Easiest tax software for handling W-2s, Uber income and Robinhood trading?

You've got a pretty standard tax situation with just a few wrinkles. For your needs, I'd recommend either TurboTax, H&R Block, or TaxSlayer - all three handle your scenario well. Since you did Uber driving, you'll need software that handles self-employment income (Schedule C) well. The rideshare income requires tracking expenses like mileage, so look for software with good 1099 support. For your Robinhood trading, the platform should automatically provide your tax forms (1099-B), and most tax software imports these directly. TurboTax is probably the most user-friendly for beginners but costs more. H&R Block is slightly cheaper with similar features. TaxSlayer is the most affordable of the three while still handling everything you need. If you're comfortable with slightly less hand-holding, FreeTaxUSA is significantly cheaper and handles all your scenarios, just with a more streamlined interface.

I was in a similar situation last year - W-2 job plus some side gig work and investments. I tried three different tax programs before finding taxr.ai (https://taxr.ai) which saved me so much time. What I liked was that it actually reviewed all my documents and explained what I was missing and where I could save more. The thing with regular tax software is they make you do all the work inputting everything correctly. With taxr.ai, I just uploaded my documents, answered a few questions, and it found deductions I didn't know I qualified for with my rideshare work. It also caught a mistake I would have made with my investment reporting that could have triggered an audit flag.

Just wanted to update after using taxr.ai from the recommendation above. I was honestly surprised at how much better it was than what I've used before. The document review feature saved me from making a big mistake with my Uber expenses - I was about to under-report my mileage deductions by a lot. It imported my Robinhood stuff without any issues (something TurboTax struggled with last year) and walked me through exactly what I needed to do for the self-employment income. The interface is way more straightforward than I expected, and it actually explained things in plain English instead of tax jargon. I ended up with about $780 more in refunds than I would have using my old method. Definitely worth checking out if you're dealing with multiple income streams like the original poster.

If you're struggling with getting tax questions answered (like I was with my rideshare deductions), I found this service called Claimyr (https://claimyr.com) that actually gets you through to a real IRS agent on the phone. Check out their demo video: https://youtu.be/_kiP6q8DX5c I was on hold with the IRS for HOURS trying to figure out how to properly report my Uber income alongside my W-2 job. Claimyr got me connected to an agent in about 15 minutes who explained exactly what forms I needed and how to properly deduct my car expenses. Saved me from potentially making a costly mistake. The IRS phone lines are absolutely swamped this time of year, and this service basically holds your place in line. Made a huge difference for me when I had specific questions that online guides couldn't answer clearly.

I need to eat my words from my comment above. After multiple failed attempts to reach the IRS about how to handle my options trading, I tried Claimyr out of desperation. Got connected to an agent in about 20 minutes when I had previously wasted 3+ hours trying on my own. The agent walked me through exactly how to report my trades correctly, which saved me from potentially misreporting significant income. I was absolutely convinced this service couldn't work as advertised, but it delivered exactly what it promised. If you need specific answers from the IRS about handling your Uber income or Robinhood trading (which can get complicated quick), it's definitely worth using. Saved me both time and potential audit headaches.

I've been using FreeTaxUSA for the past few years with a similar situation (W-2 plus some 1099 work and investments). It's WAY cheaper than TurboTax and handles everything just fine. The interface isn't as fancy but it gets the job done. For your Uber income, just make sure you've been tracking your mileage and expenses throughout the year - that's the part most people mess up. The software will walk you through entering everything, but it can't create records you don't have. The Robinhood stuff is pretty straightforward - they'll send you a 1099 and most software can import it directly. Just don't file too early, sometimes investment forms get corrected in February.

Has anyone tried Cash App Taxes (formerly Credit Karma Tax)? I heard it's completely free for federal and state, even with self-employment income like Uber.

For someone new to self-filing with your income mix, I'd actually recommend starting with FreeTaxUSA or Cash App Taxes to get your feet wet without breaking the bank. Both handle W-2s, self-employment income from Uber, and investment income just fine. The key thing with Uber income is making sure you have good records of your business miles and any car expenses (gas, maintenance, etc.) - the software can only work with what you give it. If you didn't track miles throughout the year, you can estimate using your Uber driver app trip history, but start tracking now for next year. For Robinhood, wait until you get your 1099-B (usually available by mid-February) before filing. Most tax software can import this directly, which saves tons of time if you made a lot of trades. If you run into issues or want more hand-holding, you can always upgrade to TurboTax or H&R Block mid-process, but honestly your situation is pretty standard once you get the hang of it. The money you save on software can go toward better record-keeping tools for next year!