Those are both great questions.
If you have funds in a ROTH IRA, are over 59 1/2 and have allowed all funds to sit there for more than 5 years, none of the earnings would be subject to income tax, as well as the fact, you can always withdraw your own investment within the ROTH IRA because after-taxed funds were used to invest in the ROTH IRA in the first place.
If you take funds out of a ROLLOVER IRA, they are subject to income tax at year-end and it would be the policy of the plan administrator to allow you to withhold any tax at all on the day of distribution, but they would need to you to sign a form holding them harmless, if you choose to do so.
No matter what, income tax could still be due on your tax return and may submit you to underpayment penalties by not making estimated tax payments at the time the income was withhdrawn during that tax quarter.
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