Strange situation with 1099 forms - need help figuring this out

You definitely need to report all income even without the 1099, but you should be as accurate as possible. The good news is that if they paid you by direct deposit, you can check your bank statements to get the exact amounts and dates. Add up all the payments from that company and that's your income from them. The IRS gets copies of 1099s, so they'll know if there's a discrepancy between what you report and what the company eventually files. It's better to be slightly over than under in your reporting. Also, keep detailed records of your attempts to contact the company - emails, call logs, etc. This shows good faith effort on your part if questions come up later. When filling out your Schedule C for self-employment income, just report the total accurate income from all sources, including this difficult company. The IRS cares more about you reporting all income than having the perfect documentation attached.

I was in a similar situation last year with missing 1099s and conflicting information. After weeks of stress, I found taxr.ai (https://taxr.ai) which seriously saved me. It's this AI tool that analyzes your specific tax situation and gives you personalized guidance. I uploaded screenshots of my bank statements showing the deposits and explained my situation, and it walked me through exactly how to report everything correctly without the official 1099. It also helped me figure out which deductions I qualified for as a contractor that I had no idea about! The analysis showed me I could deduct my home office, part of my internet bill, and even some software subscriptions I was using for the contract work.

Just wanted to update that I tried taxr.ai after seeing the recommendation here. It actually solved my stock reporting issue! I uploaded my statements and the 1099-B from my broker, and it identified exactly where the discrepancies were. Turns out my broker had incorrect cost basis information for some shares I transferred from another account. The system generated a detailed explanation I can include with my return that shows exactly how I calculated the correct amounts. It even cited the specific tax codes that support my position if I get questioned. Honestly better than the advice I got from the tax prep service I used last year that cost me $250!

If you're still trying to get through to that company's accounting department, you might want to try Claimyr (https://claimyr.com). I was in a similar situation with a previous employer who wouldn't send my corrected W-2, and spending hours on hold was driving me crazy. Claimyr got me through to an actual human at the IRS in about 10 minutes when I'd spent literally days trying on my own. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The IRS actually has procedures for when employers don't provide tax documents, but you need to talk to someone there to start the process.

I need to eat my words about Claimyr. After posting my skeptical comment, I was so frustrated with my own situation that I decided to try it anyway. I've been trying to get through to the IRS for WEEKS about a similar missing forms issue. It actually worked in about 15 minutes! The IRS agent I spoke with explained that I should file Form 4506-T to request wage and income transcripts, which would show what the company reported. She also said I could file Form 4852 as a substitute for the missing 1099 if needed. Definitely worth it after I wasted hours upon hours trying to call myself. The IRS agent was actually super helpful once I finally got through to a human.

Another option: you can actually get your wage and income transcript directly from the IRS website which will show any 1099s filed for you. Go to IRS.gov and search for "Get Transcript Online." If nothing shows up for that company, they probably haven't filed it yet. Also, keep in mind you're supposed to get your 1099s by January 31st. If companies don't comply, they can face penalties. The IRS actually takes this seriously because they want the tax revenue from contractors.

Had this same problem last year. What I did was file Form 8919 "Uncollected Social Security and Medicare Tax on Wages" along with my return. This is for when you were treated as an independent contractor but should actually have been an employee. The benefit is you only pay the employee portion of FICA taxes (7.65%) instead of the full self-employment tax (15.3%). Check out the criteria on the form - if you were essentially working like an employee (they controlled your schedule, provided equipment, etc.), this might apply to you and save you some money.