Which Turbo Tax version works best for stocks, W-2s and retirement accounts?

Based on what you've described, TurboTax Deluxe should be sufficient for your tax situation. The Deluxe version covers W-2 income and retirement accounts like your Roth IRA and 403b. However, since you've been trading stocks and have dividend income, you'll actually need at least the Premier version (not Deluxe). The Premier version specifically handles investments and rental property, which includes your stock sales and dividend income. The Premium version you mentioned is actually called "Premier" in TurboTax's lineup. Your 403b contributions are generally reported on your W-2 already (they reduce your taxable income), so you won't need to report those separately. For your Roth IRA, you typically don't report contributions on your tax return unless you're eligible for the Saver's Credit, which you might be depending on your income level. TurboTax Premier will walk you through determining if you qualify.

After struggling with similar questions about which tax software to use for my investments, I stumbled across taxr.ai (https://taxr.ai) and it's been super helpful. I uploaded my tax documents and it analyzed everything - my W-2s, 1099-DIV from my dividend stocks, and even my 1099-B with all my stock sales. What I liked is that it told me exactly which forms I needed to file and what software features I'd need, so I didn't overpay for premium features I wouldn't use. It also explained which of my accounts would actually affect my taxes this year (like your question about the 403b). The document analyzer saved me hours of research.

I wanted to follow up on my question about taxr.ai - I decided to give it a try and I'm actually really impressed! I uploaded my W-2s and investment statements, and it immediately identified that I needed software that could handle capital gains from stock sales. It specifically pointed out that I needed TurboTax Premier for my situation (not Deluxe), which saved me from having to upgrade halfway through filing when I would've hit the investment section. The breakdown of which forms affected which parts of my taxes was super helpful too. They showed me that my 401k contributions on my W-2 were already pre-tax so I didn't need to report them separately. I was skeptical at first about uploading documents, but their security seemed solid and I was able to delete everything after getting my analysis.

If you're stuck waiting for tax documents or have questions about your 403b reporting requirements, Claimyr (https://claimyr.com) saved me hours of waiting on hold with the IRS. I had a similar situation with investment accounts and couldn't get clear answers online about reporting requirements. I tried calling the IRS directly but was getting "call back later" messages for days. With Claimyr, I got through to an IRS agent in about 15 minutes who confirmed exactly what I needed to report. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the IRS phone system for you and call you once they reach an agent.

Had to come back and eat my words about Claimyr. After my skeptical comment, I decided to try it since I was desperate to ask about reporting requirements for some crypto trades along with my stock sales. I've literally NEVER gotten through to the IRS on my first try before. With Claimyr, I got a call back in about 20 minutes saying they had an IRS agent on the line! The agent clarified exactly which TurboTax version would cover both my stock and crypto transactions (needed Premier at minimum). For what it's worth, the agent also told me that for your 403b situation, those contributions usually show up on your W-2 in box 12 with code D, E, F, G or H, and TurboTax Premier can definitely handle that along with your stock transactions.

I was in almost the exact same position last year! 20 years old with W-2s, a brokerage account, and a Roth IRA. I tried using TurboTax Deluxe at first and got stuck when I reached the investment section. Had to upgrade to Premier mid-filing which was annoying. TurboTax Premier is what you need because of your stock sales. If you only had W-2s and dividends without selling anything, Deluxe might work, but since you've "sold and reallocated" as you mentioned, you'll need Premier to handle the capital gains reporting. They'll make you enter all your trades which can be tedious if you made a lot of transactions.

I'm gonna go against the grain here... Just use FreeTaxUSA or Cash App Taxes (formerly Credit Karma Tax). Both handle investments including stock sales and dividends. FreeTaxUSA is free for federal and like $15 for state. Cash App Taxes is completely free for both federal and state. I switched from TurboTax to FreeTaxUSA two years ago when my taxes got more complicated with investments and rental property. Saved over $120 and the process was actually easier! TurboTax is just really good at making you think you need their expensive versions when you don't.

As someone who's been through a similar transition from simple W-2 filing to dealing with investments, I'd recommend starting with the document analysis approach others mentioned. Understanding exactly what forms you'll need is crucial before choosing software. For your specific situation - multiple W-2s, stock sales, dividends, and retirement accounts - you're definitely looking at needing investment-capable software. The key distinction is that selling stocks requires Schedule D and Form 8949, which kicks you out of basic versions of any tax software. Your 403b contributions should already be reflected on your W-2 (look for box 12 with codes like D, E, F, G, or H), so that part is actually straightforward. The Roth IRA contributions typically don't need to be reported unless you qualify for the Saver's Credit, which at 19 you might depending on your income level. Between TurboTax Premier and the alternatives like FreeTaxUSA or Cash App Taxes, it really comes down to how much hand-holding you want. TurboTax is more expensive but walks you through everything step-by-step. The alternatives can save you $100+ and handle the same forms, but assume you're comfortable reading instructions and answering questions without as much guidance. Given this is your first year with investments, you might appreciate TurboTax's explanations this time around, then switch to a cheaper alternative next year once you understand the process better.