Roth IRA withdrawal guidelines. Generally, early distributions from a retirement account are income and you must report it on your return.As for withdrawals, note that contributions can be withdrawn at any time. When Can I Withdraw Roth 401(k) Funds? In general, you can begin withdrawing Roth 401(k) earnings when you are 59½ years old. Please enter a specified term for a period not greater than your life expectancy. The Roth IRA fiveyear rule says you can withdraw your investment earnings taxfree and penaltyfree as long as you've held the account for at least five years. Tax-free and penalty-free withdrawals also can be taken under circumstances other than first-home purchases, such as the owner's death. If there are multiple Beneficiaries, each Beneficiary must complete a form. Qualified Roth IRA distributions are not subject to state and local taxation in most states.