This is a question ONLY about applicability of the whitewash rule, not about option trading strategies.
I sold ROKU option puts at $260, they are assigned today, the now price is $238.
That means on Monday I bought 1000 shares of Roku at $260, while the market price is $238. If I sell them immediately I will book for tax purpose a short cap loss of $22,000. If I want to buy ROKU back at less than $260 I will need to wait 30+ day,
or the whitewash rule triggers.

An alternative scenario I am thinking is to still sell now ROKU for the loss of $22,000 and also sell an option put with strike close to $238 and expiration longer than 30 days. That means, I collect now the premium from selling the put, and after 30+
days, ROKU is still at or below $238 I will buy back (assigned) the 1000 ROKU shares. Will this strategy trigger a whitewash rule?

Appreciate the help, Alex

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