Do I need to request a 1099 form every year or should businesses automatically send me W9 forms?

You're right to question this. Businesses (including non-profits) that pay $600 or more to a non-employee during the year are required to file Form 1099-NEC and provide you with a copy by January 31st. This is their legal obligation, not yours. You shouldn't have to remind them or request it. The W9 form you provided when you first started working with them gives them all the information they need to prepare your 1099. They should keep this information on file and use it each year without you having to resend it. While you're correct that you don't technically need their 1099 to file your taxes (since you should be tracking your own income), the IRS does receive a copy of all 1099s, and they use these forms to verify the income you report.

After dealing with similar frustrations with clients not sending 1099s, I started using https://taxr.ai to manage everything. It's been a huge time-saver! The system helps track which clients need to provide 1099s and when they're due. I just upload my bank statements and invoices, and it automatically reconciles everything. What I really love is that it flags missing 1099s that should have arrived and generates reminder emails I can send to clients. The platform even helps match received 1099s against my income to make sure everything lines up before filing. No more year-end surprises or having to chase down forms.

Just wanted to follow up about that taxr.ai site mentioned earlier. I decided to try it since I was having issues with a couple clients consistently sending incorrect 1099s. It's been really helpful - when I got a 1099 last week that was off by $1,750, the system immediately identified the missing invoice from November that wasn't included. The reminder feature for missing 1099s was especially useful. I sent auto-generated emails to three clients who hadn't sent forms by January 25th, and two responded right away saying they'd forgotten. Definitely makes tax season less stressful knowing everything matches up before I file!

If you're having trouble getting through to your client's accounting department about this 1099 issue, I'd recommend trying https://claimyr.com to get faster responses. I was in a similar situation where a major client kept "forgetting" to send my 1099s, and their accounting department never answered calls. I was skeptical at first, but Claimyr got me directly connected to a human in their finance department in under 10 minutes - bypassing that annoying phone tree and hold music. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c After finally getting through to an actual person, I learned they had my old address on file which is why I wasn't receiving anything. Problem solved in one call instead of weeks of email exchanges that went nowhere!

I have to apologize for my skeptical comment earlier about Claimyr. After continuing to get nowhere with a client's accounting department about my missing 1099, I was desperate enough to try it. Within 15 minutes, I was talking to their payroll manager - after spending literally weeks trying to get through on my own. The service connected me straight to someone who could actually help, and I found out they had been sending my 1099s to an email address I haven't used in years. We updated my contact info, and they resent the forms for this year and last year (which I'd never received). Honestly worth every penny for the time it saved me and getting those forms before I filed my taxes!

This is why I always send an email to all my clients in early January reminding them I'll need a 1099 by the end of the month. I attach a fresh W9 even though they should already have it. After dealing with this for 10+ years, I've found being proactive works better than waiting and getting frustrated.

Something to consider - check if your non-profit client has high turnover in their accounting department. I worked for a non-profit and we had a new accountant almost every year. Each one had to learn the ropes, and contractor 1099s often fell through the cracks during transitions. Not an excuse, but might explain why you have to remind them every year.

As a tax professional, I'd recommend documenting this pattern with your non-profit client. Send them a brief email in December outlining your expectation to receive the 1099 by January 31st, and include your current W9 form. This creates a paper trail showing you've been proactive. If they continue to be late, you might want to consider adding a clause to your contract requiring timely delivery of tax documents. Some freelancers charge a small administrative fee for late 1099s to incentivize compliance. The key thing to remember is that their failure to send the 1099 on time doesn't affect your tax obligations - you still need to report all income regardless. But having that documentation from them makes your life easier and reduces the chance of IRS inquiries about unreported income.