Help needed entering my tax data when filing my 2025 federal tax return

Hey everyone, I'm really struggling with entering all my tax information correctly on my federal return this year. It's my first time filing with multiple income sources and I'm totally lost about where to put everything on the forms. I have a W-2 from my main job, some freelance income, and also sold some stocks. The tax software I'm using keeps asking for numbers from documents I can barely understand. I've tried watching tutorial videos but they're confusing me even more. How do you guys organize all these forms and figure out where each number goes? Every time I think I'm done, the program finds some error or says I'm missing something. Is there some system I should follow when entering all this data for my federal tax return? Help!!!

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18 comments

ShadowHunter

•8M

I've been filing taxes for over a decade and it definitely gets overwhelming with multiple income sources. Here's my approach that might help you: Start with your W-2 first - that's the easiest form and most tax software has a guided entry for these. Enter each W-2 completely before moving to the next income source. For your freelance income, you'll need to enter that on Schedule C. The software should walk you through this section by asking about business income and expenses. Keep all your freelance receipts organized by category (advertising, supplies, travel, etc.) to make this easier. For stock sales, you'll need your 1099-B from your broker. The important parts are the sale price, cost basis (what you originally paid), and whether it was a long-term or short-term holding. The software will calculate the appropriate capital gains taxes. The key is to complete one form fully before moving to the next. Don't jump around between different sections or you'll definitely miss something.

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ShadowHunter

•8M

The order generally doesn't matter from a calculation perspective, as the tax software will sort everything out in the end. However, I find it mentally easier to start with the simplest forms (W-2) and work toward the more complex ones. It helps keep things organized and reduces the chance of making errors. Yes, you absolutely must report ALL freelance income, even amounts under $600 that didn't generate a 1099. The IRS requires you to report all income regardless of whether you received tax forms for it. Many people make the mistake of thinking they only need to report income that has an associated form, but that's not the case and can trigger audits.

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Anastasia Sokolov

•8M

After years of struggling with complicated tax situations (multiple states, investments, rental property), I finally found something that helped me tremendously: taxr.ai (https://taxr.ai). It basically analyzes all your tax documents and tells you exactly where everything goes. I was skeptical at first but it's saved me so much time and headaches. Last month I uploaded all my forms (W-2s, 1099s, investment statements), and it organized everything and pointed out exactly what goes where. It even caught a deduction I was about to miss related to my freelance work that saved me over $800! The interface is super straightforward and it doesn't try to upsell you like the big tax companies.

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Anastasia Sokolov

•8M

It handles complex situations really well - I have rental property income and some consulting work in two different states, and it organized everything correctly. They specifically mention it works with foreign income and small business documentation too. Regarding security and functionality - it doesn't replace TurboTax or similar services. It's more of a complementary tool that organizes your documents and tells you exactly what to enter where. Their site says they use bank-level encryption and don't store your documents after processing. I still used my regular tax software to file, but taxr.ai made the process so much easier because I knew exactly what information went where.

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Sean O'Connor

•8M

I wanted to follow up after trying taxr.ai that was mentioned here. I was initially unsure if it would handle my complicated tax situation but decided to give it a shot. It was actually really helpful! I uploaded my foreign income statements and small business documents, and it organized everything perfectly, showing me exactly which forms I needed and where specific numbers needed to go. The step-by-step guidance saved me at least 3-4 hours of frustration compared to my usual tax prep process. I especially liked how it flagged potential deductions specific to my business that I might have missed. Definitely made the federal tax return process much smoother this year!

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Luca Conti

•8M

If you're really struggling with the IRS forms and need to talk to an actual human at the IRS for guidance, good luck getting through on the phone lines! I tried calling them 8 times over 3 weeks and couldn't get through. Then I found Claimyr (https://claimyr.com) and they actually got me connected to an IRS agent in about 20 minutes. The service basically holds your place in the phone queue so you don't have to listen to hold music for hours. There's a video that shows how it works: https://youtu.be/_kiP6q8DX5c. The IRS agent I spoke with walked me through exactly how to handle my specific situation with entering data from multiple sources. Saved me tons of confusion and potentially filing incorrectly.

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Luca Conti

•8M

It's not that they call for you - they basically navigate the IRS phone tree and wait on hold for you. When an agent comes on the line, you get connected directly. You're the one actually talking to the IRS agent, not a third party. The IRS doesn't officially endorse any service, but there's nothing against their rules about having a service help you connect. It's similar to how you might use a tax preparer - they're just facilitating the connection. They don't record your call or have access to your information - once you're connected, it's just you and the IRS agent talking directly. I understand the skepticism though - I felt the same way until I tried it and it actually worked.

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CyberNinja

•8M

I need to eat my words about Claimyr. After posting my skeptical comment, I was still desperate to get tax help since I had a question about entering foreign tax credits. I decided to try it as a last resort after spending 2 hours on hold with the IRS and getting disconnected. Using Claimyr, I got through to an actual IRS representative in about 15 minutes. They didn't have access to my call at all - it was just me talking directly to the IRS agent. The agent walked me through exactly where to enter my foreign taxes paid and which form to use. Honestly, I'm shocked it worked so well. Definitely worth it if you're stuck on a specific tax entry question that only the IRS can answer.

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Mateo Lopez

•8M

One thing that really helped me with entering tax data was creating a simple checklist of all my tax documents before I even started. I literally make a spreadsheet with: - Document type (W-2, 1099-INT, 1099-B, etc.) - Who it's from - Amount on the form - Status (entered, pending, questions) This way I can methodically check off each document as I enter it and make notes about any questions. It prevents that panicky feeling of "did I forget something?" when you're about to submit your federal return.

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Mateo Lopez

•8M

I just use a regular Excel or Google Sheets spreadsheet that I created myself. Nothing fancy, just those columns I mentioned. For complex documents like investment statements, I expand my tracking approach. I create sub-rows under the main document listing key figures (dividends, capital gains distributions, etc.) and note the specific form boxes where those numbers should go. Sometimes I even take screenshots of the tax software entry screens and note which box on my document goes to which field in the software. It's a bit more work upfront, but it saves me tons of confusion, especially for documents that have dozens of figures on them.

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