1099 Compliance Included
Januar Only: Free 1099 Filing When You Become a Bookkeeping Client
When you start monthly bookkeeping by mid-January, we’ll file your required 1099 forms for FREE—so you don’t have to worry about deadlines or penalties.
Serving growth-minded business owners since 2003
1099 Filing: what to review
before January
If you paid contractors, freelancers, or service providers this year, a quick review now can save you a stressful scramble later. Here’s the simple checklist, common mistakes, and what you need to collect.
Educational resource only (not legal or tax advice). If you have a specific situation, we recommend confirming requirements with your tax professional.
What you’re required to collect (the basics)
- Get a W-9 before paying an independent contractor. If you can’t obtain a taxpayer ID, you may be required to withhold 28% as “backup withholding.”
- Take a firm stance on W-9s. Missing info can create end-of-year penalties and headaches.
- Written agreement recommended. Consider a written agreement/work order for contractor work.
Common 1099 mistakes we see
- Paying contractors first and asking for W-9s later
- Not tracking totals across payment methods
- Assuming “my CPA will handle it” without having complete vendor info
- Missing TIN/SSN/EIN info (which can trigger penalties)
Penalty examples referenced in the guide: $50 for missing ID numbers and $50 for unsubmitted 1099s.
Who typically receives a 1099?
- Non-corporate service providers paid $600+ are typically issued a 1099.
- You generally don’t issue 1099s to corporations—but it’s still smart to have anyone claiming to be a corporation complete a W-9.
- Exception: attorneys generally require a 1099 for any amount, whether incorporated or not.
Fast FAQ
What’s the difference between an employee and a contractor?
In general, employees work under your direction (hours/conditions you control), and payroll taxes are withheld. Contractors typically control how/when they work and invoice you for services, among other factors.
What if a contractor won’t provide a W-9?
The guide notes that if you can’t obtain an identification number, you may be required to withhold 28% (“backup withholding”) and send it to the IRS.
What are the key 1099 deadlines?
Most 1099 forms must be filed and provided to contractors by January 31. Waiting until January often means rushed reviews, missing information, and unnecessary stress.
What about 1099-Ks (credit cards, PayPal, Stripe, etc.)?
Payment processors may issue 1099-Ks for credit card or platform payments, while businesses typically issue 1099-MISC for check or cash payments. This means income can be split across multiple forms.
Why handle this before January?
Because the hardest part is gathering accurate vendor info (W-9s, totals, addresses). Doing it early keeps you out of the year-end rush and reduces mistakes.
Need help getting your 1099s organized?
December-only note:
Businesses that start monthly bookkeeping with us in December can have their
required 1099 filings handled at no additional cost
as part of onboarding.
It’s simply our way of helping new clients start the year clean and organized.