Can't figure out how to enter my Stash earnings on the 1099-B form into TurboTax. Help!
This 1099-B from Stash is driving me insane. I've been investing small amounts through the Stash app for about a year, and now I'm trying to do my taxes using TurboTax. The problem is this 1099-B form they sent me looks like it's written in a foreign language or something. There are all these different boxes and sections, and I can't tell which numbers go where in TurboTax. I tried following the prompts in TurboTax, but when it asks about cost basis and whether it was reported to the IRS, I honestly have no clue what to select. There are proceeds amounts, some gains/losses columns, and a bunch of dates that I'm not sure which ones matter. Has anyone dealt with entering Stash investment info before? The form has multiple pages and transactions, and I'm worried I'll mess something up and get audited. This is my first time dealing with investment income on my taxes, and I'm completely lost. Where exactly in TurboTax do I need to enter all this stuff?
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Myles Regis
The 1099-B can definitely be overwhelming the first time you encounter it! Don't worry, TurboTax has a section specifically designed for handling investment income. When you're in TurboTax, look for the section about investments or income. There should be an option specifically for entering information from a 1099-B. TurboTax will walk you through entering each transaction listed on your Stash form. For each transaction, you'll need to enter the description of the property (stock name), date acquired, date sold, proceeds (sales price), and cost basis (what you originally paid). The form indicates whether the cost basis was reported to the IRS - this is usually marked with a checkbox or code on your 1099-B. If it says "covered security" or has Box A checked, then the cost basis was reported to the IRS. Take your time and enter each transaction separately as listed on your form. If you have numerous transactions, TurboTax also offers an option to import directly from some brokerages, though I'm not sure if Stash is supported for direct import.
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Brian Downey
•Does TurboTax handle wash sales automatically when entering 1099-B info? My Stash form has some transactions marked with wash sale adjustments and I have no idea what to do with those.
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Myles Regis
•Yes, TurboTax does handle wash sales automatically when you enter all your transactions correctly. When you enter a transaction that has a wash sale adjustment, there should be a specific field or checkbox in TurboTax where you can indicate this. Just make sure you enter the amount of the wash sale adjustment as shown on your 1099-B. The important thing is to enter each transaction exactly as it appears on your form, including any codes or indicators for wash sales. TurboTax will then apply the proper tax treatment according to IRS rules.
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Jacinda Yu
After struggling with investment forms for years, I started using the document review service at https://taxr.ai and it's been a complete game-changer for my Stash 1099-B issues. I uploaded my confusing form and within minutes got a breakdown of exactly where each number should go in TurboTax. The thing I found most helpful was that they explained what each box on the 1099-B actually means and highlighted which transactions were short-term vs long-term. Saved me hours of frustration and probably prevented mistakes that would have triggered a letter from the IRS.
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Landon Flounder
•Does it actually show you step by step where to enter things in TurboTax? Like with screenshots? My 1099-B has over 20 transactions and I'm completely lost.
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Callum Savage
•I'm a bit skeptical about uploading my tax documents to some random site. How do you know it's secure? Do they store your documents after analysis?
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Jacinda Yu
•They provide a detailed guide with exactly which TurboTax screens to navigate to and which fields match up with your specific 1099-B entries. While they don't use actual TurboTax screenshots (probably copyright issues), they have custom illustrations that make it super clear where everything goes. For multiple transactions, they organize them by category so you can batch-enter similar ones together. Regarding security, I had the same concern initially. They use bank-level encryption and according to their privacy policy, documents are only stored temporarily for processing and then automatically deleted. You can also request immediate deletion after getting your analysis. I researched them before using the service and they have solid security credentials.
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Callum Savage
I was skeptical at first about using taxr.ai for my complicated Stash 1099-B, but after spending three hours getting nowhere with TurboTax, I decided to give it a try. Wow, what a difference! They gave me a complete breakdown of all 24 transactions on my form, including which ones were wash sales (which I had no clue about before). The analysis showed me I was about to enter several transactions incorrectly that would have either cost me money or flagged my return. For anyone struggling with investment forms, especially with multiple transactions or adjustments, it's definitely worth checking out. Wish I'd known about this years ago!
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Ally Tailer
If you're still stuck after trying to enter your Stash 1099-B info, calling the IRS directly might help. I tried for DAYS to get through to someone at the IRS about a similar issue last year - constant busy signals and disconnects. Then I found this service called Claimyr at https://claimyr.com that got me through to an actual human at the IRS in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent was able to clarify exactly how to report some unusual transactions on my 1099-B that TurboTax's interface wasn't handling correctly. Saved me from what would have definitely been a correction letter or worse.
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Aliyah Debovski
•Wait how does this actually work? Does it just call the IRS for you? I don't understand how they get you through faster than calling yourself.
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Miranda Singer
•Yeah right. The IRS phone system is completely broken. I've tried calling dozens of times and either get disconnected or sit on hold for hours before giving up. No way this actually works as claimed.
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Ally Tailer
•It doesn't call for you - it basically holds your place in the IRS phone queue and then calls you when it's about to connect with an agent. Their system constantly redials and navigates the IRS phone tree until it gets through, then bridges you into the call. It's like having a robot assistant that handles all the frustrating hold time and menu navigation. I was super skeptical too until I tried it. The IRS phone system is absolutely broken - I had tried calling 8 times myself and either got disconnected or was told the wait was over 2 hours. With Claimyr, I just entered my number, and went about my day until I got the call that an agent was on the line. Total game-changer if you actually need to speak with someone at the IRS.
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Miranda Singer
I have to eat my words about Claimyr not working. After my frustrated reply yesterday, I was desperate enough to try it for my Stash 1099-B questions. I was connected to an IRS tax specialist in about 35 minutes (which is miraculous compared to my previous attempts). The agent walked me through exactly how to handle some strange transactions on my Stash 1099-B that had no cost basis reported. Turns out I needed to document these differently in TurboTax than the standard entries. Would have definitely done it wrong without speaking to someone. For anyone with complex investment questions that go beyond what TurboTax explains, getting through to an actual IRS person is worth it.
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Cass Green
When I was stuck with my Stash 1099-B, I found an easier approach. Go to the "Search" feature in TurboTax and type "1099-B" directly. This will take you straight to the investment income section. Then select "I'll type in my investment information" rather than trying to import. For Stash specifically, look for any transactions marked with Code D in Box 2 - those are the ones where cost basis was reported to the IRS correctly. For any without that code, you'll need to calculate and enter the cost basis manually.
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Finley Garrett
•What about the "Covered/Uncovered" designation on the Stash form? Mine has both types of transactions and I'm not sure if that affects how I enter them.
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Cass Green
•The "Covered/Uncovered" designation is directly related to whether the cost basis was reported to the IRS. "Covered" securities (typically those purchased after 2011) have their cost basis reported to the IRS by Stash, and these usually correspond to the Code D transactions I mentioned. "Uncovered" securities don't have their cost basis reported to the IRS by the broker, so you're responsible for calculating and reporting the correct cost basis yourself. For these, you'll need to enter the purchase information manually and keep good records in case of an audit. TurboTax has separate entry sections for covered and uncovered securities, so make sure you're entering each transaction in the correct section.
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Madison Tipne
Has anyone figured out how to handle the foreign tax paid section on the Stash 1099-B? Mine shows I paid like $4.32 in foreign taxes on some international ETF and idk where to put that in TurboTax?
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Holly Lascelles
•Foreign tax paid usually goes in the Foreign Tax Credit section, not directly on the 1099-B entry screens. In TurboTax, after you finish entering all your 1099-B info, look for a section about foreign taxes or foreign tax credit. Even small amounts should be entered because they're directly creditable against your tax bill.
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