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IOW, is a short put expiring >30days after the losing sale of its underlying which does not get exercised within 30days considered to be a substantially identical security?

'- Revenue Ruling 85-87 states that a short put option can sometimes be
considered "an option to acquire" its underlier if it is virtually certain that the option will be
exercised. '

so if it is "viritually certain" then you're subject to the wash sale rule.
They probably don't define "virtually certain" - but you can look up the ruling and see if that clears things up - that and pub 550.

Personally I'd avoid that type of scenario where it's at best an unknown. It sounds like you're looking to play cute with the IRS and IMO that'll probably come back to bite you.
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