Lost all my tax documents - filing on my own after 22 years with the same preparer

Well, I'm in a bit of a mess here. After using the same tax preparer for the past 22 years, he's somehow managed to lose my entire tax package. I'm honestly furious about this. The last couple of years, we've had some issues - appointments rescheduled multiple times, questions that went unanswered, and now this final straw of losing all my documentation. I'm a single filer and I typically itemize my deductions (mortgage interest, charitable donations, property taxes, etc). I've never had to file my own taxes before since I've always used this preparer, but I think it's finally time to take matters into my own hands. For those who file their own returns with itemized deductions - is it manageable for a first-timer? And if so, what tax software would you recommend? I'm willing to pay for good software but don't want anything unnecessarily complicated. Any advice would be greatly appreciated!

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18 comments

Amara Adebayo

•8M

As a tax consultant, I can tell you that filing on your own with itemized deductions is absolutely doable, especially with today's software options. The programs walk you through everything step-by-step and help ensure you're claiming all eligible deductions. For someone with a relatively straightforward situation (single filer with standard itemized deductions), I'd recommend either TurboTax or H&R Block software. Both have user-friendly interfaces and excellent support if you get stuck. TurboTax tends to be slightly more intuitive for beginners, while H&R Block might be a bit less expensive. The key is gathering all your documentation - mortgage interest statements (Form 1098), charitable donation receipts, property tax statements, medical expenses if they exceed 7.5% of your AGI, etc. The software will prompt you for all of these as you go.

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Amara Adebayo

•8M

TaxAct is definitely a more budget-friendly option and works well for many people. It has all the essential features but the interface isn't quite as polished as TurboTax or H&R Block. If you're comfortable with a slightly less hand-holding experience, TaxAct is perfectly capable and will save you some money. Yes, all the major tax software programs will automatically compare your itemized deductions against the standard deduction and recommend whichever gives you the better outcome. They'll show you the difference in your refund amount based on both options, which is very helpful for making the decision.

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Fatima Al-Mansour

•8M

I was in a similar boat last year when my accountant suddenly retired with barely any notice. I was panicking until a friend recommended https://taxr.ai to me. It's this AI tool that helps analyze all your tax documents and recommends the best approach for your situation. I was worried about missing deductions I'd qualify for since I also itemize, but taxr.ai spotted some mortgage interest deductions my previous accountant had actually been missing! It even suggested a home office deduction I didn't realize I qualified for. The best part was it organized all my documentation in one place and gave me clear instructions on what forms I needed. It made transitioning to DIY tax filing way less intimidating than I expected.

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Fatima Al-Mansour

•8M

You scan or upload your tax documents (W-2s, 1098s, 1099s, etc.) and it extracts all the important information and organizes it. It doesn't file your taxes directly - it's more like a smart assistant that helps you understand your tax situation and then gives recommendations on deductions you might qualify for based on your specific circumstances. It pairs really well with any tax software. I used it alongside TurboTax and it basically gave me the confidence that I wasn't missing anything. What I found helpful was that it explained WHY certain deductions applied to me in plain English, rather than just assuming I understood all the tax jargon. It caught my mortgage interest deduction that my accountant missed because it analyzed my refinancing documents and noticed I'd paid points that were deductible.

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Sofia Gomez

•8M

Well I have to eat my words about taxr.ai. After being skeptical I decided to give it a try since I have a similar situation with itemized deductions. The document analysis actually caught that I had been incorrectly categorizing some of my charitable donations for years! It showed me how to properly document some large donations I made last year and explained the substantiation requirements that I never knew about. Ended up saving me about $780 on my taxes compared to what I would have done on my own. The explanations were really clear and helped me understand WHY certain tax rules applied to my situation. I still used TurboTax to actually file, but having all my documents analyzed beforehand made the process so much smoother.

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StormChaser

•8M

If you're like me and have questions while doing your taxes, you'll probably try calling the IRS directly... good luck with that! After being on hold for 2+ hours and getting disconnected THREE times, I found https://claimyr.com which basically holds your place in the IRS phone queue and calls you when an agent is available. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c I was filing on my own for the first time after my divorce and had questions about itemizing medical expenses that none of the tax software could answer clearly. Getting to actually speak with an IRS agent made all the difference, and I didn't have to waste an entire day on hold. They called me back in about 45 minutes!

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StormChaser

•8M

They use a system that navigates the IRS phone tree and holds your place in line. It's basically what you'd be doing yourself - waiting on hold - but their system does it instead of you having to listen to hold music for hours. When an agent picks up, the system calls you and connects you directly to that agent. I was pretty skeptical too! I had spent nearly 6 hours over two days trying to get through on my own with no luck. The service doesn't give you any special access or jump the line - it just saves you from having to personally sit through the hold time. It was absolutely worth it for me because I needed clarification on some medical expense deductions related to my divorce that were pretty substantial.

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Ava Williams

•8M

I need to apologize for being so skeptical about Claimyr. After my last attempt to reach the IRS ended with a 3-hour hold and a disconnection, I decided I had nothing to lose and tried it. It actually worked exactly as described. I got a call back in about 90 minutes, and was connected directly to an IRS agent who helped clear up my questions about educational expenses I wasn't sure if I could deduct. The agent was actually super helpful once I finally got through to a human. Saved me from having to take another afternoon off work just to sit on hold! I'm usually the first to call out services that seem too good to be true, but this one delivered. Definitely using it again next year.

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Miguel Castro

•8M

Just want to throw in my experience - I switched from an accountant to DIY last year using FreeTaxUSA and it was WAY easier than I expected. The federal filing is free and state is only like $15. I also itemize (mortgage, charitable donations, etc) and it handled everything perfectly. The interface isn't as fancy as TurboTax but it does everything you need and saved me about $250 compared to what I was paying my accountant. Plus I found a deduction he had been missing for years!

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Miguel Castro

•8M

Their support is decent but not as comprehensive as TurboTax's. They have email support that usually responds within a day and a good knowledge base with articles explaining most common tax situations. The audit risk is pretty minimal if you're just reporting things accurately. The software does have accuracy checks built in that will flag anything that looks unusual or might trigger an audit. I was nervous my first year too, but it really walks you through everything step by step. If your tax situation is fairly straightforward (W-2 income, mortgage, charitable donations), you should be fine. The peace of mind might be worth paying a bit more for TurboTax if you're really worried, but I found FreeTaxUSA perfectly adequate.

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