't buy AAPL or call options	30 days after = 2/14
2/15	Earliest date to buy AAPL	31 days after = 2/15

Be conservative: Many traders use 31 days after (not 30) to be safe.

Rule 2: Don't Use Protective Puts After a Loss

If you're going to harvest a tax loss, don't buy protective puts to stay in the trade.

Instead:

• Sell the stock at a loss
• Wait 31 days
• Buy the stock back (or protective puts)
• Then you've reset the clock

Rule 3: After Selling at a Loss, Avoid Related Options

After selling a stock at a loss:

Action	Within 30 Days After Loss Sale?	Wash Sale Risk?
Buy call options on same stock	Within window	HIGH RISK (downside protection)
Buy protective puts on same stock	Within window	HIGH RISK
Sell covered calls on same stock	Within window	LOW RISK (but avoid if re-buying soon)
Trade options on different stock	Within window	NO RISK
Roll uncovered calls	Within window	LOW RISK (unless you're re-acquiring stock)

Conservative approach: After a loss sale, wait 31 days before trading options on the same underlying.

Rule 4: Track Put Assignments Carefully

If you sell puts and get assigned, you've bought stock at the strike price. If you later sell that stock at a loss, wash sale rules apply to all buys within 30 days before and after the loss sale.

Example to avoid:

• 1/1/2025: Sell puts, assigned 1/10/2025 (stock cost: $410)
• 1/25/2025: Sell stock at $400 (loss: -$1,000)
• 1/26/2025: DON'T buy the stock again
• 2/15/2025: NOW you can buy

When to break this rule:

• If you didn't know wash sale rules (defer compliance)
• If the loss is small enough that deferral is acceptable
• If the IRS is unlikely to audit you

Using Losses Strategically (While Respecting Wash Sales)

Strategy 1: Harvest Losses, Then Wait 31 Days

• 1/15: Sell a losing position
• 1/16-2/14: Don't buy back (avoid wash sale)
• 2/15: Buy back with full loss deduction taken for 2024 taxes
• Can use loss to offset gains or reduce income by $3,000 (or carry forward)

Strategy 2: Use Loss Harvesting to Offset Gains

If you have a profitable call spread and a losing stock position:

• Sell the stock at a loss (harvest: -$2,000)
• Use the loss to offset call spread gain of +$2,000
• Net: $0 taxable gain (no capital gains tax)
• Don't re-buy the stock for 31 days

Strategy 3: Use Different Securities to Stay in the Trade

If you sell SPY at a loss and want to stay exposed to the S&P 500:

• Sell 100 SPY at a loss (harvest: -$2,000)
• Wait 31 days
• Buy 100 IVV or VOO (similar S&P 500 ETF)
• Not a wash sale (different securities; SPY and IVV are not "substantially identical")

But: Some tax professionals argue that buying a different S&P 500 ETF might still be considered "substantially identical" for wash sale purposes.

Conservative approach: Wait 31 days and buy the same security back, or use a different asset class entirely.

Strategy 4: Use Call Spreads to Replace a Sold Position

If you sell a stock at a loss and want market exposure:

• Sell stock at loss (harvest: -$2,000)
• Sell call spreads on the same stock (short $450 call, long $460 call)
• Wait 31 days
• Buy stock back if you want

Is this a wash sale?

Selling calls (not buying) does NOT create a wash sale. You're not re-acquiring the position immediately.

But some tax professionals would argue that selling call spreads (especially if sold for a net credit and structured as a synthetic long) might trigger wash sale.

Conservative approach: Wait 31 days if possible. The tax savings aren't worth the audit risk.

Tracking Wash Sales on Your Tax Return

If Wash Sale Happens (and is disallowed by IRS)

You'll see a wash sale adjustment on your 1099-B from your broker:

Box 3 on 1099-B: "Wash sale loss disallowed"

The IRS will also send you a notice of the disallowance.

How to Handle It on Form 8949

When filing taxes, you report the wash sale loss disallowance on Form 8949:

1. List the loss sale
2. Box "Wash sale loss disallowed": Enter the disallowed amount
3. The disallowed loss is added to the cost basis of the new purchase

How to Adjust Your Basis in Tax Software

TurboTax:

1. Go to Investment Income → 1099-B Sales
2. Import your 1099-B data
3. For each wash sale entry, TurboTax will ask if you made a wash sale purchase
4. Adjust basis accordingly

H&R Block: Similar process through Investment Income → 1099-B Data

Common Wash Sale Mistakes

Mistake 1: Selling a Call Spread at a Loss, Then Buying Back the Short Call

• Sell $450/$460 call spread for $1.00 (net credit: $100)
• Stock drops; spread is now worth $0.30 (you could close for -$0.70 loss = -$70)
• You buy back the short $450 call at $0.50 (loss: $1.00 sold, $0.50 closed = gain $0.50, not a loss)
• BUT your long call is still open

Wash sale analysis:

• You haven't realized a loss on the spread (the net P&L is a loss, but buying back only half the spread doesn't lock in a loss)
• No wash sale trigger

But if you buy back the entire spread at a loss and immediately sell it again at a similar price:

• Possible wash sale (you're reselling the same spread immediately)

Mistake 2: Selling Stock at a Loss, Then Opening a Buy-Write (Stock + Call)

• 1/15: Sell 100 AAPL at $180 (loss: -$2,000)
• 1/16: Open a buy-write: Buy 100 AAPL at $175 + sell $180 call for $2.00

Wash sale analysis:

You bought back AAPL within 30 days of selling at a loss = WASH SALE TRIGGERED.

The short call (sold for $2.00) doesn't exempt you from wash sale. You've re-acquired the stock.

Correct approach:

• Sell stock at loss (1/15)
• Wait 31 days (until 2/15)
• Open buy-write (2/15)

Mistake 3: Forgetting About Put Assignments in Your 30-Day Count

• 1/1: Sell puts; assigned 1/5 (buy 100 shares)
• 1/20: Sell shares at loss
• 1/21: Buy shares again

Wash sale analysis:

• Assignment date (1/5) is within 30 days before the loss sale (1/20)
• New purchase (1/21) is within 30 days after
• WASH SALE TRIGGERED

All three events (assignment, loss sale, re-purchase) are within the 61-day window.

Wash Sales and Multiple Positions

If you own multiple positions in the same stock at different cost bases, wash sale rules track separately for each cost lot.

Example:

• Lot A: 100 AAPL bought at $200/share (Jan)
• Lot B: 100 AAPL bought at $190/share (Feb)
• 2/15: Sell Lot A at $185 (loss: -$1,500)
• 2/16: Buy 100 AAPL at $180 (within 30 days)

Analysis:

• Loss: -$1,500 on Lot A
• New purchase: 100 shares on 2/16
• Wash sale applies to the new purchase: Cost basis becomes $180 + $1,500 (deferred loss) = $1,680 per share

The new shares are treated as a replacement for Lot A.

Bottom Line: Avoiding Wash Sale Trap

Key takeaways:

1. Don't sell at a loss and buy back within 30 days

   • The 30 days: Before loss sale and after
   • Total: 61-day window

2. Put assignments count as purchases

   • If assigned on 1/15 and you later sell at a loss on 1/20, the assignment is within 30 days before
   • Don't buy back that stock within 30 days after 1/20

3. Buying calls/puts after a loss sale is risky

   • Protective puts: Definitely risky (downside protection)
   • Call options: Risky if they replace stock exposure
   • Covered calls: Safer (you're not buying back exposure)

4. Use different securities to stay invested

   • Sell SPY at a loss
   • Wait 31 days
   • Buy VTI or VOO (different S&P 500 ETFs)
   • Not a wash sale (different securities)

5. Track wash sales on Form 8949

   • Report disallowed loss
   • Add to cost basis of new purchase
   • This defers the loss until you sell the new position

6. Conservative rule: Wait 31 days after a loss

   • If you're unsure, wait
   • The tax savings aren't worth an audit
   • You can always defer the loss to next year

7. For options traders: Monitor put assignments

   • Assignment = purchase at strike price
   • If you later sell at a loss, watch the 30-day window before and after assignment

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