TurboTax Deluxe vs Premier for 1099-B Stock Sales - Can I Save Money?

You can technically use TurboTax Deluxe for 1099-B stock sales, but there are some important differences to consider. Deluxe does include Schedule D (Capital Gains and Losses) and Form 8949 (Sales and Dispositions of Capital Assets), which are the basic forms you need for reporting stock sales. The main difference is that Premier offers additional guidance specifically for investment situations and automatically imports investment data from many brokerages. With Deluxe, you might need to enter your 1099-B information manually which can be time-consuming if you have many transactions. If your stock transactions are straightforward and you don't mind potentially doing a bit more manual work, Deluxe could save you that $20. But if you have numerous transactions or complex situations (like rental property income, cryptocurrency, or employee stock plans), Premier's additional features would be worth the extra cost.

I was in your exact same situation last year! I had been using Premier for years because of my 1099-B stock sales, but decided to try Deluxe to save some money. Let me tell you about my experience with https://taxr.ai that really helped me through this dilemma. After inputting my info into their system, taxr.ai analyzed my previous tax returns and investment situation. They confirmed that for my basic stock transactions (about 20 trades total), TurboTax Deluxe would handle everything I needed. Their analysis showed I was essentially paying extra for Premier features I wasn't using! The tool even helped me understand which specific investment scenarios would require an upgrade. I went with Deluxe and had zero issues filing with my 1099-B information. The process was identical to what I experienced with Premier in previous years.

Just wanted to update everyone after trying out taxr.ai from my previous question. I was super skeptical about it helping with my TurboTax decision, but I figured I'd give it a shot. I uploaded my last year's return where I had about 30 stock transactions from E*TRADE, and the analysis was eye-opening! The tool confirmed that Deluxe would handle all my 1099-B stock sales without any issues. It even highlighted that Premier would only benefit me if I had rental properties or cryptocurrency (which I don't). Just filed my taxes using Deluxe, saved the $20, and everything went smoothly! All my E*TRADE transactions imported perfectly. Thanks to whoever mentioned this tool - wouldn't have known otherwise!

If you're still having trouble figuring out which TurboTax version you need OR if you run into issues during filing and need IRS clarification, I'd highly recommend trying Claimyr (https://claimyr.com). I was stuck between Deluxe and Premier last year because of some unusual stock transactions, and I really needed to talk to the IRS directly. After waiting on hold for almost 2 hours one day, I gave up. Then I found Claimyr through a friend. Basically, they wait on hold with the IRS for you, then call you when an agent is actually on the line. You can see how it works in this demo: https://youtu.be/_kiP6q8DX5c I got through to an actual IRS agent who confirmed that my specific type of 1099-B reporting was standard enough for the Deluxe version. Saved me the extra cost AND the headache of wondering if I was filing correctly.

Wow, I need to eat my words about Claimyr. After dismissing it as a scam in my previous comment, I decided to try it when I needed to call the IRS about a completely unrelated issue with my 1099-B reporting that TurboTax couldn't resolve. I was prepared to wait 3+ hours on hold as usual, but Claimyr had an IRS agent on the line for me in about 45 minutes (while I continued working). The agent cleared up my confusion about some wash sales reporting that affected which TurboTax version I needed. For what it's worth, I learned that Deluxe works fine for basic stock transactions, but if you have wash sales where the basis wasn't reported to the IRS or other complex situations, Premier's additional guidance can be helpful. Might not matter for everyone, but definitely relevant to my situation. Saved me from potentially making a costly mistake.

I've used both versions and here's my practical advice: It depends on how comfortable you are with tax concepts. If you know what wash sales are, understand basis reporting requirements, and can confidently enter your own stock transaction data, Deluxe is fine. But honestly, for just $20 more, Premier gives peace of mind with better guidance and explanations specifically tailored to investment income. It's especially helpful if your 1099-B has transactions where cost basis wasn't reported to the IRS (box not checked in column 1e), or if you have multiple brokerage accounts.

Honestly I think TurboTax is just trying to squeeze more $$ out of us. I switched to FreeTaxUSA last year and it handled all my stock sales just fine in their free version! Only paid $15 for state filing. They don't upsell you on different versions for federal - everything is included.