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Best tax self-service platform for hassle-free import of TD Ameritrade 1099b?


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Last year I used H&R Block to file my taxes online. Importing the 1099b with my trade history worked effortlessly. This year H&R Block somehow screwed up the importing functionality, so that I'm having to manually go through each trade to select "various" if it's not one acquisition date, as well as manually select "basis already reported to IRS" for every trade. Even after going to all this trouble I'm not sure if the capital gain will calculate and reflect correctly on the actual tax return form when I go to file. Am unhappy that they hid the broken functionality by not letting me preview the return until I'd already paid, as it was only then that I had a way of seeing the imported data was wrong. I will never use them again after this.

Can anyone recommend an affordable tax prep self-service site/platform that always reliably works for importing the 1099b form?

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I always use H&R Block to file my tax return. I've never had a problem with this platform, so I don't even know what to advise you. You can try https://www.humaninvesting.com/financial-planning, which will allow you to plan the income you receive, distribute it properly and always stay in the black. Having a lot of capital, you may be having trouble with cash flow. Experienced business people use various financial planning tools to always stay in the black. A man who always develops and improves his knowledge and skills achieves high results.
TurboTax is considered the best tax software out there. I've been filing all my taxes there for some time, and I don't have any problems. Yes, I know these problems are related to H&R Block, and I haven't tried to use them. Besides that, I found a pay stub generator that helped me create my paystub in 2 minutes, and I also entered all my financial data there. This helps me a lot to be financially educated and to monitor my income and expenses carefully. This makes me much more reasonable, and I recommend you consider this step. It's really useful.
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Hi there dear folks. I heard of TaxSlayer, but I've never actually tried it. I think you could contact greedyrates.ca on your issue. I have a friend there, so he's a great specialist, actually. Btw, he's also responsible for managing my expenses and income. He helps me with my investments, so I recommend you contact this company. I hope I've helped you. Anyway, keep us updated on your issue. Share the companies or services you may have found while solving your problem.
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That's seriously frustrating about H&R Block. It ****s when something that used to work seamlessly suddenly becomes a hot mess. I totally feel you on wanting to switch it up for next year.
Have you checked out successionresource.com? They have a bunch of resources on the best tax self-service platforms, including ones that specifically mention the import of TD Ameritrade 1099b. I personally haven't used any of them yet, but it might be worth doing some research and seeing which one works best for you.
Another option could be to hit up some personal finance subreddits or Facebook groups to see what other people are using.
I used HRBlock this year and my information did not import correctly. I had to delete the imported info, and add it manually (using grouped transactions).
I can't help you if you're trading stocks or ETFs. However, if you're trading futures you're only required to enter one number. Transaction-level details aren't required. I've used TurboTax in the past, but would recommend that if your gains are more than a few thousand dollars you consult a tax pro. For $150 they can often find very good ways of helping you avoid way more than the $150 fee.

That said, TurboTax does import 1099b documents just fine with one exception - not for futures. But again, it's just a single number entry, so not a big deal. They do hide the 1099b import function in a different place each year though, so you'll just have to search in their help box to find it.
For me, H&R was a dumpster fire last year. I did the best I could with their web interface and paid the extra for their people to review/correct what I couldn't get working.

My return got tossed around to 5-6 different preparers and eventually landed on someone's desk who tried to finish it 2-3 times and I kept kicking it back because large chunks of information were missing. I mean it was obvious stuff that didn't need a calculator. I'm still not confident my return was prepared correctly. It was a fairly complex return with K-1 income, several thousand stock trades, and a QEF-elected PFIC.

This year I'm using the desktop Turbotax and it brought difficulties of its own. I legit bought and paid for the software but ran out of activations, having to repeatedly retype the activation code. I finally gave up and cracked it like a filthy pirate. Got a 90-day extension because I'm waiting on a K-3 from one of my stoopid MLPs.

The 1256 contracts should be simple but TurboTax's wording is unclear vs the verbiage on my 1099 and I plan to pay extra for someone at TurboTax to review my work. And I'll have to manually attach the PFIC form (8621?) since their platform doesn't support that kind of subversive goings-on.

I guess next year I'll break down and hire someone.

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