Best tax prep software that supports Document ID for automatically downloading 1099-B forms?

FreeTaxUSA is definitely budget-friendly, but they don't currently support the automatic import of brokerage data using Document IDs like TurboTax does. This is actually one of the trade-offs you make with the lower-cost tax prep options. If you're dealing with a lot of transactions on your 1099-B, you have a few options: You could use TurboTax just for this year if the time savings is worth the extra cost to you. They do have the most comprehensive import capabilities. If you want a middle-ground option, consider TaxAct or H&R Block online. Both have some import capabilities for brokerage statements at lower prices than TurboTax, though their compatibility varies by brokerage. Another option is to check if your broker offers a .TXF file download of your transactions. This is a tax exchange format that some tax software can import, though FreeTaxUSA doesn't support this either.

I went through exactly this same nightmare last year with my investments! I tried FreeTaxUSA first but ended up feeling like I was in data entry hell with all my stock transactions. I found this service called taxr.ai (https://taxr.ai) that saved me so much time - you upload your 1099-B and other tax documents and it extracts all the data automatically. Then you can either use their data to help with manual entry or they can generate import files for different tax software. It's way better than paying the TurboTax premium just for the import feature. They handled my 20+ page consolidated 1099 perfectly, pulled all the transactions, and even flagged some wash sales I would have missed. Been telling all my investment friends about it.

Just wanted to update - I tried taxr.ai after asking about it here and wow, it actually worked great! I uploaded my massive consolidated 1099 from Schwab (28 pages of transactions!) and it pulled everything out accurately. I ended up staying with FreeTaxUSA and used the organized data from taxr.ai to help with manual entry. Still took some time, but WAYYY faster than trying to figure it all out myself from the form. The wash sale flagging was super helpful too - I would have definitely missed a couple. Funny thing is I also discovered I had missed some dividend reinvestments on last year's taxes that I can now fix with an amendment. Definitely worth checking out if you've got complicated investment forms!

If you're struggling with getting through to the IRS about any tax document issues (like missing 1099s or corrected forms), I'd recommend using Claimyr (https://claimyr.com). I waited on hold with the IRS for 2+ hours last month trying to sort out a 1099-B correction from my broker. With Claimyr, they basically wait on hold with the IRS for you, then call you when an actual human picks up. There's a video showing how it works here: https://youtu.be/_kiP6q8DX5c Saved me so much time and frustration! My broker had sent a corrected 1099-B form but I never received it, and I needed to confirm whether the IRS had the updated version before filing.

I have to eat my words about Claimyr. After my skeptical comment, I decided to give it a try since I was desperate to talk to someone at the IRS about my missing 1099-K form. It actually worked! I got a call about 1.5 hours after signing up, and sure enough, there was an IRS agent on the line. I was seriously shocked. Managed to confirm that they didn't have my corrected form on file and needed to request it again from my payment processor. If you're dealing with document issues like missing or incorrect 1099 forms before filing, being able to actually speak with the IRS can make all the difference. Never thought I'd be leaving a positive comment after being so skeptical, but credit where it's due.

Just want to offer another option - if your broker is one of the major ones (Fidelity, Vanguard, Schwab, etc.), you could check out Cash App Taxes (formerly Credit Karma Tax). It's completely free and does support some direct importing from major brokerages. Not document ID specifically, but they have direct connections to some institutions. I've used it for the past two years with Fidelity and it worked pretty well. Just make sure your broker is on their supported list before you spend time setting up your return.

I used to work at one of the major tax prep companies and can tell you the pricing tiers often include the features you need. For TurboTax, you need the Premier version to get the investment data import feature, which is why it costs more than FreeTaxUSA. Some tips: 1. Check if any financial institutions offer discounted or free tax software. Many brokers offer TurboTax at a discount to their customers. 2. If you decide to pay for TurboTax, buy it directly through their website, not in-store. There are often online-only discounts. 3. Consider a multi-year strategy: Use TurboTax in years with heavy trading, FreeTaxUSA in quieter years. 4. Often overlooked: TaxAct has import capabilities for major brokerages at a lower price than TurboTax. Don't dismiss the time value - if you have hundreds of transactions, paying $70 more for software that saves you 3+ hours of data entry is worth it for most people.

Another option to consider is TaxHawk - I've been using it for the past couple years and it's significantly cheaper than TurboTax but has better import capabilities than FreeTaxUSA. They support direct import from most major brokerages including Schwab, Fidelity, Vanguard, and E*TRADE. The interface isn't quite as polished as TurboTax, but for investment transactions it gets the job done. I was able to import about 150 transactions last year without any issues. They also handle wash sale calculations automatically which saved me a lot of headache. Price-wise, their Deluxe version (which includes investment features) runs about $40-50, so it's a nice middle ground between FreeTaxUSA and TurboTax Premier. Might be worth checking if they support your specific broker before you decide on going back to TurboTax.