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Except for the possibility of having a wash sale in a taxable account for shares held in a retirement plan (or vice versa) , there is no other interaction of the accounts.
That is, the gain or loss from the one type of account does not affect the holding period of the same stock held in the other type of account.
Neither does selling short in nonretirement accounts change the holding period of stock that you already own prior to the short sale (presuming that you are not using those shares to satisfy the short sale but buying other shares or trading the option.)
You will want to keep any stock transferred from the retirement plan in an account that is separate from your other holdings to easily be able to identify the holding period from a given sale of the stock.
Please ask if you need more discussion or clarification.
That sounds smooth when you say it fast! Can you provide a reference to the regs.
I have seen enough to know that there are areas of tax risk if not implemented properly, especially if selling short for shares one already owns. Understand also, that after I do the NUA distribution, the NUA shares and the PUTs would be in the same account; this raises the question of whether it matters if the PUTs are acquired before or after the NUA distribution.
Not sure what more you need.
I will opt out so another expert can help.
Here is what I think I know:
If you exercise a put option and sell the underlying securities, the premium you paid for the option (plus commissions and fees) reduces the amount you realize on the sale of the underlying securities. Determining whether you have a short-term or a long-term gain or loss depends on when you purchase the underlying securities in relation to when you bought the put. If you sell securities that you had held long term at the time you bought the put, you will have a long-term gain or loss.
If you sell securities you had held short term at the time you bought the put, or if you purchased the securities after you bought the put (but before you exercised the put), the transaction will be treated as a short sale. That is, your holding period for the securities starts on the date you exercise the option, regardless of when you actually bought them.
If the put is a married put, the gain or loss will be short-term or long-term, depending on how long you had held the securities before you exercised the put.
I 'm looking for something to clarify how NUA assets are handled with regard to date of acquisition. While I've been holding the assets in a 401k plan for a very long time, I am distributing them out as NUA in the near future so one might say they I've "held" them short term, or that I acquired them after the PUT was purchased.
I do understand everything you said about NUA.
I'm concerned about:
If you sell securities you had held short term at the time you bought the put, or if you purchased the securities after you bought the put (but before you exercised the put), the transaction will be treated as a short sale.
I'm trying to determine if hedging NUA is covered in the regs anywhere to eliminate the possibility that "holding period" associated with hedging does not inadvertently pull NUA into short sale. I understand the NUA part; but I'm not so sure one can extrapolate basic NUA principles to the implication of hedging NUA.
Your concept of NUA being tax-law based rather than holding period base may be the string I need to pull to tie thse concepts together. I'm going to accept this as an answer.