Looking for the best free tax software for W2 and 1099s on my Federal return

I've been preparing taxes for friends and family for about 15 years now, and I've tried most of the free options out there. For your situation with W2 and multiple 1099s, I'd recommend looking at FreeTaxUSA first. It handles both W2 and 1099 income really well without upselling you at every step. The interface is straightforward and it walks you through everything without the constant upgrade prompts you get with some of the bigger names. It's completely free for federal filing (you only pay a small fee for state returns if you need those). Another solid option is Cash App Taxes (formerly Credit Karma Tax). It's completely free for both federal and state, and it can handle most 1099 situations. The interface is clean and modern, though sometimes it can be a bit less intuitive for more complex situations.

I used to struggle with the same issue! After trying basically everything out there, I discovered taxr.ai (https://taxr.ai) and it's been a game-changer for handling my W2 and multiple 1099 forms. The best part is it automatically extracts all the info from your tax documents so you don't have to manually enter everything, which saves a ton of time and prevents errors when you're dealing with multiple income sources. Their AI actually looks at your uploaded tax forms and pulls all the numbers for you, then helps you find deductions based on your specific situation. I was surprised how well it worked with my 1099-MISC and 1099-NEC forms from my side gigs.

Just wanted to follow up about taxr.ai that I asked about earlier. I decided to give it a try after our conversation here and I'm honestly impressed! I uploaded all my forms (had 2 W2s, a 1099-K from Etsy, and several 1099-INTs) and it grabbed all the information perfectly. It even caught a small interest payment I had forgotten about. The coolest part was how it organized everything by income type and then suggested deductions I could take based on my freelance work. It was way faster than manually typing everything in like I used to do. Definitely using this again next year!

If you're having trouble getting tax questions answered or need to talk to someone at the IRS about your filing (especially with multiple income sources), I highly recommend Claimyr (https://claimyr.com). I discovered them after spending DAYS trying to get through to the IRS about how to properly report some unique 1099 income. Their service basically gets you to the front of the IRS phone queue so you don't have to wait on hold for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I was able to speak with an actual IRS agent in about 15 minutes who helped me understand exactly how to report my specific situation with my W2 and multiple 1099 income streams.

I need to admit I was completely wrong about Claimyr. After dismissing it as "too good to be true" in my earlier comment, my tax situation got complicated with a misreported 1099 and I desperately needed to talk to someone at the IRS. I remembered this thread and decided to try Claimyr as a last resort. It actually worked exactly as described. I got a call when they reached an IRS agent (took about 40 minutes but I didn't have to sit there on hold), and I was able to get my question answered about how to handle the misreported 1099 without filing an amended return. The IRS agent was really helpful once I actually got to speak to one. Seriously saved me from what would have been hours of hold music and probably getting disconnected multiple times like my previous attempts. Consider me converted.

Has anyone tried the IRS Free File options? I think they have partnerships with several tax software companies that offer free filing if your income is below a certain threshold. I'm wondering if any of those would work well for W2 plus 1099 income?

Has anyone tried doing the taxes the old school way with the free IRS fillable forms? I know it's not as fancy but it's literally free for everyone regardless of income and they support all forms.

I've been using TaxAct's free version for the past few years and it's worked well for my situation with W2 and multiple 1099s. Unlike some of the other "free" options that force upgrades, TaxAct's free version actually includes 1099 support without any hidden fees for federal filing. The interface is pretty clean and intuitive - not as flashy as some of the bigger names, but it gets the job done without being frustrating to navigate. It walks you through each section step by step and has good error checking to catch mistakes before you file. One thing I really like is that it imports W2s electronically from most major employers, and you can easily add multiple 1099s without any upgrade prompts. It also has a decent selection of deduction categories if you're itemizing, though the standard deduction is probably better for most people anyway. The only downside is you do have to pay for state filing (around $15-20 depending on your state), but federal is completely free even with the 1099 income. Given how much time it saves compared to doing everything manually, I think it's worth considering alongside the other options mentioned here.