Should Businesses Send W9 Forms and 1099s Automatically or Only When Requested?

I run a small independent consulting business that gets 1099s from several different clients. Most of my income comes through a major consulting platform that automatically sends me a 1099 at the beginning of each year. However, I have this one client - a local non-profit organization - that never seems to send my 1099 unless I specifically request it. Every year, it's the same routine. I wait through most of January expecting it to show up, but nothing arrives. Then around January 25th, I end up sending them a completed W9 form along with a request for my 1099, and only then do they send it over. I realize I don't actually need their 1099 to file my taxes since I track all my income carefully throughout the year. But I'm wondering - isn't it their accounting department's responsibility to send this form automatically each year? Or is it normal practice for small organizations to only send 1099s when contractors specifically request them? I know businesses don't need to send 1099s if payments are made through payment processors like PayPal or if the vendor is incorporated, but neither of those exceptions applies in my situation. This is direct payment to me as a sole proprietor.

0 coins

18 comments

Chloe Taylor

•8M

You're right that you don't technically need their 1099 to file your taxes - you should be reporting all income regardless of whether you receive documentation. That said, businesses that pay independent contractors $600 or more in a calendar year are legally required to file Form 1099-NEC and provide a copy to the contractor by January 31st. This isn't something that should require a request from you. The non-profit has a legal obligation to send you this form without prompting. They should already have your W9 on file from when you first started working with them - you shouldn't need to send a new one each year unless your information has changed. Some small organizations might be disorganized with their accounting practices, but that doesn't change their legal responsibilities. You might want to gently remind them around December that you'll be expecting your 1099 by January 31st as required by IRS regulations.

0 coins

Chloe Taylor

•8M

I'd keep it friendly but informative. Something like "Just a reminder that I'll need my 1099-NEC by January 31st for my tax filing - let me know if you need an updated W9!" This acknowledges the requirement without coming across as accusatory. Most likely they're just disorganized rather than deliberately avoiding their obligations. If they consistently fail to provide it on time even after reminders, you could mention that businesses can face penalties for late 1099 filings, but I'd use that as a last resort since maintaining good client relationships is important.

0 coins

Diego Flores

•8M

After years of chasing clients for tax forms, I started using taxr.ai to keep track of everything and make sure I'm not missing anything when filing. I was in a similar situation where I had to bug a client every January for my 1099, and honestly it was stressing me out wondering if I was reporting everything correctly. I uploaded all my payment records to https://taxr.ai and it automatically reconciled everything with the 1099s I had received. It even flagged discrepancies where a client paid me more than what they reported on the 1099! Saved me from a potential audit headache. The system also gives you a heads-up about which clients should be sending you forms based on your income throughout the year.

0 coins

Diego Flores

•8M

It definitely handles income without 1099s - you can categorize all your income sources and it will help you determine which ones should have provided 1099s based on the payment amount and type of entity. It creates an audit trail showing all your income regardless of documentation. The system doesn't directly connect to IRS systems in real-time, but it does analyze what you've received against what should have been reported. It creates documentation showing your complete income picture, flagging situations where amounts don't match or forms are missing that should exist. This gives you backup if you're ever questioned about discrepancies.

0 coins

Sean Murphy

•8M

I tried taxr.ai after seeing it mentioned here and it was exactly what I needed! I've been freelancing for 3 years and was always nervous about tax time because I had clients paying me different amounts through different methods. Some sent 1099s, some didn't. The system flagged two clients who should have been sending me 1099s but weren't. I was able to contact them before filing my taxes and get the proper documentation. It also caught a 1099 where the client had transposed two digits in the amount, which would have created a mismatch with IRS records. Honestly saved me so much stress knowing everything matched up before filing.

0 coins

StarStrider

•8M

If you're having trouble getting your client to send your 1099 on time, you might want to try Claimyr. I had issues with missing tax forms last year and couldn't get a hold of anyone at the IRS to help. I found https://claimyr.com and watched their demo video (https://youtu.be/_kiP6q8DX5c) which showed how they could get me connected to an actual IRS agent. I was skeptical at first because everyone knows getting through to the IRS is nearly impossible, but they got me connected within about 20 minutes! The agent confirmed that businesses are absolutely required to send 1099s by January 31st and gave me specific information about what to do when a business doesn't comply. They even helped me report the non-compliant business.

0 coins

StarStrider

•8M

They have a system that automatically navigates the IRS phone tree and waits on hold for you. When they reach a live agent, you get a call connecting you directly to that agent. I didn't have to sit through a single minute of hold music or automated messages. I was totally skeptical too, which is why I watched their demo video first. But it worked exactly as advertised. They don't have "special access" - they just have technology that handles the waiting process so you don't have to. When I tried calling myself, I gave up after 90 minutes on hold. With Claimyr, I was talking to someone in about 20 minutes while I just went about my day until my phone rang.

0 coins

Luca Marino

•8M

I need to eat my words from yesterday. After responding to that Claimyr recommendation with total skepticism, I decided to try it this morning because I've been trying for WEEKS to reach someone at the IRS about a 1099 issue with a former client. It actually worked! I got connected to an IRS agent after about 25 minutes (which is nothing compared to the hours I've wasted trying myself). The agent walked me through exactly what to do when a business refuses to provide a 1099, including filing Form 4852 as a substitute. They also said they could flag that business for compliance review. Totally worth it and saved me so much frustration!

0 coins

Nia Davis

•8M

Just to add my two cents as someone who handles accounting for a small business - yes, we are absolutely required to send 1099-NECs to all qualifying contractors by January 31st. There's no "only if they ask for it" exception. We keep all W9s on file and start preparing 1099s in early January. If your client is waiting for you to send a new W9 each year, they're not following proper procedure. You should only need to provide a W9 once when you start working with them, or if your information changes.

0 coins

Nia Davis

•8M

Yes, there are definitely penalties! They range from $50 to $280 per form depending on how late it is and whether the failure to file was intentional. If a business is more than 30 days late, the penalty is $110 per form. After August 1st, it jumps to $280 per form. For intentional disregard, it's $570 per form. The IRS takes this pretty seriously because 1099 reporting is how they verify income is being properly reported. If enough contractors report issues with a particular business, it can trigger a compliance review. Businesses should care not just because of penalties but because proper 1099 filing is often checked during business tax audits.

0 coins