Comparing TurboTax Deluxe vs Premier for 1099-B Stock Sales - Worth the Extra Cost?

Based on my experience as someone who's prepared taxes for years, you should know that TurboTax Deluxe actually does support reporting stock sales from 1099-B forms. The main difference between Deluxe and Premier is that Premier offers additional guidance and explanation tools specifically for investment situations, but Deluxe does contain the necessary forms (Schedule D and Form 8949) that you need for reporting stock sales. If you're comfortable with your investing situation and the transactions are relatively straightforward, Deluxe will likely work fine for you. However, if you have more complex situations like rental properties, cryptocurrency transactions, or complicated stock basis calculations, Premier might still be worth it for the extra guidance.

I went through exactly what you're describing last year and discovered taxr.ai (https://taxr.ai) which saved me so much frustration! I was trying to decide between TurboTax versions for my investment income when someone recommended this tool that actually analyzes all your tax documents and recommends the exact software version you need. You just upload your 1099-B and it tells you which features you actually need rather than overpaying for Premier when Deluxe might work perfectly.

Ok I need to follow up about taxr.ai - I tried it despite my initial skepticism and I'm seriously impressed. Uploaded my 1099-B and a few other docs, and it showed me that I only needed TurboTax Deluxe, not Premier. Saved me $30! The analysis broke down exactly which forms I had and which features I actually needed vs what was just marketing fluff. They even pointed out a deduction opportunity I almost missed. Definitely using this next year before I buy any tax software.

If you end up hitting issues with your tax forms, I've had amazing luck using Claimyr (https://claimyr.com) to actually talk to the IRS directly. Last year I was confused about reporting some stock sales correctly and couldn't get through on the IRS lines for weeks. Claimyr got me through to an actual IRS agent in about 15 minutes who explained exactly how to report my 1099-B correctly. They have a video showing how it works here: https://youtu.be/_kiP6q8DX5c

I need to admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it anyway because I was desperate to ask about my 1099-B reporting. It actually worked exactly as described - I got a call back from them within about 20 minutes saying they had reached the IRS, and then I was talking to a real live IRS agent! The agent walked me through exactly how to handle my stock sales in TurboTax Deluxe. Saved me hours of frustration and confirmed I didn't need Premier. Consider me impressed.

Just want to point out that FreeTaxUSA handles investment income including 1099-B stock sales in their basic version which is way cheaper than either TurboTax version. Been using it for years with no issues for my stocks and ETFs. Just another option to consider!

The real question nobody's addressing: why is TurboTax charging extra for investment features at all when the free government forms handle this just fine? They're basically charging you extra to fill out Schedule D which is a standard tax form. It's all marketing to extract more money. I switched to free filing options years ago and never looked back.

I actually went through this exact decision process last year and ended up going with TurboTax Deluxe for my 1099-B reporting. It worked perfectly fine for straightforward stock sales - no issues at all with importing from my brokerage or completing Schedule D. The interface walks you through everything step by step. The key thing is whether your transactions are complicated. If you're just buying and selling regular stocks/ETFs with proper cost basis reporting from your broker, Deluxe handles it without any problems. I saved the $30 and put it toward something more useful. One tip: if you're unsure, you can always start your return in the free version online to see what forms it generates, then decide if you need to upgrade. That way you're not committed until you actually need the premium features.

I actually faced this same decision last year and went with Deluxe for my 1099-B stock sales. Worked perfectly fine! The key is understanding what you're actually paying extra for with Premier. From my research, Premier mainly gives you additional guidance features, live tax advice, and support for more complex investment scenarios like rental properties or business income. But the actual forms needed for basic stock sales (Schedule D and Form 8949) are included in Deluxe. My advice: if your stock transactions are straightforward - just buying/selling regular stocks or ETFs from major brokerages with proper cost basis reporting - then Deluxe should handle everything you need. I saved the $30 and had zero issues. The nice thing is TurboTax lets you start your return and see exactly which forms you'll need before you commit to paying. If you run into any limitations with Deluxe, you can upgrade and just pay the difference. So there's really no downside to starting with the cheaper option and upgrading only if necessary.

I've been using TurboTax for my investment income for about 5 years now, and I can confirm that Deluxe absolutely handles 1099-B stock sales without any issues. The main thing to understand is that both Deluxe and Premier include the same core tax forms - Schedule D and Form 8949 - which are what you actually need for reporting stock transactions. Premier is really targeting people with more complex situations like rental properties, business income, or those who want extra hand-holding with investment guidance. But if you're just dealing with regular stock sales from a major brokerage (Schwab, Fidelity, Vanguard, etc.), Deluxe has everything you need. I made the switch from Premier to Deluxe three years ago specifically to save money and haven't had any problems. The import process works the same way, the calculations are identical, and you get the same accurate results. The $30 savings adds up over time too! My suggestion would be to start with Deluxe this year and see how it goes. If you somehow run into limitations (which I doubt you will), you can always upgrade mid-process and TurboTax will just charge you the difference.