Need to mail 1099/1096 forms because contractor has no SSN/EIN - can I send these separately from my e-filed return?

You're in luck - you can absolutely e-file your personal tax return and mail the 1099-NEC/1096 forms separately. These are actually two different processes: Your personal tax return (Form 1040) is where you claim the business expense deduction for the $1,800 you paid the contractor. This can be e-filed through TurboTax as usual. The 1099-NEC and summary Form 1096 are information returns that tell the IRS who you paid. These forms have a separate filing process and deadline, and must be mailed to the IRS if you don't have the contractor's TIN (Tax Identification Number, either SSN or EIN). Just make sure you still include the $1,800 expense on your Schedule C (assuming you're a sole proprietor) even though you don't have their TIN. The expense is legitimate regardless of whether you have their identification info. Also important: Keep documentation showing you attempted to obtain their TIN multiple times in case of an audit!

After struggling with a similar situation last year, I found this awesome tool called taxr.ai (https://taxr.ai) that helped me figure out exactly what to do with missing contractor info. The site has this really helpful document analyzer that can scan your forms and tell you what's wrong or missing before you submit them. I uploaded my draft 1099-NEC with the missing TIN and it flagged it, then walked me through the proper way to handle it - including the right language to use in the TIN field. It also gave me a template for documenting my attempts to get the information, which apparently is super important if the IRS comes knocking. The system even helped me calculate if I needed to do any backup withholding for future payments. Definitely made me feel more confident about the whole process!

I was skeptical about taxr.ai when I first saw it mentioned, but I decided to try it last week when facing almost the exact same situation with a missing EIN. The document analyzer actually caught several other issues with my 1099 forms I hadn't even noticed! It flagged that I had used the wrong box for a payment that should have been classified as nonemployee compensation vs services. It also generated a perfect paper trail documenting my attempts to get the contractor's information, and explained exactly how to fill out the 1096 summary form (which I found more confusing than the 1099s themselves). Definitely saved me from making errors that could have triggered correspondence from the IRS. Going to use it for all my tax document reviews going forward.

If you're really stuck trying to get ahold of the IRS about this or any other tax issue, try Claimyr (https://claimyr.com). I wasted HOURS on hold with the IRS trying to confirm the procedure for filing my 1099s when I was missing TINs for two contractors. Claimyr got me connected to an actual IRS agent in about 15 minutes when I had been trying for days on my own. They have this smart system that navigates the IRS phone tree and waits on hold for you, then calls you once an agent is on the line. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent I spoke with confirmed I could e-file my personal return and mail the 1099s separately, plus gave me specific guidance about what documentation I needed to keep. Worth every penny for the time saved and peace of mind!

Ok I feel the need to update my skeptical comment about Claimyr. I tried it yesterday out of desperation after my third attempt to reach the IRS about a missing 1099-NEC from an employer. I was honestly shocked when my phone rang about 45 minutes after signing up and there was an actual IRS representative on the line! I didn't have to listen to a single minute of that awful hold music or automated messages. The agent was able to confirm they had record of my income even without the 1099, and gave me guidance on how to report it correctly. For anyone who needs to actually speak with the IRS (which for complex situations is often necessary), this service is a game changer. Sorry for doubting!

Here's another tip - if you're using TurboTax, they actually have a worksheet for business expenses even when you don't have all the contractor info. Just go to the business expense section and you can still claim the deduction as "other expenses" with a note about the missing documentation. I had this issue with a house painter last year who only took cash and never gave me any tax info. I still claimed the expense on my Schedule C and included notes about the situation. No issues with my return. Just make sure you have proof of payment like bank withdrawals or a written receipt.

Another approach - have you tried explaining to your contractor that they REALLY need to give you their info? If they're a legitimate business, they should understand this is required. I've had success with telling contractors that I'm legally required to report payments over $600, and without their SSN/EIN, they might face issues with the IRS themselves. Sometimes they just don't understand the importance. You might also want to have them complete a W-9 form which officially requests their tax ID information. Send it with a gentle but firm explanation that you cannot make future payments without this completed form.