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
→ Make sure payee names and TINs match IRS records (you can TIN match any time of year).
→ Fix any missing or invalid data before filing.
February
Handle 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.
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→ Note what slowed you down this season — whether it was missing W-9s, outdated addresses,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
→ For most 1099s filed electronically, the IRS deadline is March 31 (unless you filed for an extension).
→ Deadline for eFiling forms 1042 & 1042-S
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
→ What worked this filing season? What didn’t?
→ Update your spreadsheet templates or filing software setup now, while details are fresh.
Fix lingering issues
→ File any late originals or corrections.
→ Stay alert for any IRS notices about missing or incorrect TINs.
May–June
Check for IRS Notices
→ Prepare a plan for potential IRS Notices: CP2100 & 972CG
→ If you receive a CP2100 (IRS B-Notice), it means the IRS found invalid Name/TIN combinations.
Fix those records now.
Verify new vendors
→ Anytime you add new contractors, collect a valid W-9 and run a quick TIN check.
Plan improvements
→ Budget time or resources to simplify next year’s process — consider switching to an
eFile solution if you’re still paper filing.
July–August
Watch for penalty letters
→ 972CG “P Notices” may arrive mid-summer for missing or invalid filings.
→ Respond within 45 days to appeal or fix issues.
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
Review IRS & state updates
→ Check for any changes in 1099 rules, filing formats, or state requirements.
Know your data
→ Ensure you have all of the correct vendor data via W-9 or otherwise to limit information return penalties for the upcoming filing season.
→ For any missing information, solicit recipients with an updated W-9 form ASAP.
Train your team
→ If others help with filing, make sure they know new deadlines, forms, or 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.
Communicate with clients or vendors
→ Send reminders for missing W-9s before everyone disappears for the holidays.
Test your software or login
→ Confirm your filing account is active and ready for January 31.
Get started with eFileMyForms today and download the Year-Round 1099 Checklist below to guide your workflow.
Download here: Year-Round 1099 Reporting Checklist