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Dear Peter,

This issue has me really angry. The IRS and the Congress, in my opinion, have a big debt with us, option traders, in defining when and how the rules for wash sale apply so we can pay our taxes with certainty.
After reading a lot of rules, laws and publications, in particular, the best ones in my opinion:
http://www.tradelogsoftware.com/resources/wash-sales/
https://fairmark.com/investment-taxation/capital-gain/
Besides the basic case (stock-stock), my conclusion is that long CALLs are always considered substantially equivalent to stock; and PUTs, only if they are DITM, if they are ITM you are on thin ice, so it may be better to be safe than audited. And that rolling short positions always trigger a wash sale, even in the super weird case that you close a short call and then buy stock.
My initial disagreements are logical but wrong, the law is the law and we have to follow.
The worst part of all this investigation is that after so many years, there are no clear rules about what to do or how in many cases and that each CPA may have a different opinion and you have to risk getting an audit and not being able to defend yourself against the auditor OPINION.

Thanks to AJ too for shedding light to this issue.

-
Juan
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