Roth IRA withdrawal guidelines. Roth IRA withdrawal rules: When are withdrawals tax free?If not met, Traditional and Roth IRA funds may be subject to the IRS early withdraw penalty of 10 percent. The fiveyear rule requires you to satisfy a fiveyear holding period before you can withdraw Roth IRA earnings taxfree or converted principal penaltyfree. You must wait five years to take tax-free withdrawals, even if you're already age 59½ or older. How to Do a Roth IRA Conversion. Complete Form W-4R to have payers withhold the correct amount of federal income tax from your nonperiodic payment or eligible rollover distribution from an. With a Roth IRA, you can always withdraw your contributions without tax or penalty before you turn 59½ since you've already paid tax on them. You're always eligible for tax and penaltyfree withdrawals on contributions, but you must meet certain Roth IRA rules for withdrawal to withdraw earnings. Attach a completed Citibank IRA and Roth IRA Withdrawal and Tax Withholding Election Form.