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Take a look at Form 8606 available from the irs.gov website. It will answer most of your questions (for an IRA).

A portion of any distribution from the account is taken as a return of your after tax contribution. A portion is taxable income.

The form is filed every year and keeps track of the after tax portion of your IRA, so the taxable component can be recalculated each year you take a distribution.
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