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[Note: I originally posted this on the "SA Ask the Stock Advisor Team" board, but no one knew there and advised mer to post here!]

Not that this case is true for me this year (and probably not for several), but what is the appropriate way to handle taxes when you have large long-term cap gains? IOW, if you cashed out of a position in July for what amounts to, say half, your day job withholding earnings for the year, do you immediately pay the IRS 15%? How do you avoid penalties come April 15?

I'm sure this has been asked and answered several times before, but I couldn't discover any links, at least through my search efforts.

Thanks for any insight,

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