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Introduction
1. Strategies
2. Customer accounts
3. Rules & regulations
3.1 Registration & reporting
3.2 The market
3.3 Options contracts
3.4 Taxation
3.4.1 Basic rules
3.4.2 Advanced rules
3.5 Public communications
3.6 Other rules & regulations
Wrapping up
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3.4.1 Basic rules
Achievable Series 9
3. Rules & regulations
3.4. Taxation

Basic rules

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You learned several options strategies in the strategies unit. This chapter focuses on the basic tax consequences of options.

The topics here assume you already know how options work. If you need a refresher on strategies, use the link above.

We’ll cover tax consequences related to:

  • Expiration
  • Trading
  • Exercise

Expiration

When an investor buys or sells an option, there are three potential outcomes:

  • Expiration
  • Trading the contract (closing out)
  • Exercise

Here, we’ll focus on expiration.

When an options contract expires, the tax result is a capital gain or loss equal to the premium. In other words, the entire premium is recognized as a gain or loss at expiration.

An investor goes long 1 ABC Jan 50 call at $4 when ABC’s market price is $51. Several months later, the ABC’s market price falls to $49 and stays there until expiration. What is the tax consequence?

Can you figure it out?

(spoiler)

Answer = $400 capital loss

The investor bought a call, and it expires out of the money (no intrinsic value). Calls expire if the market price is below the strike price at expiration.

The investor paid $4 per share ($400 total) and the option expires worthless, so they realize a $400 capital loss.

Let’s try another example:

One August 80 put is written for a premium of $7 when the underlying stock’s market price is $78. Just prior to expiration, the stock’s market price rises to $90. What is the tax consequence?

(spoiler)

Answer = $700 capital gain

The investor wrote (sold) a put, and it expires out of the money (no intrinsic value). Puts expire if the stock’s market price is above the strike price at expiration.

The investor received $7 per share ($700 total) and the option expires unexercised, so they realize a $700 capital gain.

Sidenote
Timing of tax reporting

A capital gain or loss related to an option expiration is reported to the Internal Revenue Service (IRS) in the year the option expires.

For example, suppose an investor goes short an option and receives a premium in December 2025, and the option expires in July 2026. Even though the premium was received in 2025, the premium income is reported on the investor’s 2026 tax return.

Trading

Before an option is exercised or expires, an investor can trade out (close out) of the position. This concept was covered in the issuance & the market chapter.

From a tax perspective, closing out creates a capital gain or loss equal to the contract’s overall gain or loss (what you paid versus what you received when you closed).

An investor goes long 1 XYZ Dec 35 put at $5 when XYZ’s market price is $36. XYZ’s market price falls to $32, and the investor closes the contract at intrinsic value. What is the tax consequence?

(spoiler)

Answer = $200 capital loss

To find the gain or loss, compare:

  • The premium paid to open the position, and
  • The premium received when the position is closed.

The put cost $5 per share ($500 total). When the stock falls to $32, the put is in the money by $3, so the investor closes the position by selling the option for $3 per share ($300 total).

Buying for $500 and later selling for $300 results in a $200 capital loss.

One more example:

A client of yours writes 1 ZZZ Sep 60 call for a premium of $4. A few months later, the investor closes the position at $3. What is the tax consequence?

(spoiler)

Answer = $100 capital gain

The client initially wrote (sold) the call for $4 per share ($400 total). To close a short option position, the client must buy it back. They close by purchasing the option for $3 per share ($300 total).

Selling for $400 and later buying back for $300 results in a $100 capital gain.

Exercise

Taxes related to exercising options are more complicated than expiration or trading.

Instead of creating an immediate capital gain or loss on the option itself, an exercise adjusts the tax numbers on the underlying security (usually stock). Specifically, exercise establishes either:

  • Cost basis (the total cost to buy the shares), or
  • Sales proceeds (the total amount received when the shares are sold).

Which one you establish depends on what happens to the stock at exercise:

  • If the exercise results in buying shares, you establish cost basis.
  • If the exercise results in selling shares, you establish sales proceeds.

Notice that this depends on the stock transaction created by exercise - not on whether you originally bought or sold the option.

Let’s walk through an example:

An investor goes long 1 BCD Apr 25 call at $3. BCD’s market price rises to $30, and the investor exercises the option. What is the tax consequence?

Exercising a long call means the investor buys 100 shares at the strike price ($25). Because the investor is buying stock, they establish cost basis.

Start with the strike price ($25 per share), then adjust for the option premium:

  • The investor paid the premium to buy the call, so the premium is added to cost basis.

Cost basis per share = $25 + $3 = $28.

A quick way to double-check is to use breakeven. For exercise questions, the cost basis (or sales proceeds) will equal the option’s breakeven. For a call, breakeven is strike price + premium: $25 + $3 = $28.

Sidenote
Holding periods after exercise

When a long stock position is established through a long call or short put exercise, the stock’s holding period begins counting the day after the exercise.


Let’s see if you can make it through three more examples on your own:

A CDE Sep 75 call is written for $6 when CDE’s market price is $74. CDE’s stock price rises to $79, and the option is assigned. What is the tax consequence for the writer?

(spoiler)

Answer = $81 sales proceeds (per share)

When a written (short) call is assigned, the writer must sell 100 shares at the strike price ($75). Because the writer is selling stock, they establish sales proceeds.

Start with the strike price ($75 per share), then adjust for the option premium:

  • The writer received the premium, so the premium is added to sales proceeds.

Sales proceeds per share = $75 + $6 = $81 (or $8,100 total).


Let’s look at some put contract examples:

An investor goes long 100 shares of PEP stock at $120. A few months later, they go long 1 PEP Feb 120 put at $9 when PEP’s market price is $115. A few weeks later, PEP’s market price falls to $105, and the investor exercises the option. What is the tax consequence for both the stock and option?

(spoiler)

Answers:

  • Stock = $120 cost basis (per share)
  • Option = $111 sales proceeds (per share)
  • Overall = $9 capital loss

This question includes both the original stock purchase and the option exercise.

1) Stock cost basis The investor bought PEP at $120, so the stock’s cost basis is $120 per share.

2) Sales proceeds created by exercising the put Exercising a long put means the investor sells the shares at the strike price ($120). Because the investor is selling stock, they establish sales proceeds.

Start with the strike price ($120 per share), then adjust for the option premium:

  • The investor paid the premium to buy the put, so the premium is subtracted from sales proceeds.

Sales proceeds per share = $120 − $9 = $111.

3) Overall tax consequence Compare cost basis to sales proceeds:

  • Cost basis: $120
  • Sales proceeds: $111

That’s a $9 capital loss per share, or $900 total.


One last example involving put contracts:

An investor writes 1 CBA Jun 150 put at $12 when CBA’s market price is $145. CBA’s market price falls slightly to $143, and the option is assigned. What is the tax consequence?

(spoiler)

Answer = $138 cost basis (per share)

When a written (short) put is assigned, the writer must buy 100 shares at the strike price ($150). Because the investor is buying stock, they establish cost basis.

Start with the strike price ($150 per share), then adjust for the option premium:

  • The writer received the premium, so the premium is subtracted from cost basis.

Cost basis per share = $150 − $12 = $138 (or $13,800 total).


This video summarizes the option taxation concepts we’ve discussed in this chapter:

Option expiration tax consequence

  • Capital gain or loss equal to the premium

Option trading tax consequence

  • Capital gain or loss equal to the overall gain or loss

Option exercise tax consequence

  • Establishes cost basis if shares purchased
  • Establishes sales proceeds if shares are sold
  • Premium must also be factored

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Basic rules

You learned several options strategies in the strategies unit. This chapter focuses on the basic tax consequences of options.

The topics here assume you already know how options work. If you need a refresher on strategies, use the link above.

We’ll cover tax consequences related to:

  • Expiration
  • Trading
  • Exercise

Expiration

When an investor buys or sells an option, there are three potential outcomes:

  • Expiration
  • Trading the contract (closing out)
  • Exercise

Here, we’ll focus on expiration.

When an options contract expires, the tax result is a capital gain or loss equal to the premium. In other words, the entire premium is recognized as a gain or loss at expiration.

An investor goes long 1 ABC Jan 50 call at $4 when ABC’s market price is $51. Several months later, the ABC’s market price falls to $49 and stays there until expiration. What is the tax consequence?

Can you figure it out?

(spoiler)

Answer = $400 capital loss

The investor bought a call, and it expires out of the money (no intrinsic value). Calls expire if the market price is below the strike price at expiration.

The investor paid $4 per share ($400 total) and the option expires worthless, so they realize a $400 capital loss.

Let’s try another example:

One August 80 put is written for a premium of $7 when the underlying stock’s market price is $78. Just prior to expiration, the stock’s market price rises to $90. What is the tax consequence?

(spoiler)

Answer = $700 capital gain

The investor wrote (sold) a put, and it expires out of the money (no intrinsic value). Puts expire if the stock’s market price is above the strike price at expiration.

The investor received $7 per share ($700 total) and the option expires unexercised, so they realize a $700 capital gain.

Sidenote
Timing of tax reporting

A capital gain or loss related to an option expiration is reported to the Internal Revenue Service (IRS) in the year the option expires.

For example, suppose an investor goes short an option and receives a premium in December 2025, and the option expires in July 2026. Even though the premium was received in 2025, the premium income is reported on the investor’s 2026 tax return.

Trading

Before an option is exercised or expires, an investor can trade out (close out) of the position. This concept was covered in the issuance & the market chapter.

From a tax perspective, closing out creates a capital gain or loss equal to the contract’s overall gain or loss (what you paid versus what you received when you closed).

An investor goes long 1 XYZ Dec 35 put at $5 when XYZ’s market price is $36. XYZ’s market price falls to $32, and the investor closes the contract at intrinsic value. What is the tax consequence?

(spoiler)

Answer = $200 capital loss

To find the gain or loss, compare:

  • The premium paid to open the position, and
  • The premium received when the position is closed.

The put cost $5 per share ($500 total). When the stock falls to $32, the put is in the money by $3, so the investor closes the position by selling the option for $3 per share ($300 total).

Buying for $500 and later selling for $300 results in a $200 capital loss.

One more example:

A client of yours writes 1 ZZZ Sep 60 call for a premium of $4. A few months later, the investor closes the position at $3. What is the tax consequence?

(spoiler)

Answer = $100 capital gain

The client initially wrote (sold) the call for $4 per share ($400 total). To close a short option position, the client must buy it back. They close by purchasing the option for $3 per share ($300 total).

Selling for $400 and later buying back for $300 results in a $100 capital gain.

Exercise

Taxes related to exercising options are more complicated than expiration or trading.

Instead of creating an immediate capital gain or loss on the option itself, an exercise adjusts the tax numbers on the underlying security (usually stock). Specifically, exercise establishes either:

  • Cost basis (the total cost to buy the shares), or
  • Sales proceeds (the total amount received when the shares are sold).

Which one you establish depends on what happens to the stock at exercise:

  • If the exercise results in buying shares, you establish cost basis.
  • If the exercise results in selling shares, you establish sales proceeds.

Notice that this depends on the stock transaction created by exercise - not on whether you originally bought or sold the option.

Let’s walk through an example:

An investor goes long 1 BCD Apr 25 call at $3. BCD’s market price rises to $30, and the investor exercises the option. What is the tax consequence?

Exercising a long call means the investor buys 100 shares at the strike price ($25). Because the investor is buying stock, they establish cost basis.

Start with the strike price ($25 per share), then adjust for the option premium:

  • The investor paid the premium to buy the call, so the premium is added to cost basis.

Cost basis per share = $25 + $3 = $28.

A quick way to double-check is to use breakeven. For exercise questions, the cost basis (or sales proceeds) will equal the option’s breakeven. For a call, breakeven is strike price + premium: $25 + $3 = $28.

Sidenote
Holding periods after exercise

When a long stock position is established through a long call or short put exercise, the stock’s holding period begins counting the day after the exercise.


Let’s see if you can make it through three more examples on your own:

A CDE Sep 75 call is written for $6 when CDE’s market price is $74. CDE’s stock price rises to $79, and the option is assigned. What is the tax consequence for the writer?

(spoiler)

Answer = $81 sales proceeds (per share)

When a written (short) call is assigned, the writer must sell 100 shares at the strike price ($75). Because the writer is selling stock, they establish sales proceeds.

Start with the strike price ($75 per share), then adjust for the option premium:

  • The writer received the premium, so the premium is added to sales proceeds.

Sales proceeds per share = $75 + $6 = $81 (or $8,100 total).


Let’s look at some put contract examples:

An investor goes long 100 shares of PEP stock at $120. A few months later, they go long 1 PEP Feb 120 put at $9 when PEP’s market price is $115. A few weeks later, PEP’s market price falls to $105, and the investor exercises the option. What is the tax consequence for both the stock and option?

(spoiler)

Answers:

  • Stock = $120 cost basis (per share)
  • Option = $111 sales proceeds (per share)
  • Overall = $9 capital loss

This question includes both the original stock purchase and the option exercise.

1) Stock cost basis The investor bought PEP at $120, so the stock’s cost basis is $120 per share.

2) Sales proceeds created by exercising the put Exercising a long put means the investor sells the shares at the strike price ($120). Because the investor is selling stock, they establish sales proceeds.

Start with the strike price ($120 per share), then adjust for the option premium:

  • The investor paid the premium to buy the put, so the premium is subtracted from sales proceeds.

Sales proceeds per share = $120 − $9 = $111.

3) Overall tax consequence Compare cost basis to sales proceeds:

  • Cost basis: $120
  • Sales proceeds: $111

That’s a $9 capital loss per share, or $900 total.


One last example involving put contracts:

An investor writes 1 CBA Jun 150 put at $12 when CBA’s market price is $145. CBA’s market price falls slightly to $143, and the option is assigned. What is the tax consequence?

(spoiler)

Answer = $138 cost basis (per share)

When a written (short) put is assigned, the writer must buy 100 shares at the strike price ($150). Because the investor is buying stock, they establish cost basis.

Start with the strike price ($150 per share), then adjust for the option premium:

  • The writer received the premium, so the premium is subtracted from cost basis.

Cost basis per share = $150 − $12 = $138 (or $13,800 total).


This video summarizes the option taxation concepts we’ve discussed in this chapter:

Key points

Option expiration tax consequence

  • Capital gain or loss equal to the premium

Option trading tax consequence

  • Capital gain or loss equal to the overall gain or loss

Option exercise tax consequence

  • Establishes cost basis if shares purchased
  • Establishes sales proceeds if shares are sold
  • Premium must also be factored