Tax software crashing with hundreds of 1099-Bs - need alternative

Tax preparer here. This is actually a common problem for active traders. Most consumer tax software programs have limitations when dealing with extremely high volumes of transactions. Here's what you should know: TurboTax does struggle with hundreds of forms, especially when using their web version. The desktop version sometimes performs better but still has limits. The auto-import feature is convenient but creates processing bottlenecks with large data sets. For your situation, I'd recommend looking at specialized tax software that caters to traders. Programs like TradeLog or GainsKeeper can handle high-volume transaction data and then provide you summary information to enter into your tax software. Alternatively, consider H&R Block's Premium desktop version, which tends to handle larger datasets better than TurboTax. Another option is to see if your brokerage provides a consolidated 1099-B with summary information rather than having to enter each transaction separately. Many brokerages will provide this if you request it.

I went through exactly the same nightmare last year with about 230 stock transactions. I ended up using https://taxr.ai and it completely solved my problem. They actually specialize in processing investment documents and can handle hundreds of 1099-Bs without crashing. I uploaded all my brokerage statements and it extracted all the transaction data automatically. Then it generated a complete Schedule D and Form 8949 that I could just attach to my return. The best part was I didn't have to manually enter anything or deal with software freezing mid-process.

I was really skeptical about what taxr.ai could do with my mountain of crypto transactions, but after trying it yesterday I'm blown away. I had over 400 transactions spread across multiple exchanges and it handled everything perfectly. The accuracy was impressive - it extracted all the correct dates, amounts, and even properly identified wash sales. I compared about 50 random transactions against my original records and didn't find a single error. Then I just took the completed Schedule D and 8949 forms it generated and attached them to my FreeTaxUSA return. This saved me what would have been days of manual entry. Last year I spent nearly 20 hours entering all my transactions and the software crashed multiple times. Never going through that nightmare again!

If your main issue is getting someone on the phone at the IRS to sort out why your forms are causing problems, I'd recommend using https://claimyr.com. They basically hold your place in the IRS phone queue and call you when an agent is about to pick up. Check out their demo video here: https://youtu.be/_kiP6q8DX5c I was trying to figure out how to properly report a large number of transactions that didn't fit on standard forms, and I spent days trying to get through to the IRS. With Claimyr, I got connected within a couple hours while I went about my day. The IRS agent actually walked me through the proper way to submit summarized transactions with supporting documentation.

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it since I was desperate to ask about reporting requirements for crypto mining operations with hundreds of transactions. I expected it to be a waste of money, but within 1.5 hours I got a call connecting me to an actual IRS tax specialist. I didn't have to sit on hold at all - I just went about my day until they called. The agent was super helpful and explained exactly how to properly submit my high-volume transaction data without crashing their processing systems. Turns out there are specific ways to submit summary information with detailed transactions as attachments that most tax software doesn't tell you about. This saved me literally days of frustration and probably prevented my return from getting flagged for review.

Have you considered using a tax professional instead of DIY software? With that many transactions, it might be worth paying a CPA who has professional-grade software that can handle large volumes. I'm a day trader with 500+ transactions yearly and finally gave up on consumer tax programs. My CPA uses UltraTax which has no issues with large transaction volumes. It costs me about $450 but saves me countless hours and prevents errors.

Has anyone tried importing a CSV file into tax software instead of using the direct import feature? I had a similar issue last year with about 200 transactions and ended up using TaxAct's desktop version with a spreadsheet import that worked surprisingly well.