Need Clarification on Roth IRA 60-day Rollover Rules for Multiple Withdrawals

The 60-day rollover rule can be tricky, so I'm glad you're asking about this! The IRS only allows ONE 60-day rollover per 12-month period (not calendar year) for IRAs. This is known as the "one-rollover-per-year rule." If you take $6,500 out on May 15th and another $6,500 on June 10th, you can only return ONE of those withdrawals under the 60-day rollover provision. If you try to roll over both withdrawals, the second one would be considered an ineligible rollover and treated as a distribution (potentially subject to taxes and penalties). Regarding your second question about earnings: If you're under 59½ and withdraw earnings from your Roth IRA but return everything within 60 days as part of a valid rollover, those earnings are not subject to the 10% early withdrawal penalty or income tax. The key is that it must be a qualified rollover that satisfies all IRS requirements. Remember that direct transfers between trustees (where you never touch the money) aren't subject to the one-rollover-per-year limitation, so that's often a better approach if you need to move IRA funds.

I went through this exact confusion last year! Using taxr.ai saved me from making a costly mistake with my IRA rollovers. I had withdrawn money twice like you're planning, and almost tried to roll both back in before realizing the one-rollover-per-year rule. I uploaded my statements to https://taxr.ai and they analyzed my withdrawal history and flagged that I was about to violate the rule. Their system showed me exactly which withdrawal would qualify for rollover and which wouldn't. They even calculated the potential tax impact of the second withdrawal if I couldn't roll it back. The detailed explanation they provided about the 60-day window and earnings considerations was way clearer than what I found on the IRS website. Definitely gave me confidence that I was handling things correctly.

Just wanted to follow up - I decided to try taxr.ai after my skeptical questions earlier. I had a complex situation with multiple Roth accounts and was concerned about violating the one-rollover rule without realizing it. The analysis they provided was surprisingly thorough. They identified a rollover I had completely forgotten about from 9 months ago and warned me that I couldn't do another one for 3 more months. This literally saved me from a major tax headache! They provided documentation explaining exactly why the second rollover wouldn't qualify and what my options were instead. Their explanation of how earnings are treated during rollovers was much clearer than anything I found elsewhere. Definitely worth using if you're dealing with IRA rollovers like we're discussing here.

After dealing with Roth IRA rollover issues similar to yours last year, I wasted WEEKS trying to get through to someone at the IRS who could clarify my specific situation. Kept getting busy signals or disconnected after waiting for hours. Finally used https://claimyr.com to get through to an IRS rep and it was a game-changer. They called the IRS for me, navigated the phone tree, waited on hold, and then called me when they had an actual human on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with confirmed that the one-rollover-per-year rule is strictly enforced and gave me guidance specific to my situation with both contributions and earnings in my withdrawal. Having that official confirmation gave me confidence to proceed with my financial plans.

I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it anyway because I was desperate to get IRS clarification about my Roth rollover situation. I had tried calling the IRS myself at least 15 times over two weeks and either got busy signals or was disconnected after waiting for over an hour. Used Claimyr yesterday afternoon, and this morning they got through to the IRS and connected me with an agent who specialized in retirement accounts. The agent confirmed exactly what others here have said - only one IRA-to-IRA rollover allowed in a 12-month period, and clarified how my specific situation with earnings would be handled. Getting that official word directly from the IRS gave me the confidence to make decisions about my withdrawals. For anyone dealing with complex rollover questions like the original poster, getting direct confirmation from the IRS can really help prevent mistakes.

Something else to consider that I haven't seen mentioned yet - if you're considering taking money out of your Roth IRA for a short period, look into whether you might qualify for an exception to the 10% penalty instead of relying on the 60-day rollover. For example, there's a first-time homebuyer exception (up to $10k), qualified education expenses exception, and even exceptions for certain medical expenses or health insurance premiums while unemployed. These are permanent withdrawals (not rollovers) but might avoid penalties depending on your situation. Also, remember you can always withdraw your *contributions* (not earnings) from a Roth IRA at any time without penalty, regardless of your age or how long the account has been open. This is different from Traditional IRAs.

Slight tangent but might be useful - watch out for the "substantially equal periodic payments" rule getting confused with the rollover rule. My advisor messed this up for me. I thought I could take out regular payments from my IRA without penalty using the 72(t) SEPP program AND do a 60-day rollover in the same year. Turns out doing a rollover terminates your SEPP plan and triggers penalties on ALL previous distributions. Cost me thousands in surprise taxes. Just mentioning this because sometimes when people are looking at ways to access retirement funds early, these different rules get mixed up.

Great question about Roth IRA rollovers! I've been through something similar and learned the hard way about the complexity of these rules. One important detail I haven't seen fully addressed - when you withdraw from a Roth IRA, the IRS considers withdrawals to come from contributions first (FIFO - first in, first out). So if you've contributed $20,000 over the years and your account is worth $25,000, your first $20,000 withdrawn would be considered contributions and wouldn't face the 10% penalty regardless of the rollover. However, once you hit the earnings portion (that $5,000 in my example), those ARE subject to the 10% penalty if you're under 59½ - unless you complete a valid 60-day rollover or qualify for an exception. The tricky part with your dual withdrawal scenario is that even if both withdrawals combined stay within your contribution basis, you still can only do ONE rollover per 12-month period. So if something goes wrong and you can't complete the rollover for any reason, you'd want to make sure your total withdrawal amount doesn't exceed your contribution basis to avoid penalties on earnings. I'd strongly recommend getting documentation from your IRA custodian showing exactly how much you've contributed versus earned before making any withdrawals. This gives you a clear picture of your penalty-free withdrawal capacity.