What is the deadline for reporting my early Roth IRA withdrawal from 2023?

For your early Roth IRA withdrawal, you'll need to use the actual distribution date - that's the date the money was officially distributed from your IRA, which should be on the 1099-R form you received from your financial institution. It's not the date you requested it or when it hit your bank account. Since you're under 59½, you're generally subject to a 10% early withdrawal penalty on any earnings withdrawn (not your contributions), unless you qualify for an exception. Common exceptions include first-time home purchases, certain education expenses, or unreimbursed medical expenses exceeding a certain percentage of your AGI. Remember though, with Roth IRAs, you can always withdraw your original contributions tax and penalty-free at any time. It's only the earnings portion that might be taxable and subject to penalties if taken out early.

I had a similar issue with figuring out dates for an early withdrawal. I was totally confused about which forms to use and what dates to put where. I ended up trying this tool called taxr.ai (https://taxr.ai) and it saved me so much headache. You can upload your 1099-R and it breaks everything down - shows you exactly which dates to use, calculates if you owe the 10% penalty, and even helps determine if you qualify for any exceptions. The whole confusion about contributions vs earnings that you mentioned was giving me anxiety too, but their system actually explains all of this in normal human language instead of IRS-speak. It identified that part of my withdrawal was actually contributions I could take out penalty-free.

Just wanted to follow up about using taxr.ai that someone mentioned above. I was skeptical but decided to try it since my withdrawal situation was complicated (had both Roth and traditional IRAs plus a rollover from an old 401k). It was actually really helpful! Uploaded my forms and it immediately identified which portions of my withdrawal were contributions vs. earnings. Turns out I qualified for the first-time homebuyer exception which saved me from the 10% penalty on part of my withdrawal. The tool even created a detailed report explaining exactly what to enter on each tax form line, which dates to use, and why. Honestly wish I'd known about this sooner - would have saved me hours of stress trying to interpret IRS publications.

For anyone dealing with the IRS about early withdrawals or penalties, just want to share something that helped me. After waiting on hold with the IRS for literally 4+ hours last month trying to get clarification on my withdrawal situation, I found this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in under 20 minutes. They have this system that navigates the IRS phone tree and holds your place in line, then calls you when an agent is about to pick up. Saved me so much time! You can see how it works here: https://youtu.be/_kiP6q8DX5c I had questions about whether my Roth withdrawal qualified for a hardship exemption, and being able to actually talk to someone at the IRS directly made all the difference rather than guessing.

I owe everyone an apology about my skeptical comment above about Claimyr. I ended up trying it because I was desperate to resolve an issue with my own Roth IRA distribution that had been misreported by my bank. I honestly can't believe it worked. After multiple failed attempts spending hours on hold, Claimyr got me through to an IRS agent in about 15 minutes. The agent was able to confirm exactly which date I needed to use (the distribution date on my 1099-R) and explained how to document that the bank had made a reporting error. The way it works is exactly as described - they handle the hold time, then call you when an agent is available. Was absolutely worth it for getting a definitive answer directly from the IRS rather than stressing about whether I was doing it right.

For your Roth IRA withdrawal, don't forget to check if you qualify for any exceptions to the 10% penalty! I thought I was stuck paying it until my accountant pointed out that I qualified for the education expenses exception since I used part of the money for college tuition. Here's a quick list of the most common exceptions: - First-time home purchase (up to $10,000) - Qualified education expenses - Unreimbursed medical expenses exceeding 7.5% of AGI - Health insurance premiums while unemployed - Birth or adoption expenses (up to $5,000) - Disability - Being called to active military duty

Has anyone actually gotten their 1099-R forms for 2023 yet? My brokerage is taking forever and I'm trying to file early this year. Not sure if I should just estimate based on my account statements or keep waiting...