Confused about Indirect Roth IRA to Roth Rollover - Dates Don't Line Up?

The 60-day rollover rule is what applies in your situation. When you take a distribution from a Roth IRA that you intend to roll over, the IRS gives you 60 days from the date you receive the distribution to complete the rollover to another Roth IRA. What's interesting in your case is that you actually funded the new Roth IRA before receiving the distribution from the old one. This is sometimes called "floating" the rollover, and it doesn't automatically disqualify your rollover. The key question is whether both transactions occurred within the 60-day window. Since you were only moving original contributions and not earnings, you have additional flexibility. Original contributions to Roth IRAs can be withdrawn at any time without tax or penalty. However, the way you describe the transaction suggests you intended it as a rollover rather than a withdrawal followed by a new contribution. I would recommend gathering documentation showing both transactions - the withdrawal from Vanguard and the deposit to Fidelity - to demonstrate they occurred within the 60-day period. This would support treating it as a valid rollover even if the timing wasn't perfect.

After dealing with a similar indirect rollover nightmare last year, I found taxr.ai (https://taxr.ai) incredibly helpful for sorting through my documentation. It saved me hours of digging through statements and tracking down the exact timeline of events. I uploaded my Vanguard distribution notice and Fidelity contribution confirmation, and it helped me identify that my rollover was valid even though I had a weird timing situation like yours. Their analysis showed that the IRS considers the full timeline rather than just matching transaction dates, which was a huge relief. The tool also helped me document everything properly in case of questions later. Definitely worth trying if you're worried about timing issues with your rollover.

Just wanted to follow up - I tried taxr.ai after seeing this thread and it was genuinely helpful for my complicated rollover situation. I was hesitant at first (as you could tell from my earlier comment), but after uploading my statements from three different institutions, it clearly identified where my tax software was getting things wrong. The analysis showed that my rollovers were all valid despite some weird timing issues, and it helped me correct my tax forms before filing. It even created a detailed explanation document I could use if I ever got audited. I was particularly impressed that it caught some basis calculation errors that would have resulted in double taxation of part of my retirement savings.

If you're still trying to get clarification from the IRS directly, good luck with that... I spent WEEKS trying to get through to someone who could answer my Roth conversion questions last year. After 30+ attempts and hours on hold, I finally discovered Claimyr (https://claimyr.com) which got me connected to an actual IRS agent in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with confirmed that what matters for indirect rollovers is the 60-day window, not whether the exact same dollars moved between accounts. They also explained that since you were only moving original contributions, you have even more flexibility. Definitely worth getting that official confirmation rather than stressing about whether you're doing it right.

I need to eat my words from my skeptical comment above. After another morning of failed attempts to reach the IRS about my own rollover issue, I broke down and tried Claimyr. Within 35 minutes, I was talking to an actual IRS representative who answered all my questions about my botched rollover timing. The agent confirmed that as long as I completed the entire process within 60 days, the fact that I "floated" the money (using different funds temporarily) doesn't matter. She also explained that there's a specific way to report this on my taxes to avoid confusion and unnecessary penalties. Would have taken me weeks to get this information otherwise, if ever. For anyone dealing with timing issues on rollovers, getting direct confirmation from the IRS saved me a lot of anxiety and potentially hundreds in unnecessary taxes.

Quick tip for anyone in this situation: request a waiver of the 60-day rollover requirement if you're outside the window! IRS Publication 590-A has details on this. My rollover was delayed because my first financial institution sent a paper check to my old address, and I was able to get relief through a self-certification procedure. For the original poster - if your transactions were within 60 days of each other, you're fine. The fact that you pre-funded the new account before receiving the distribution doesn't invalidate the rollover as long as the total amounts match up and everything happened within the 60-day window.

Anyone know if the same 60-day rule applies when moving from a 401k to a Roth IRA? My company's being acquired and I need to figure out what to do with my retirement account ASAP.

I went through a very similar situation last year with my Roth IRA rollover between Schwab and TD Ameritrade. The timing was off by about a week, and I was panicking about the tax implications. After consulting with a tax professional, I learned that what you've described should qualify as a valid rollover. The key factors working in your favor are: 1) You're only moving original contributions, not earnings, 2) Both transactions occurred within the 60-day window, and 3) The amounts match up. The IRS doesn't require the exact same physical dollars to move - they recognize that money is fungible. What matters is the timing and amounts. Since you initiated the process properly and completed it within 60 days, you should be able to report this as a rollover rather than a distribution. However, you'll want to be very careful with your tax reporting. Make sure you have documentation showing both the distribution date from Vanguard and the contribution date to Fidelity. If there's any question during tax review, having a clear paper trail will support your position that this was an intended rollover, not separate transactions. Given that you've already filed, you might want to wait and see if you receive any notices from the IRS before filing an amended return. Sometimes these situations resolve themselves without additional action needed.