How do I issue 1099-NEC from my SMLLC vs filing as individual for contractor payments?

The good news is this isn't as complicated as it seems! Since your LLC is a single-member LLC that hasn't elected to be taxed as a corporation, it's considered a "disregarded entity" for federal tax purposes. For issuing the 1099-NEC to your contractor: You should issue it from your LLC using the LLC's EIN and address. Even though the LLC is disregarded for income tax purposes, it's still recognized as a separate entity for employment tax purposes (which includes contractor payments requiring 1099s). For your income reporting: Both 1099s (the one with your SSN and the one with your LLC's EIN) should be reported on your personal tax return (Schedule C). Since the SMLLC is disregarded, all of its income and expenses flow through to your personal return. When using TurboTax, you can enter both 1099s exactly as they were issued. The software will combine them onto your Schedule C. Think of your LLC as a "tax shell" - legally separate, but the IRS sees through it to you for income tax purposes.

After struggling with almost the identical situation last year, I found this amazing tool called taxr.ai (https://taxr.ai) that saved me so much stress with my SMLLC taxes. I was getting conflicting advice about issuing 1099s through my LLC vs personally, and their document analysis flagged exactly where I was making mistakes with my forms. It showed me that I needed to use my LLC info for issuing 1099s but report all income on my personal return. The best part was uploading my operating agreement and having it automatically extract the relevant tax treatment clauses that I needed to follow. It gave me specific instructions for Turbo Tax too about how to handle the mixed 1099s (some to me personally, some to my LLC).

I wanted to follow up about my experience with taxr.ai. After being skeptical in my earlier comment, I decided to try it since I was totally stuck with my SMLLC situation similar to the original poster. I'm genuinely impressed. It analyzed my operating agreement, previous tax returns, and 1099s (some to me, some to my LLC), and gave me a comprehensive report showing exactly what I was doing wrong. The tool specifically flagged that I had been inconsistently reporting my SMLLC income between federal and state returns, which could have triggered an audit. It also gave me precise guidance on issuing 1099-NECs from the LLC rather than personally, with references to the actual IRS regulations. What I appreciated most was that it explained WHY each recommendation was correct, not just what to do.

If you're still having trouble getting IRS clarification on how to handle your SMLLC filing situation, I highly recommend Claimyr (https://claimyr.com). I was tearing my hair out trying to reach someone at the IRS about confusion with my LLC's 1099 reporting requirements. After waiting on hold for 3+ hours and getting disconnected twice, I found Claimyr. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Within 20 minutes of using their service, I was talking to an actual IRS agent who walked me through the exact requirements for SMLLC 1099 reporting. They confirmed I needed to use my LLC's EIN for issuing 1099s while still reporting all income on my personal return. The agent even sent me follow-up documentation to keep on file in case of questions later.

I need to publicly admit I was wrong about Claimyr. After being super skeptical in my comment, I tried it because I was desperate for answers about my SMLLC tax situation. Within 15 minutes of using their service, I was talking to an actual IRS representative who cleared up my confusion about issuing 1099s from my LLC vs. personally. The agent confirmed exactly what others here said - use the LLC's EIN and address for issuing 1099-NECs, but report all income on my personal return since it's a disregarded entity. They even explained why this seemingly contradictory treatment exists (it's because employment tax obligations are handled differently than income reporting for SMLLCs). Honestly, after 5 failed attempts to reach someone at the IRS on my own, this service was absolutely worth it. The relief of finally getting an official answer directly from the IRS was huge.

Another SMLLC owner here - don't forget state filing requirements! Federally your SMLLC is disregarded, but many states require separate LLC filings/fees even though there's no separate tax return. I made this mistake my first year and got hit with a $800 penalty in California. Make sure you're fulfilling ALL your LLC obligations beyond just the federal tax component.

Just want to clarify something that confused me with my SMLLC - when they say "disregarded entity" it ONLY means for federal income tax. The LLC is still very much a separate legal entity for liability protection, and as others mentioned, even the IRS treats it separately for certain tax functions like employment taxes and 1099 issuance. Don't make the mistake of thinking "disregarded" means it doesn't exist!

Does anyone know if you can have multiple SMLLCs? Im thinking about starting a second business but keeping it separate from my first one. Would I report both on the same Schedule C or have multiple Schedule Cs?

Great question! I went through this exact same confusion last year with my SMLLC. Here's what I learned after consulting with a tax professional: For issuing the 1099-NEC: Use your LLC's information (LLC name, EIN, and LLC address) as the payer. Even though it's a disregarded entity for income tax purposes, the LLC is still the legal entity that made the payment to your contractor. For your mixed 1099s: You're absolutely right to report both exactly as issued on your tax return. The one with your SSN goes on Schedule C as normal business income, and the one with your LLC's EIN also goes on Schedule C (same schedule). TurboTax handles this well - just make sure when you enter the LLC's 1099, you indicate it's for the same business activity. One tip that saved me headaches: Keep really good records showing which payments came through which entity. It helps during tax prep and if you ever get questions later. Don't stress too much about being late on the 1099-NEC - as long as you get it filed soon, the penalties aren't usually too severe for first-time issues. The important thing is getting it right going forward!