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Tax Loss Harvesting - Sanity check


changegonnacome
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Its that time of year - i wanted to sanity check a couple of maneuvers/scenarios with folks here to make sure I'm not triggering a wash sale, constructive sale or any other IRS troubles.

 

 - Scenario One - 

Step 1 - Sell XYZ stock for $65, cost basis of $85 for long term capital loss

Step 2 - Sell an OTM 1 year put option.....$55 strike

Step 3 - Buy back XYZ after 31 Days

 

From what I can gather its all good if sold put is OTM......any 15% banding rules here? Could I fly closer to $65 current price and just ensure the put excercise date is outside the 31 days?

 

-Scenario Two-

Short Position (temporarily hopefully) gone wrong......but with juicy short term capital losses to use up

 

Step one - Buy to cover XYZ stock at $100, cost basis was $50....good short term losses

Step Two - Sell Calls on XYZ stock with $125 strike (does call expiration even matter here??)

Step Three - After 34 days (31 days + 3 day time taken to deliver shares to broker) sell short XYZ stock again to recreate orginal short position

 

Any thoughts on Scenario Two above?

 

Also posting some links I've found in other threads & web broadly that have proven useful lest anyone else is playing around with tax loss harvesting options right now:

https://www.nysscpa.org/news/publications/the-trusted-professional/article/tools-techniques-to-shield-and-defer-taxes-on-unrealized-stock-gains 

 

Strategies to Help Clients Around the Wash Sale Rule | Nasdaq
https://www.optionstaxguy.com/substantially-identical

https://www.optionstaxguy.com/wash-sales

 

Wash Sales and Options – Fairmark.com
 

 

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