Need help entering Stash 1099-B earnings into TurboTax - form is confusing and hard to read

I'm pulling my hair out trying to figure out how to enter my Stash investments into TurboTax this year. I got my 1099-B from Stash and honestly have no idea what I'm looking at or where to put any of this information. The form is so confusing and tiny - there are all these boxes and numbers and I can't tell what goes where in TurboTax. I've never had investments before this year so this is all new to me. I only put like $600 into Stash throughout 2024 and made a few small trades, but now I have this complicated 1099-B form. TurboTax keeps asking me about "covered" vs "non-covered" transactions and something about "basis reported to IRS" and I'm completely lost. Has anyone dealt with Stash and TurboTax before? Where exactly do I enter all this stuff? Do I need to go line by line or is there an easier way? My eyes are crossing trying to match up these tiny numbers on the form with the fields in TurboTax.

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19 comments

Maya Lewis

•8M

You're dealing with a common issue many first-time investors face! The 1099-B can definitely be intimidating, but TurboTax should be able to handle this fairly well. First, when you're in TurboTax, go to the "Federal" section, then look for "Income & Expenses" and select "Investment Income." There should be an option specifically for entering 1099-B information. For Stash specifically, they usually provide transactions that are "covered," which means the cost basis (what you paid) has been reported to the IRS. This makes your job easier. When TurboTax asks about covered vs. non-covered, select "covered" for most Stash transactions. The form might look complicated, but focus on these key pieces: the description of property (stock name), date acquired, date sold, proceeds (what you sold it for), and cost basis (what you paid). These are the essential items TurboTax needs to calculate your gains or losses correctly.

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Maya Lewis

•8M

You should enter each individual transaction for the most accurate return. While it's tempting to just use the summary, the IRS receives details on each transaction, and entering them individually ensures everything matches their records. TurboTax does have an import feature that might work with Stash to save you from manual entry. Look for an "import" button when you're in the investment section. If that doesn't work, some people take photos of their forms using the TurboTax app, which can sometimes automatically read and enter the data.

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Isaac Wright

•8M

I was in the exact same boat last year trying to figure out how to enter my Stash 1099-B into TurboTax! After hours of frustration, I discovered taxr.ai (https://taxr.ai) and it completely changed my tax filing experience. I uploaded my Stash 1099-B document to the site, and it analyzed all those confusing transactions and explained exactly what I needed to enter in TurboTax. It even highlighted which transactions were short-term vs long-term capital gains and pointed out a few wash sales I had no idea about. The best part was that it translated all that tax jargon into plain English and gave me step-by-step guidance for TurboTax's specific screens. Saved me from what would have been hours of confusion!

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Isaac Wright

•8M

It handles all individual transactions, including those small dividend reinvestments. The tool actually categorizes everything by transaction type, so you can see all your dividend reinvestments grouped together which makes it much easier to understand what's happening with your investments. Regarding security, I had the same concern initially. They use bank-level encryption and don't store your documents permanently after analysis. As for accuracy, they explain every calculation they make and why, which actually helped me understand what I was filing rather than just blindly entering numbers. If you're worried about an audit, having this detailed breakdown of how you arrived at your numbers is actually really helpful documentation to keep.

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Lucy Taylor

•8M

Just wanted to follow up about my experience with taxr.ai after someone recommended it here. I was really struggling with my Stash 1099-B that had over 30 transactions from dividend reinvestments. I uploaded my form and was honestly blown away by how it broke everything down. It separated my short-term and long-term capital gains, flagged a few wash sales I had (which I didn't even know was a thing), and gave me clear instructions for each TurboTax screen. The explanation of covered vs. non-covered transactions finally made sense to me! I was able to enter everything correctly in about 20 minutes when I was previously spending hours trying to figure it out. Definitely using this again next year for all my investment forms.

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KhalilStar

•8M

After spending 3 days trying to reach someone at the IRS to ask about reporting Stash transactions correctly (kept getting disconnected or 2+ hour wait times), I finally tried Claimyr (https://claimyr.com) after seeing someone mention it on another thread. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was connected to an actual IRS agent in about 15 minutes! The agent walked me through exactly how to report my Stash 1099-B transactions correctly and explained that I needed to report each transaction individually rather than summary totals. She also confirmed that wash sales were being calculated correctly by Stash. I was honestly shocked it worked because I'd been trying to get through to someone for days. Definitely worth it for the peace of mind knowing I filed everything correctly.

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KhalilStar

•8M

It basically handles the waiting for you. The service actually calls the IRS and navigates through all those annoying menu options, then waits in the queue. When they finally reach a human agent, you get a call so you can talk directly to the IRS person. It's not skipping the line - it's just having someone else do the waiting for you. I was super skeptical too at first. I'd already spent hours trying to get through myself and kept getting disconnected after waiting forever. I figured it was worth trying since I was desperate for answers about reporting these Stash transactions correctly. It honestly worked exactly as advertised - I got a call when an actual IRS agent was on the line, ready to help with my questions.

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Kaiya Rivera

•8M

Well I have to eat my words about Claimyr. After posting my skeptical comment last week, I decided to try it as a last resort because I was still confused about my Stash 1099-B reporting. I was absolutely shocked when I got a call back with an actual IRS agent on the line about 20 minutes later. The agent was super helpful and explained that my Stash transactions needed to be entered individually, not as summary totals. She also confirmed how to handle my wash sales correctly in TurboTax. After weeks of frustration trying to call myself and getting nowhere, this was honestly a game-changer. Filed my taxes correctly yesterday and actually feel confident that I did it right instead of just guessing and hoping for the best.

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Katherine Ziminski

•8M

For what it's worth, I just uploaded my Stash PDF directly to TurboTax and it auto-imported everything! I didn't have to manually enter anything at all. Look for the "Import" button at the top of the investment income section when you're entering 1099-B info. If your document doesn't import correctly (mine didn't the first time), try downloading a fresh PDF from Stash and make sure you're saving it directly rather than taking a screenshot. That fixed it for me.

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Katherine Ziminski

•8M

I did actually have that happen on my first attempt! The problem was that my PDF had two pages, and TurboTax only imported the first page. I had to combine all the Stash PDF pages into a single document and then it worked perfectly. As for the wash sales, yes - TurboTax identified them correctly after importing. I double-checked a few transactions manually and everything matched up with what was on my 1099-B. Just make sure when you're reviewing that the "Box A" checkbox is marked for covered securities, since that's what most Stash investments are.

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