Best places to ask questions about 1099-B from Fidelity for a small fee?

Thanks for the quick response! I've tried using the guided section in tax software but got stuck with some of the wash sale information on the supplemental pages. Do you know if the consultation services would allow me to show them the actual form to get specific guidance? I'm worried about misreporting something and getting flagged.

Yes, consultation services absolutely allow you to show your documents - that's actually the best way to get accurate advice. Most tax pros offer virtual consultations where you can screen-share or email your forms beforehand so they can see exactly what you're working with. This makes it much easier for them to provide specific guidance on wash sales or other complex reporting situations on your 1099-B. For Fidelity specifically, they organize their supplemental information in a particular way, and someone who's familiar with their forms can quickly help you understand what goes where. Just make sure to tell them upfront that you only need help with this specific issue and not full tax preparation.

Does it actually work with the Fidelity supplemental information pages? Those are the ones causing me the most headaches - especially figuring out which transactions need special treatment. Can it handle multiple stock trades or just basic ones?

I'm a bit skeptical about uploading my financial documents to some random website. How secure is this service and who's behind it? Is it actual tax professionals reviewing the documents or just some AI system making guesses?

The service absolutely works with Fidelity's supplemental pages - that's exactly what I used it for. It can handle dozens or even hundreds of trades and will identify all the special cases like wash sales, short vs long term gains, and even missing basis information. It's particularly good at explaining which line items need to be reported separately versus which can be summarized. Regarding security, they use bank-level encryption and their privacy policy prohibits using your data for anything other than providing the service. It's not just an AI making guesses - they have tax professionals who developed the system based on IRS regulations. The analysis is automated but based on the same rules a CPA would use to interpret your forms.

Wait, how does this actually work? Does it just keep calling the IRS for you? I thought the whole problem was that no one can get through to them in the first place.

This sounds like a complete scam. The IRS phone system is notoriously impossible to navigate. I highly doubt some service can magically get you through when millions of people can't reach them every tax season. Sounds like you're selling something here.

It actually uses technology to navigate the IRS phone system and secures your place in line. Instead of you personally waiting on hold for hours, their system does the waiting, monitoring the call until it detects a live agent, then immediately connects you. It's not "magic" - just smart use of technology to solve the hold time problem. I was skeptical too before trying it, but it's legitimate. They don't do anything you couldn't theoretically do yourself if you had unlimited time and patience to keep calling and waiting on hold. They're just automating that frustrating process. The IRS agents don't know or care how you got through - they just answer your questions once you're connected.

That's a great idea I hadn't thought of! Have you actually gotten detailed help from them before on how to report specific transactions? I'll definitely give them a call tomorrow if that's the case.

I've gotten basic guidance from them before, but it can be hit or miss depending on who you talk to. Their customer service can usually help clarify what specific codes or entries on your form mean. What they typically won't do is give specific tax advice about how to report things on your return - they'll explain their form but stop short of telling you exactly what to enter on your tax forms. Still worth calling though, as they can often clear up confusion about what certain transactions or adjustments on their statements represent.

I've had mixed results with Reddit. Sometimes you get amazing detailed answers from actual tax pros, and other times you get conflicting advice that leaves you more confused. The challenge is knowing which advice to trust when you get multiple different answers.