Retirement tax questions

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There are indeed some situations where Roth IRA withdrawals are taxable, but if we are talking specifically about contributions (and not earnings or conversions), withdrawal of contributions is non-taxable.   However, you do need orderly records of your past contributions and withdrawals because, if audited, you would have to prove that you only withdrew contributions.  But, be careful because other Roth accounts (like a Roth-option 401k) may have different rules, and some people don't realize there is a difference between Roth IRAs and other accounts like Roth 401ks.