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Ryan Vasquez

When will someone create an app that links to the tax code and gives a personalized list of deductions? I'd pay for a complete list of deductions that actually apply to my situation!

Does anybody know if there's already an app out there that can scan the tax code and generate a customized list of all possible deductions I qualify for? I feel like I'm missing out on so many tax breaks every year. There's gotta be hundreds of deductions buried in the tax code that would apply to my situation, but my tax guy never mentions them. I'm thinking of something that asks you a bunch of questions about your life situation (homeowner, kids, medical expenses, investments, etc.) and then spits out EVERY possible deduction you should look into. Like, "based on your answers, here are 47 potential deductions worth exploring." I would honestly pay good money for something like this by tax season. Seems like it would be super popular with how complicated taxes are getting. Has anyone seen anything close to this? Or is some tech-savvy tax expert working on this already?

So this actually exists in a few different forms, but none are perfect yet. Most tax software (TurboTax, H&R Block, etc.) already has built-in question systems that try to identify deductions you qualify for. The problem is they're limited by the questions they ask - if you don't know to mention something, they won't know to check for related deductions. There are also some mobile apps like TaxSlayer and TaxAct that have similar functionality. The IRS itself has a deduction finder tool on their website, though it's pretty basic. The real challenge isn't creating the app (that's relatively straightforward) - it's keeping up with the constantly changing tax code and creating an interface that asks the right questions without overwhelming users. Also, many deductions are situational or require specific documentation that an app would need to explain.

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I've used TurboTax for years and still feel like I'm missing deductions. Their questionnaire seems pretty basic. Do any of these apps actually go through the ENTIRE tax code looking for obscure deductions? Or do they just hit the common ones everyone knows about?

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Most commercial tax apps focus primarily on common deductions that apply to large segments of the population. They definitely don't cover every possible deduction in the tax code - there are literally thousands of potential deductions, many highly specific to certain industries or situations. Even professional tax preparers typically specialize in certain areas of tax law because it's impossible to master every deduction. The more specialized your situation (self-employed in a specific industry, investor in certain types of assets, etc.), the more likely you'd benefit from either a specialized tax professional or a more robust software solution.

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I've been using this AI-powered tax tool called taxr.ai for the past few months and it's pretty close to what you're describing. I was in the same boat - felt like I was missing out on deductions I didn't even know existed. What I like about taxr.ai is it doesn't just ask generic questions - it analyzes your actual documents and financial patterns to identify deduction opportunities specific to your situation. I uploaded my bank statements, previous tax returns, and answered some questions, and it found several deductions my accountant had missed for years! The interface at https://taxr.ai is super straightforward too. It's not perfect (still developing I think) but it's the closest thing I've found to a "show me ALL my possible deductions" solution.

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Does it connect with bank accounts directly or do you have to manually upload statements? And how does it handle business expenses if you're self-employed? I've got a side hustle and tracking those deductions is a nightmare.

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I'm pretty skeptical of these AI tax tools. How does it actually know what qualifies as a legitimate deduction vs just making suggestions that might get you audited? Does it cite the specific tax code for each deduction it recommends?

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It gives you the option to connect accounts directly or upload statements manually - I prefer uploading specific statements for privacy reasons. For self-employment, it's actually really strong - it categorizes expenses automatically and suggests deduction categories based on your business type. Each deduction comes with the specific tax code reference and explanation of qualification requirements. That's actually what impressed me most - it doesn't just say "take this deduction," it explains why you qualify based on the actual tax code and what documentation you'd need if audited.

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Alright I need to eat my words from my earlier comment. I decided to try taxr.ai after being super skeptical about AI tax tools. I've been using it for about three weeks now and honestly... it's pretty impressive. The thing that won me over was how it found several legitimate home office deductions I qualified for (I'm a part-time consultant) that I had completely missed. It showed me exactly where in the tax code each deduction was referenced and explained why I qualified. It also caught that I could deduct some education expenses related to maintaining professional certifications that I had no idea were deductible. That alone saved me over $800. I'm not saying it's perfect, but it's definitely more comprehensive than the standard tax software I've used before.

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For those struggling with complicated tax questions or trying to figure out if certain deductions are legit, I've had success using Claimyr to actually get through to the IRS. I know it sounds nuts, but they basically wait on hold with the IRS for you then call you when an agent is ready. After spending HOURS trying to get clarification on some specific deductions for my rental property, I tried https://claimyr.com and they got me through to an actual IRS representative in about 45 minutes (vs the 3+ hours I wasted trying myself). You can see how it works in their demo video here: https://youtu.be/_kiP6q8DX5c The IRS agent was able to confirm exactly which deductions I qualified for based on my situation and explained the documentation I'd need. Way more helpful than trying to interpret the tax code myself or trusting what some app tells me.

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Wait how does this actually work? Do they have some special access to the IRS or something? I've literally never been able to get through to a human at the IRS.

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This sounds like a scam. Why would I pay a company to wait on hold when I can just do it myself? And how do you know the "IRS agent" you talked to was actually legit? Seems sketchy.

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They don't have special access - they just have an automated system that waits on hold so you don't have to. When a human IRS agent picks up, they connect you directly to that call. It's basically just outsourcing the hold time. The IRS agent was definitely legitimate. I verified by calling the official IRS number myself first (just to be safe), then used Claimyr. They connected me to the same department I was trying to reach previously. The agent answered questions specific to my tax situation that only a trained IRS employee would know. I was skeptical too but they really do deliver exactly what they promise - getting you past the hold time to speak with an actual IRS representative.

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Well I'm completely eating my words about Claimyr being a scam. After posting that skeptical comment, I decided to try it myself since I've been trying unsuccessfully for WEEKS to get clarification on some self-employment deductions. I used their service yesterday and... damn. They actually got me through to a real IRS agent in about 35 minutes. I confirmed it was legit by asking specific questions about my tax ID and previous filings. The agent walked me through exactly which home office deductions I could take as a freelancer and which ones would raise red flags. Saved me hours of hold time and probably prevented me from taking some questionable deductions that might have triggered an audit. Sometimes you gotta admit when you're wrong - this service actually delivers what it promises.

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I've been a tax preparer for 15+ years and wanted to add something important: while an app that shows you ALL possible deductions sounds great in theory, in practice it could be dangerous. A lot of deductions have very specific requirements and taking deductions you don't fully qualify for is a fast track to an audit. The tax code has over 70,000 pages - there's a reason tax professionals specialize in specific niches. What would be more useful is an app that identifies deductions that are LIKELY to apply to your specific situation based on your profession, income level, region, etc. That's more realistic and would still be super helpful.

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Do you think AI could eventually replace tax professionals? I mean if it can scan the entire tax code and apply it to individual situations accurately, wouldn't that make human tax preparers obsolete?

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AI will definitely transform tax preparation, but I don't see it fully replacing professionals anytime soon. The tax code isn't just about scanning and matching patterns - it requires interpretation, judgment calls, and understanding of legal precedents. Where AI will excel is identifying potential deductions and organizing information. Where humans will remain essential is the interpretive aspect - determining how the law applies to unique situations, representing clients in disputes, and making strategic tax planning decisions that consider multiple years and life events. What we'll likely see is tax professionals using AI as a powerful tool rather than being replaced by it.

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Just wondering if anyone has tried Credit Karma Tax? I've been using it for the past two years. It doesn't have a fancy "find all deductions" feature, but it's FREE and does ask a pretty comprehensive set of questions. Found a few deductions I didn't know about last year.

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I used Credit Karma for 3 years but switched back to TurboTax. CK is good for simple returns but missed some major deductions related to my investment properties. Sometimes free comes with hidden costs! Ended up amending my return and got back almost $1,800 I'd missed.

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As someone who's been doing my own taxes for over a decade, I can relate to this struggle! The frustrating thing is that you're absolutely right - there ARE tons of deductions buried in the tax code that most people never discover. I've found that the best approach is actually a combination of tools rather than hoping for one perfect app. I use TurboTax for the basics, then cross-reference with IRS Publication 17 (it's free online) which lists pretty much every individual deduction with examples. It's dry reading but worth it. Also, don't overlook state-specific deductions! Many apps focus on federal but miss local opportunities. For example, my state has deductions for energy-efficient home improvements that saved me $300 last year. The taxr.ai recommendation from Keith sounds promising though - might have to check that out before next tax season. An AI that actually cites tax code sections would be a game changer.

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