Tax Loss Harvesting and ESPP / RSUs

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Topic Author
rubberbandman
Posts: 2
Joined: Sat May 28, 2022 10:58 am

Tax Loss Harvesting and ESPP / RSUs

Post by rubberbandman »

Hello All,

I have access to an ESPP and am also awarded RSUs through my employer. I have decided to hold a small portion of my portfolio in shares of my company's stock.
  • I currently have some ESPP shares that are at a loss (held < 1 year)
  • It has been more than 30 days since I received my most recent shares
  • It will be more than 30 days until I receive my next shares
  • Share price is currently below my previous purchase price but above my future purchase price
Is it possible to tax loss harvest some of my ESPP shares? I will continue to receive more shares than I intend to hold in the future, so I will be selling some future shares when received. If I sell these shares for a loss, I would sell fewer shares from the next batch to keep my target number. From what I can tell it meets the rules for tax loss harvesting. However, since I have future shares guaranteed by share price or quantity, I would not be missing out on any gains during the 30 days I would be "not be invested in these shares". It seems like this is a potential loophole in the TLH laws, so I want to double check that I'm not missing anything.
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