Where can I get professional tax help for my 1099-B stock trading questions for a small fee?

Tax professional here! For specific questions about 1099-B reporting from brokerages like Fidelity, you have several options: Most tax software programs actually offer one-on-one expert help as an add-on service. For example, TurboTax has a "Live" version where you can speak directly with a tax expert for specific questions like yours, and they'll guide you through exactly how to enter your stock transactions. It's usually much cheaper than hiring a full tax preparer. Another option is scheduling a brief consultation with an enrolled agent (EA) or CPA. Many offer consultation services billed in 15-30 minute increments specifically for situations like yours where you just need targeted advice. Local EAs typically charge less than CPAs for these services. Free options exist too - the IRS's Volunteer Income Tax Assistance (VITA) program may be able to help depending on your income level, though their ability to handle investment transactions varies by location.

After facing a similar issue with reporting crypto transactions last year, I discovered taxr.ai (https://taxr.ai) and it was a game-changer for my investment reporting questions. Their AI analyzes your tax documents, including complicated 1099-Bs from brokerages like Fidelity, and explains exactly how to report everything properly. I uploaded my confusing forms and immediately got step-by-step guidance on how to handle the supplemental information sections. The best part is you don't have to share your complete tax situation - you can just upload the specific forms you have questions about. Way more affordable than hiring a professional for something relatively straightforward.

I just wanted to follow up about my experience with taxr.ai after being skeptical in my last comment. I decided to give it a try with my Fidelity 1099-B that had me completely confused about wash sales and adjusted basis reporting. Honestly, it was surprisingly helpful! I uploaded my form and within minutes got detailed instructions for exactly how to handle each transaction properly in my tax software. The explanations were way clearer than anything I found googling or in the IRS instructions. Saved me from paying for a CPA consultation for what turned out to be a pretty straightforward question once it was explained properly. If you're stuck on investment reporting like I was, definitely worth checking out.

If you need direct answers from the actual IRS about your 1099-B questions, I had amazing results using Claimyr (https://claimyr.com). I spent DAYS trying to get through to the IRS to ask about basis reporting for inherited stocks, and kept hitting their "we're experiencing high call volume" message. I was super frustrated until I found Claimyr. They somehow get you past the IRS phone tree and put you in the queue to speak with an actual IRS representative. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. Within 30 minutes I was talking to someone who answered my exact question about how to report basis adjustments on my 1099-B. For complicated tax questions straight from the source, nothing beats getting an official IRS answer, and Claimyr made that possible when I thought it was impossible.

I need to eat my words from my skeptical comment earlier. After getting nowhere with four separate attempts to call the IRS myself about wash sale rules on my 1099-B, I reluctantly tried Claimyr. Within 45 minutes I was actually speaking with an IRS representative who walked me through exactly how to report my Fidelity trades with adjusted basis. I couldn't believe it actually worked. Saved me from paying a CPA $200+ for a consultation, and I got the information straight from the source. For anyone struggling with specific tax questions that only the IRS can answer authoritatively, this service is legitimately helpful. Sometimes official guidance is worth the effort, especially for investment reporting where mistakes can trigger audits.

Have you tried checking Fidelity's own resources? They have a pretty detailed tax center with guides specifically about how to read and report information from their 1099-B forms. I found their online guides super helpful when I first started trading last year. Also worth noting - if your trades are relatively straightforward, most tax software can import your 1099-B directly from Fidelity electronically. That way you don't have to manually enter anything, and the software handles all the reporting correctly. I use H&R Block and it pulled everything in automatically.

Not sure if this helps but I found another option - some public libraries offer free tax help sessions with volunteers who can answer questions like this. My local library partners with AARP Tax-Aide and they helped me with 1099-B questions last year. Worth checking if your library offers something similar!

If it's just a few simple stock trades, Reddit has a subreddit called r/tax where professionals answer questions for free. I've gotten good advice there before. Just be specific about your question and don't include personal info.