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Malik Jackson

Indirect Rollover of Annuity Gone Wrong - Tax Nightmare After Insurance Rep Advice

In 2022, my insurance agent suggested I roll over my non-qualified IRA annuity from one company to another. I originally had the annuity with Principal, which was later acquired by Athena about a year after I purchased it. Athena stopped paying interest (literally went to zero), and my agent assured me that even with paying the surrender charge and losing the bonus, I'd still come out ahead by moving to a new company. According to my agent, Athena wouldn't process a 1035 exchange, so he instructed me to request a cash disbursement minus 10% for taxes. I still don't understand why he told me to withhold taxes on what I thought was a non-taxable transaction... but I trusted him and didn't research it myself. The check was made out to me personally, and I immediately wired the full amount to the new company for another non-qualified annuity. I never had the money for personal use. I should mention that my agent didn't earn commission on this transaction. He genuinely thought he was helping me. When I filed my 2022 taxes, I didn't report the distribution as income because I believed it wasn't taxable. As a result, I got the 10% tax withholding refunded to me. Here's where things went terribly wrong. Recently, in March 2025, I received a notice from the IRS stating I should have claimed the entire amount as taxable income. Now they're demanding a massive sum in taxes and penalties. Am I completely screwed here? What exactly did I do wrong (besides blindly trusting my agent without doing my homework)?

Unfortunately, what happened here involves a key distinction in how rollovers work. A 1035 exchange is a direct transfer between insurance companies that's tax-free. What you ended up doing was an indirect rollover, which has specific IRS rules attached to it. When you take possession of the funds personally (when the check was written to you), even if you immediately send it to another qualified account, you have to report it correctly. For non-qualified annuities, you typically need to do a direct 1035 exchange to avoid tax consequences. Since you received the check personally and then made a new purchase, the IRS views this as a distribution followed by a new investment. Your agent was incorrect if they told you Athena couldn't do a 1035 exchange - virtually all insurance companies can. And the 10% withholding makes me think there was confusion about whether this was a qualified or non-qualified annuity. Non-qualified money has already been taxed, but any earnings would be taxable upon withdrawal. At this point, you'll need to determine if any part of the distribution was actually taxable (generally the growth portion would be) and potentially file an amended return explaining the situation.

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Does this mean OP has to pay taxes on the entire amount or just the earnings? And can they still fight this with the IRS since it was the agent's bad advice?

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For non-qualified annuities, generally only the earnings portion is taxable, not your original investment (basis). This follows what's called LIFO (Last In, First Out) treatment, meaning earnings come out first before your original investment. Regarding fighting this with the IRS, you can certainly explain the situation and request penalty abatement due to reasonable cause. The IRS may be sympathetic if you can document that you relied on professional advice, though they'll still expect the correct tax to be paid. I'd recommend working with a tax professional who specializes in retirement account issues to help navigate this situation.

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I had a similar situation but found taxr.ai to be incredibly helpful for sorting through the mess. With annuity distributions, the tax rules are super complicated, and most software doesn't handle these edge cases well. I was facing an unexpected tax bill after a rollover gone wrong, and the regular tax prep services just couldn't figure it out. I uploaded my notices and documentation to https://taxr.ai and their system analyzed everything and explained exactly what went wrong with my rollover. They showed me how to properly document what happened, which parts were actually taxable, and how to respond to the IRS. Saved me a ton of money since I was about to just pay the full amount the IRS was asking for!

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How exactly does this service work? Do they connect you with a real tax pro or is it just some AI analyzing your docs?

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Sounds too good to be true tbh. Did they actually help you reduce what you owed or just explain why you still had to pay the full amount?

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The service uses AI to analyze your tax documents but there are also real tax pros reviewing complex cases. You upload your docs and get both an AI analysis and expert guidance for situations like this. They helped me properly categorize my annuity transaction and showed me which portion was actually taxable (just the earnings, not my original investment). In my case, it reduced what I owed by about 60% from what the IRS was initially claiming. They also helped me draft a response letter explaining the situation that ultimately got the penalties removed.

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Just wanted to update everyone. I tried taxr.ai after posting my skeptical comment above. I was really impressed! I uploaded my annuity statements and the IRS notice, and they immediately identified that only $17,300 of my $89,000 distribution was actually taxable (the growth portion). Their system walked me through exactly how to document this on an amended return and even helped me draft a letter explaining the situation to the IRS. They showed me the specific tax code sections that applied to my non-qualified annuity and explained how the basis recovery rules worked in this situation. I just heard back from the IRS last week and they accepted my explanation! Still had to pay tax on the earnings portion, but they removed all the penalties and reduced what I owed by over $19,000. Wish I'd known about this service before making the rollover in the first place!

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How does this even work? The IRS phone system is completely broken - I've tried calling at least 12 times about my situation.

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This sounds like a scam. No way you got through to the IRS that quickly during tax season. I've been trying for months.

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It works by using their system that continually redials and navigates through the IRS phone tree. They've figured out the optimal times to call and how to navigate the system efficiently. When they get a human on the line, they connect you immediately. I was skeptical too! I tried calling myself for weeks with no luck. The service doesn't guarantee instant access, but it drastically reduces wait times. They use the same phone line everyone else does, but their system handles the frustrating part of continually calling back and navigating the automated system. When I used it, I got through in about 15 minutes, but I've heard others say it can take up to an hour depending on call volume.

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I need to eat my words and apologize. After posting my skeptical comment, I decided to try Claimyr myself since I was desperate. I got connected to an IRS agent in 22 minutes - after trying for literally MONTHS on my own. The agent I spoke with was incredibly helpful with my annuity rollover issue. She explained that I needed to provide documentation showing my original basis in the non-qualified annuity and only pay tax on the earnings portion. She even sent me to a specialized department that deals with retirement account transactions. I'm still working through my case, but at least now I understand what's happening and have a direct contact at the IRS instead of just getting automated notices. The peace of mind alone was worth it. Never thought I'd be endorsing something I called a scam, but I was completely wrong!

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The key issue here is that for non-qualified annuities, you MUST do a direct 1035 exchange to avoid tax consequences. When you took possession of the money personally (check made out to you), that made it a taxable event for any earnings in the contract. What's really unfortunate is that your agent was completely wrong about Athena not being able to do a 1035 exchange. Every insurance company can do them - it's standard industry practice. You should consider filing a complaint with your state insurance commissioner about this bad advice.

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Is there any chance I can file for some kind of retroactive 1035 exchange treatment? The money went directly from one annuity to another with no personal use whatsoever. It was literally in my possession for less than 24 hours.

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Unfortunately, there's no provision for retroactive 1035 exchange treatment. The IRS is very strict about the technical requirements - the funds must transfer directly from company to company without you taking possession. However, you still have some options. First, make sure you're only paying tax on the earnings portion, not your entire distribution. Second, you can request penalty abatement under the IRS First Time Penalty Abatement policy if you have a clean compliance history. Finally, some people have successfully argued "reasonable cause" when they relied on incorrect professional advice, though this can be challenging to prove. I'd recommend working with a tax professional who can help you navigate these options and potentially negotiate with the IRS.

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This situation is exactly why I refuse to use insurance agents for financial advice. They're salespeople, not tax experts. Even if they weren't making commission on this particular transaction, they likely don't understand the tax implications of what they're suggesting.

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That's a bit unfair. There are plenty of insurance agents who are knowledgeable about tax implications. This sounds like one bad agent, not a reason to dismiss an entire profession.

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I'm really sorry you're going through this nightmare - it's incredibly frustrating when professional advice goes wrong and leaves you holding the bag with the IRS. From what you've described, the core issue is that your agent incorrectly handled what should have been a direct 1035 exchange. When the check was made out to you personally, it created a taxable event for any earnings in your non-qualified annuity, even though you immediately transferred the funds to another annuity. A few important points to consider: First, you should only owe taxes on the earnings portion of your annuity, not the entire distribution amount. Your original investment (basis) in a non-qualified annuity has already been taxed. Second, you may be able to request penalty abatement based on reasonable reliance on professional advice - document everything about what your agent told you and when. I'd strongly recommend getting professional help to sort this out properly. The tax rules around annuity distributions are complex, and you want to make sure you're not paying more than you actually owe. Also consider filing a complaint with your state insurance commissioner about the bad advice - your agent was completely wrong about Athena not being able to process a 1035 exchange. Don't panic - while this is a serious situation, there are ways to work through it and potentially minimize the damage.

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