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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?

There are various safe harbors explained in IRS Publication 505. The simplest, especially when you have an income spike, is to make sure that 2008 withholding is at least as much as 2007 tax (110% of 2007 tax if 2007 AGI was over $150,000). If you do that you won't have a penalty regardless of how much you owe April 15.

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