
The 1099 season comes fast. If your 2025 filing felt like a scramble, now’s the time to get ahead. The IRS requires US businesses to file 1099s for certain vendor and contractor payments. If you delay or file incorrectly, you could face penalties ranging…

The 1099 season comes fast. If your 2025 filing felt like a scramble, now’s the time to get ahead.
The IRS requires US businesses to file 1099s for certain vendor and contractor payments. If you delay or file incorrectly, you could face penalties ranging from $50 to $290 per form.
CloudCFO helps US startups, CFOs, and finance teams stay compliant with 1099 compliance through tech-enabled, outsourced accounting support. The guide below will walk you through the essentials and how our team supports you from prep to filing.
A 1099 form reports payments made to people who aren’t on your payroll, like freelancers, consultants, or service providers.
You must issue a 1099 if you paid $600 or more in a calendar year for:
Tip: State-level rules may differ. If you operate in a state with income tax, additional filings may be required.
You must file a 1099 if:
| Scenario | File 1099? | Why? |
|---|---|---|
| Paid $1,200 to a freelance designer via bank transfer | Yes ✅ | Non-employee, over $600. |
| Paid $750 to a landscaping company (LLC) by check | Yes ✅ | LLC is treated as a sole proprietor |
| Paid $2,000 to an attorney (incorporated) for legal services | Yes ✅ | Lawyers must be issued 1099s even if they’re a corporation |
| Paid $800 to a cleaning service that provided a W-9 with an EIN | Yes ✅ | They’re not an employee and were paid more than $600 |
You don’t need to file if:
| Example | File 1099? | Why Not? |
|---|---|---|
| Paid an employee wages | No ❌ | Report on W-2, not 1099 |
| Paid $400 to a freelance writer | No ❌ | Below the $600 threshold |
| Paid a contractor using a credit card | No ❌ | Processor (Visa, PayPal, etc.) will issue a 1099-K, not you |
| Paid a C-corp $5,000 for software services | No ❌ | Most corporations are exempt from 1099 reporting (except legal or medical) |
| Form | Send to Vendor | File With IRS (Paper) | File With IRS (E-file) |
|---|---|---|---|
| 1099-NEC | January 31 | January 31 | January 31 |
| 1099-MISC | January 31 | February 28 | March 31 |
Late filing penalties range from $50 to $290 per form, depending on how delayed your filing is.
To stay compliant and avoid stress, collect this information early:
As part of our outsourced accounting and bookkeeping services, we take care of 1099 e-filings from start to finish:
We identify which vendors require a 1099 based on your books.
We ensure you have accurate W-9s on file and help you request missing info.
We review your accounting system, QuickBooks, Xero, AppFolio, or others, and check vendor payments to ensure your 1099s are accurate.
We prepare a summary and let you review before filing to avoid errors.
When possible, we e-file your 1099s through an IRS-approved service like QuickBooks Online, AppFolio, or another trusted provider. We also make sure your contractors get their copies, either by email or mail, depending on what the system allows or your preference.
Most businesses now e-file their 1099s, it’s faster, cheaper, and more accurate.
Need Help with 1099s? Let’s Talk.
Whether you’re scaling your finance function or want peace of mind this tax season, CloudCFO is here to help.
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Trusted by CFOs and startup founders across the US
Email us at hello@cloudcfo.ph
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Questions about how this affects your business? Our team replies within one business day.