Roth IRA withdrawal guidelines. Does your current financial situation make a cash withdrawal necessary?People over age 59½ who've held their accounts for at least five years can withdraw contributions and earnings with no tax or penalty. Roth IRA withdrawal rules: When are withdrawals tax free? In lieu of a refund you may freeze your account and apply for a monthly benefit as early as 180 days prior to your 60th birthday. To determine whether or not the AMT applies, taxpayers must fill out IRS Form 6251. IRAs are not taxable when. "rolled over," unless "rolled over" into a Roth IRA. Generally, funds held in traditional IRAs are only taxed once withdrawn.