When it comes to 1099 reporting obligations, small and medium sized businesses need to be organized in order to ensure compliance throughout the reporting season. January can be a stressful month for small teams, but staying organized is one of the easiest ways SMBs can stay ahead of compliance and avoid tedious IRS Notices and associated penalties during reporting season.
However, 1099 reporting isn’t just something businesses can focus on in January and forget about until the next year, it is a process that takes planning and preparation throughout the calendar year. With eFileMyForms’ year-round checklist built for SMBs, teams of all sizes can ensure they’re following the correct processes and staying compliant with 1099 reporting from January to December.
January
File and deliver your forms
→ File your 1099-NEC forms with the IRS and send copies to recipients by January 31.
→ If you file W-2s, those go to the SSA on the same day.
→ eFile early to avoid IRS site delays at the end of the month.
Print & mail
→ Send forms electronically or by mail to your recipients.
→ Double-check addresses or email delivery options before sending.
Review your data
→ Verify that payee names and TINs match IRS records. A bulk TIN match is the fastest way to check your entire vendor list.
→ Fix any missing or invalid data before filing.
February
Manage corrections
→ If you spot an error on a filed 1099, file a corrected return right away.
→ Keep copies of all corrected forms sent to recipients for your records.
Catch up on other forms
→ Address any late originals for forms 1099-NEC and W-2 forms
→ First tier penalties apply for records filed within 30 days of the filing deadline.
→ Brokers and investment forms (like 1099-B) are due mid-month — if you’re a CPA, keep clients on track.
→ If needed, File Extension of Time (8809), which allows 30 extra days to file with the IRS
Plan for next year
→ Note what slowed you down this season — whether it was missing W-9s, outdated addresses,
or data from multiple systems.
March
IRS eFile deadline
→ eFile 1042-S froms with the IRS and furnish recipient statements by March 15th
→ For most 1099s filed electronically, the IRS deadline is March 31 (unless you filed for an extension).
→ Verify your TINs
→ Run a Bulk TIN check before filing to prevent “B-Notice” penalties later
Verify your TINs
→ Run a Bulk TIN Check before filing to prevent “B-Notice” penalties later.
Extensions
→ If needed, File Extension of Time (8809), which allows 30 extra days to file with the IRS
April
Review your process
→ Identify what worked well and what needs improvement for next year
→ Update templates or filing software configurations while details are fresh.
Fix lingering issues
→ File any remaining late originals or corrections.
→ Keep an eye out for any IRS notices about missing or incorrect TINs
May–June
Plan Improvements
→ Budget time or resources to simplify next year’s process
→ Consider switching to an eFile solution that automates validations, efiling, print and mail, and corrections.
Verify new vendors
→ Collect a W-9 for every new vendor or customer you onboard
→ Run a TIN check on each new payee and make this an ongoing year-round process.
July–August
Watch for penalty letters
→ 972CG “P Notices” may arrive mid-summer for missing or invalid filings.
→ Gather documentation showing you verified TINs, evaluated backup withholding requirements, and applied withholding when necessary
→ Respond within 45 days to request abatement if you have proper documentation supporting your compliance efforts.
Clean your data
→ Run another Bulk TIN Match before year-end to catch invalid records early.
Start prep early
→ Begin gathering vendor lists and payment reports so you’re ready for fall cleanup.
September–October
Handling IRS CP2100(A) Notices
→ If you recieve a CP2100 (IRS B-Notice), it means the IRS found invalid Name/TIN combinations
→ Prepare a plan for handling B-Notices, including your solicitation and response handling processes
→ Review the Name and TIN mismatches to determine whether first or second B-Notice rules apply
→ Send required solicitations on time and keep documentation of all attempts to obtain correct information.
Know your data
→ Ensure you have validated W-9s and complete taxpayer information for all payees.
→ For any missing information, solicit recipients with an updated W-9 form as soon as possible
Train your team
→ If others help with filing, make sure they know about all regulatory requirements including deadlines, forms, filing thresholds, and system logins.
November–December
Run final TIN Checks
→ Validate all vendor and payee data before the new year.
Review deadlines
→ Set internal due dates for data collection, review, and filing. Team alignment for 1099 reporting is the easiest way to avoid late filings, corrections, and penalties.
Filing Readiness Check
→ Gather test files and sample data to confirm your team understands each step of the filing process
→ Run a pilot test in your eFile system to ensure templates, filing formats, and required fields remain accurate
→ Use the test results to update instructions and align your team before January
Test your software or login
→ Confirm your filing account is active and ready for January 31.
Ready for easy, compliant 1099 filing?
Get started with eFileMyForms today
Download here: Year-Round 1099 Reporting Checklist