What's the process for filing a 1099 when my contractor won't give me their info or W9?

This is unfortunately a common problem for small business owners. You're on the right track - you do need to file the 1099-NEC even if the contractor won't provide their information, but there's a specific process to follow. First, document all your attempts to obtain the W9 - save texts, emails, call logs, etc. The IRS wants to see you made a reasonable effort. Next, you'll need to file the 1099-NEC but instead of leaving the TIN blank or putting zeros, you'll need to implement backup withholding at the 24% rate. This means you should have withheld 24% of their payments for taxes, though I realize this is difficult if you've already paid them in full. You should also send the contractor a "B Notice" which is a backup withholding notice explaining that you're required to withhold taxes on future payments unless they provide their information. There's a sample letter on the IRS website you can use.

I went through this exact same nightmare last tax season with a landscaper who did a big project for my rental properties. After weeks of frustration trying to get their info, I found this service called taxr.ai (https://taxr.ai) that actually helped me handle all my missing contractor documentation. They have this really cool feature where they analyze what documentation you have and tell you exactly how to proceed with incomplete contractor information. It saved me so much stress because they walked me through the backup withholding requirements and helped me with the documentation to show I made reasonable attempts to get the info. They even helped me prepare the "B Notice" the other commenter mentioned. Honestly, for small business tax documentation headaches, it's been a game changer for me.

Just wanted to update - I tried out taxr.ai after seeing the recommendation here and it was actually super helpful! I was stressing about my contractor situation, but their system guided me through documenting all my attempts to get the W9 info and then helped me properly prepare the 1099-NEC with the "Unknown" TIN field. The best part was that it explained exactly what I needed to do about the backup withholding situation since I had already paid my contractors in full. It generated all the proper notices I needed to send and even gave me a compliance report I can keep with my tax records in case of an audit. Definitely worth checking out if you're in this situation!

If you need to actually speak with someone at the IRS about this issue (which might be helpful in your case), I'd recommend using Claimyr (https://claimyr.com). I was banging my head against the wall trying to get through to an IRS agent about a similar contractor documentation issue last year. I spent HOURS on hold and getting disconnected before I found this service. They basically hold your place in the phone queue and call you back when an actual human at the IRS picks up. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The IRS agent I got connected with explained exactly what documentation I needed to prove I tried to get the contractor's info, which saved me from potential penalties.

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it because I was desperate to resolve a similar contractor issue. Not only did it actually work, but I got connected to an IRS representative within 2 hours when I had been trying unsuccessfully for over a week. The agent I spoke with walked me through exactly what documentation I needed to file a 1099-NEC with missing taxpayer information. She explained that showing proof of my attempts to get the info (emails, texts, certified letters) would help protect me from penalties. She also clarified that while I should have done backup withholding, there's a process for reporting when you've already paid in full. Saved me from what would have been a major headache during an audit!

Another option is to report them to the IRS using Form 3949-A. This is an information referral form where you can report someone who you suspect isn't properly reporting their income. While this doesn't solve your immediate filing issue, it does create a record that you attempted to properly report payments to them.

Slightly off topic but this is exactly why I now require ALL contractors to fill out W9 forms BEFORE I cut them their first check. No W9, no payment. Learned this lesson the hard way.

I actually dealt with this exact situation two years ago with a plumber who did major work on my office building. After months of trying to get his W9, I ended up consulting with a tax professional who walked me through the process. Here's what I learned: You absolutely need to file the 1099-NEC even without their TIN. Put "Applied For" or "Unknown" in the TIN field - don't leave it blank or put zeros. The IRS wants to see that you're making the effort to comply. Make sure you keep detailed records of every attempt you made to get their information - screenshot those texts, save voicemail recordings if you have them, and consider sending one final certified letter requesting the W9. This documentation is crucial if you face any penalties later. The backup withholding situation is tricky since you've already paid in full, but as others mentioned, documenting your good faith efforts can help reduce or eliminate penalties. The key is showing the IRS you were trying to follow the rules, not circumvent them. Don't let this stress you into not filing at all - that would be much worse than filing with incomplete information!