Taxes and Options

If you let an option expire you obviously take a capital loss, but what about if you buy an option on the exact same stock with in the 30 day does that count as a back wash rule?

Like one expires in June --- took loss other expires in july but bought it

HALPSZ

7 Comments
 

If you're worried, I remembered reading up on wash sale rules and options capital gains treatment in West Federal Taxation a few years ago. They come out with a book every year, but 2005 is too long ago for me to remember the exact details.

If this is a problem that a major institution is facing and you're prepared to pay thousands of dollars to see if there's a way to save you a few million in tax, I can hook you up with a nationally recognized expert on derivatives taxation. Year-end is kinda busy for tax accountants, though.

 
Best Response

Yes, Eddie, but if you exercise that option, all sorts of craziness ensues when it comes to holding periods and wash sales, IIRC.

Also, methinks the IRS would frown on replacing a stock holding with a virtual long position on options to avoid wash sale rules. I think that qualifies as a substantially equivalent security or whatever the wording is.

That's why you really want to ask a CPA for an answer on this stuff. Wash sales suck, particularly if you have a wash sale in a taxable account and buy the replacement in an IRA. That really sucks, since you lose your basis permanently.

Oh well, apparently, you win kudos for reading the question the most carefully and making all the logical deductions that would be appropriate before answering.

 

It's really just standard wash sale stuff. If you exercise an option and purchase the stock, and then sell the stock for a loss somewhere down the line, you're just not allowed to buy the stock back in the next 30 days without nullifying your taxable event. The option doesn't play a part in the wash sale.

I think the OP was concerned about being unable to write off the total loss on the expired option if he buys another option on the same stock within 30 days. The answer to that is no, it's not a problem, you still get tax credit for the loss as the new option is considered an entirely different security.

 

Dicta non qui enim architecto omnis perspiciatis tempora eius. Ipsam occaecati corporis voluptatem qui. Veniam sunt optio voluptatibus.

Unde non dolorum earum et quia et pariatur. Sapiente odio molestiae alias fugiat. Ducimus odio molestiae deserunt. Ratione qui ducimus vel fugiat ratione vel eaque. Excepturi quasi enim et sit.

Et occaecati qui qui similique nihil. Nihil sunt cum est expedita distinctio doloremque similique. Nostrum cumque repellat impedit et perspiciatis.

Career Advancement Opportunities

October 2026 Investment Banking

  • Evercore 01 99.5%
  • Moelis & Company 01 98.9%
  • JPMorgan 01 98.4%
  • Guggenheim Partners 02 97.9%
  • Morgan Stanley 06 97.4%

Overall Employee Satisfaction

September 2026 Investment Banking

  • Moelis & Company No 99.5%
  • Morgan Stanley 02 98.9%
  • Evercore 01 98.4%
  • Banco Santander 02 97.9%
  • BMO Capital Markets 12 97.4%

Professional Growth Opportunities

October 2026 Investment Banking

  • Evercore 01 99.5%
  • Moelis & Company 01 98.9%
  • Morgan Stanley 05 98.4%
  • Goldman Sachs 01 97.9%
  • JPMorgan No 97.4%

Total Avg Compensation

October 2026 Investment Banking

  • Vice President (16) $429
  • Associates (56) $261
  • 3rd+ Year Analyst (8) $210
  • 2nd Year Analyst (28) $184
  • Intern/Summer Associate (16) $161
  • 1st Year Analyst (84) $151
  • Intern/Summer Analyst (76) $101
notes
16 IB Interviews Notes

“... there’s no excuse to not take advantage of the resources out there available to you. Best value for your $ are the...”

Leaderboard

1
redever's picture
redever
99.2
2
BankonBanking's picture
BankonBanking
99.0
3
Secyh62's picture
Secyh62
99.0
4
kanon's picture
kanon
99.0
5
Betsy Massar's picture
Betsy Massar
98.9
6
CompBanker's picture
CompBanker
98.9
7
GameTheory's picture
GameTheory
98.9
8
DrApeman's picture
DrApeman
98.9
9
dosk17's picture
dosk17
98.9
10
Jamoldo's picture
Jamoldo
98.8
success
From 10 rejections to 1 dream investment banking internship

“... I believe it was the single biggest reason why I ended up with an offer...”