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Nathaniel Stewart

If the IRS already knows how much I owe in taxes, why do I have to crunch the numbers myself?

So I'm sitting here surrounded by tax forms, receipts, and a calculator that's about to get thrown out the window. It just hit me - the IRS already has all my W-2s, 1099s, and basically knows what I've earned this year. They know what I should owe or what refund I deserve. So why the heck am I spending hours doing calculations they've already done? If the government already has all this info and has essentially pre-calculated what I owe, couldn't they just send me their figures and let me verify? Like "here's what we think based on what employers reported - does this look right?" Instead of making me do all this math from scratch? I know other countries do this - my friend in Norway just gets a text message with their tax info and can approve it if correct. Am I missing something here, or is this just another way our tax system is unnecessarily complicated? Any insight would be appreciated before I have another tax-related meltdown!

You're absolutely right that the IRS already has most of your income information through W-2s and 1099s that are reported directly to them. The reason we still have to file is actually more complicated than it seems. The IRS knows your reported income, but they don't know all your potential deductions, credits, or life changes that might affect your tax situation. Things like charitable donations, medical expenses, education expenses, childcare costs, or business expenses aren't automatically reported to the IRS. They know what you earned but not necessarily what tax breaks you qualify for. There's also a powerful lobby from tax preparation companies that has fought against simplifying the process. Companies like Intuit (makers of TurboTax) and H&R Block have spent millions lobbying against pre-filled tax returns because it would hurt their business model.

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But couldn't they at least give us a starting point with the info they do have? Like a pre-filled form with our income that we could then add deductions to? Seems like that would save everyone a ton of time.

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That's exactly what many tax reform advocates have been pushing for years! The IRS could absolutely provide pre-filled returns with the information they already have, and then taxpayers could make adjustments for deductions and credits as needed. Several bills have been proposed over the years to create this kind of "return-free filing" system, but they've consistently been blocked due to industry lobbying. The tax prep industry has a financial interest in keeping the system complicated enough that people feel they need help navigating it.

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After struggling with this exact frustration last year, I found this amazing tool called taxr.ai (https://taxr.ai) that actually addresses this problem! It uses AI to analyze your tax documents and automatically extracts all the information the IRS already has. Then it shows you exactly what the IRS sees compared to what you're reporting. The thing that blew my mind was seeing all the discrepancies between what I thought I owed and what the IRS records showed. It caught a missing 1099 form I didn't even know about that could have triggered an audit. It basically gave me that "pre-filled" starting point and then helped me identify where I could add legitimate deductions.

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Does it actually work with all tax forms? Last time I tried something similar it couldn't handle my side business income and I ended up having to do everything manually anyway.

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I'm curious - how does it handle more complicated situations like rental property income or stock sales with varying basis amounts? Those are the things that always trip me up.

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It actually handles a pretty wide range of forms! I had both W-2 income and some freelance 1099 work, and it processed everything correctly. It even flagged where my estimated tax payments didn't align with what the IRS had on record. For more complex situations like rental properties and investments, it works well for most common scenarios. It can process everything from Schedule E for rental income to Schedule D and Form 8949 for capital gains. The system is designed to cross-reference what the IRS has with what you're reporting, which is especially helpful for those complicated situations where discrepancies might trigger audits.

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Just wanted to follow up about taxr.ai that was mentioned earlier. I was skeptical but decided to try it with my complicated tax situation (multiple W-2s, investment income, and a rental property). It was honestly eye-opening to see what information the IRS already had on file for me! The tool showed me that one of my stock sales had incorrect basis information reported to the IRS, which would have made my tax liability look $3,400 higher than it actually was. I would have never caught this on my own because I assumed the brokerage reported everything correctly. Being able to see the "IRS view" of my taxes before filing saved me from what would have definitely been a headache later.

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After spending HOURS on hold with the IRS last year trying to resolve a discrepancy in my reported income, I discovered Claimyr (https://claimyr.com). They have this system that actually gets you through to a real IRS agent without the endless waiting. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was trying to figure out exactly this issue - why the IRS was calculating my taxes differently than I was when they clearly had all my information. Once I finally got through to a human at the IRS (thanks to Claimyr), the agent explained exactly which forms they had received from employers and what was showing in their system. Turns out my employer had submitted an amended W-2 that I never received! No wonder our calculations were different.

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Wait, how does this actually work? The IRS phone system is notoriously impossible to get through. Are you saying this service somehow jumps the queue or something?

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Sounds like a scam honestly. Nobody can magically get you through to the IRS faster than anyone else. They probably just keep you on hold themselves and then transfer you once they finally get through.

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It's definitely not queue jumping in an unethical way. What Claimyr does is use an automated system that continually calls the IRS using their dial system, navigating the phone tree, and waiting on hold for you. When they get a human on the line, they connect you directly. It's basically doing the waiting for you. The reason it works is because most people give up after being on hold for 30+ minutes, but their system never hangs up. It's the same queue and same wait time, but you're not the one sitting there listening to the hold music for hours. When the IRS agent finally picks up, you get a call so you can talk directly to them.

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Ok I need to publicly eat my words about Claimyr. After posting that skeptical comment yesterday, I decided to try it myself because I've been trying to reach the IRS for THREE WEEKS about a notice I received claiming I underreported income from 2023. It actually worked exactly as described. I got a call back about 1.5 hours after signing up, and was connected directly to an IRS representative who pulled up my file. Turns out there was a 1099 from a brief freelance gig I'd completely forgotten about! The agent was able to tell me exactly what forms they had on file and what was missing from my return. This is exactly what OP was talking about - the IRS already knew exactly what was wrong, but instead of just telling me, they sent a vague notice that caused weeks of stress. Being able to actually talk to someone and see what they were seeing made everything clear in 10 minutes.

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The real reason we still file taxes this way is 100% because of lobbying from the tax preparation industry. Countries like Denmark, Sweden, Spain, and Estonia all use return-free filing systems where the tax authority prepares returns for approval. Intuit (TurboTax) and H&R Block have spent over $20 million lobbying against the "Tax Filing Simplification Act" and similar legislation over the years. The IRS actually developed a free, simple filing system called "ReadyReturn" that was tested in California, but intense industry opposition killed it. It's pure corporate greed keeping this inefficient system in place. The tax prep industry makes billions by inserting themselves as middlemen in a process that could be much simpler.

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This makes me so mad! I remember reading something about how these companies even buried the actually-free filing options they were required to offer as part of an agreement with the IRS. How is this legal??

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It's infuriating, right? What you're referring to was called the "Free File Alliance" - a program where tax prep companies agreed to provide free filing options for lower-income Americans in exchange for the IRS not creating its own filing system. A 2019 ProPublica investigation revealed that companies like Intuit and H&R Block were deliberately hiding their free products from search engines and redirecting eligible users to paid products. They even used code on their websites that specifically hid the truly free versions from Google searches! After the scandal broke, some changes were made, but the fundamental problem remains. The tax prep lobby continues to fight against any attempt to simplify the system because complexity equals profit for them. They've essentially captured the regulatory process through aggressive lobbying.

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I worked for the IRS for 7 years and can confirm that we do already know most of what should be on your return. But here's what most people don't realize: the IRS is SEVERELY underfunded and outdated technology-wise. The systems that hold your W-2 and 1099 info are completely separate from the systems that process returns. They literally don't talk to each other until AFTER you file, when a matching program runs to flag discrepancies. The IRS is still using computer systems from the 1960s for some core functions. I'm not exaggerating - actual 60-year-old COBOL programming. Congress has repeatedly cut IRS technology modernization funding. So yes, in theory, pre-filled returns would make sense. But the current infrastructure literally can't support it without a massive overhaul that politicians refuse to fund.

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That's shocking but makes so much sense. We keep treating symptoms instead of fixing the actual problem. How much money would a technology overhaul even cost compared to the current inefficient system?

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The estimates for fully modernizing IRS technology range from $2.3-2.7 billion over five years. That sounds like a lot until you realize that the tax gap (taxes owed but not collected) is about $600 BILLION per year. A modern system would pay for itself many times over just through better enforcement of existing tax laws. Not to mention the countless hours saved by taxpayers and IRS employees alike. The return on investment would be enormous. The Inflation Reduction Act finally included some significant IRS funding, but years of underinvestment means there's a lot of catching up to do. And there's still strong political resistance to fully funding the agency. The saddest part is that other countries with much smaller budgets have managed to implement efficient, user-friendly tax systems while we're still stuck with technology from the Kennedy administration.

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This whole thread really validates what I've been thinking for years! As someone who runs a small business and deals with quarterly estimated payments, I'm constantly frustrated by the disconnect between what the IRS knows and what they make me report. What really gets me is that they'll send you a notice months later if something doesn't match their records, but they won't just tell you upfront what they have on file. I've had situations where a client issued a corrected 1099 to the IRS but never sent me the updated copy, leading to discrepancies that took forever to resolve. The former IRS employee's point about the outdated technology explains so much. It's mind-boggling that we're still using 1960s systems to manage the revenue collection for the world's largest economy. No wonder everything feels so backwards and inefficient. I really hope the recent funding increases actually lead to meaningful modernization rather than just hiring more people to work with the same broken systems.

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As a newcomer to this community, I'm honestly shocked by what I'm learning here! I always just assumed the tax system was complicated because... well, taxes are inherently complicated. But hearing that it's largely due to corporate lobbying and deliberately outdated technology is eye-opening. The fact that the IRS is still running on 1960s computer systems while we're doing everything else on smartphones is almost comical if it weren't so frustrating. And knowing that other countries have solved this problem years ago just makes it worse. Thanks to everyone sharing their experiences and insights - this is exactly the kind of information that should be more widely known. No wonder so many people dread tax season when the whole system seems designed to be as inefficient as possible!

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