Every January, finance and operations managers face the same scene: stacks of forms, a printer running nonstop, and staff members stretched thin as they try to meet IRS deadlines. One late form or one wrong taxpayer ID can throw the whole process off. The scramble is frustrating and risky.
The numbers show why it matters. According to the IRS’s latest projections, businesses will file 456.9 million information returns in calendar year 2025. That’s a 7.7% jump over the previous year. That volume is only growing.
Additionally, the IRS now requires e-filing for individuals submitting 10 or more returns. Add in the January 31 deadline for 1099-NEC, and it’s no surprise many teams burn the candle at both ends just to stay compliant.
There are smarter ways to navigate the chaos. Let’s examine three practical steps you can take before year-end to simplify 1099 processing and avoid the annual scramble.
1) Automate Your 1099 Workflow
Think about how much time your team spends chasing down W-9s, double-checking names against tax IDs, or calculating who passes the $600 threshold. When tasks are performed manually, errors are almost guaranteed.
The IRS commonly flags mistakes like misspelled names, math errors, or incorrect Social Security Numbers. Every error costs time, and sometimes money, when corrections must be filed.
Automation flips the script. Instead of spreadsheets and sticky notes, you’ve got a system that works for you:
- It performs TIN matching in real-time, reducing errors.
- It flags payments that cross the $600 threshold so you’re not second-guessing.
- It tracks vendors who are missing W-9s.
- And when you’re ready, it pulls everything together into digital files you can send straight to the IRS.
Imagine checking a dashboard in October that already tells you which vendors are missing information. The payoff is less risk of IRS notices, fewer corrections, and a cleaner audit trail. And let’s not forget the hours saved. Automation makes 1099 services proactive instead of reactive.
2) Outsource 1099 Forms to Break the Bottleneck
Even with automation, someone still needs to deal with the physical aspects of printing, stuffing, and mailing. For small teams, it’s exhausting. For larger ones, it can be a logistical nightmare. That’s where outsourcing comes in.
When you outsource 1099 forms, you’re cutting out busywork that doesn’t need to live on your team’s desk. A strong provider can:
- Handle bulk 1099 printing and mailing, with tracking included.
- Manage returned mail securely.
- Correct errors and re-file quickly.
- Ensure compliance with both federal and state regulations and requirements.
Outsourcing often feels like getting a piece of January back. Instead of burning overtime hours printing and mailing stacks of forms, finance teams can hand that work to a specialist. With the heavy lifting out of the way, staff stay focused on closing the books, preparing reports, and handling the strategic work that really matters.
Outsourcing also adds an extra layer of compliance protection. Vendors that live and breathe tax forms know how to avoid pitfalls that in-house staff may not. Yes, you need to vet for security and reputation, but the benefits are hard to ignore.
If your people spent last January buried under paper, outsourcing could be the smartest decision you make this Q4.
3) Go Paper-Light With Digital Delivery and E-File
Paper is expensive, slow, and unreliable. Addresses change, envelopes get lost, and postage costs continue to rise. Moving toward digital filing and delivery cuts through all of that.
Here’s what changes when you make the shift:
- E-filing extends the deadlines for certain forms, such as the 1099-MISC, from February 28 to March 31. That extra time can be a lifesaver.
- Contractors and vendors get faster access to their forms through secure online delivery.
- Every step is traceable. You’ll know whether a form was delivered, opened, or bounced back.
The cost savings are real, too. Fewer envelopes, less postage, and less staff time spent babysitting printers. For businesses filing hundreds of forms, that’s money back in your budget.
You don’t need to go all digital in one leap. Many companies start with an opt-in option for vendors who prefer electronic delivery. The important step is setting up a system that handles both e-file and paper distribution seamlessly.
When you shift to digital-first 1099 services, you’re building resilience into your process.
Q4 Prep: A Practical 1099 Readiness Checklist
Want January to feel less like a sprint? Here are ten things you can do right now:
- Mark your IRS deadlines (January 31, February 28, March 31).
- Determine who will be responsible for 1099 oversight this year.
- Collect any missing W-9s from vendors.
- Run early TIN matching to catch ID issues.
- Flag all vendors hitting the $600 threshold.
- Choose e-file, paper, or a hybrid strategy.
- Verify addresses for vendors who still want paper.
- Do a test e-file run before year-end.
- Line up an outsourcing partner for bulk 1099 printing and mailing.
- Block time for a short post-filing review in February.
Every step you take in Q4 removes one headache in January. Even small moves now pay big dividends later.
The Bottom Line: Let CheckIssuing Take the Stress Out of 1099 Season
The 1099 season doesn’t have to feel like chaos. When you automate, outsource 1099 forms, and lean into digital delivery, you turn the January scramble into a smooth, predictable process.
January is rough, and you shouldn’t have to carry it alone. That’s why we at CheckIssuing set out to build our platform to relieve your team of the pressure. We step in where headaches typically accumulate, such as when firms must conduct TIN matching, clean vendor data, or address error corrections after filing. In short, we tackle the workload of 1099 processing so you can concentrate on running your business.
Some clients still need paper, and that’s fine. We manage bulk 1099 printing and mailing, complete with USPS tracking and returns. Others are ready to go digital, and we handle that, too, from e-delivery to e-file submissions with confirmation receipts.
We’ve seen finance and operations managers turn their Januarys around this way. Instead of long nights and overtime, they close their books calmly and on schedule, confident that every form is filed correctly.
If you want that same relief, don’t wait until the scramble begins. Reach out to us and we’ll work with you on a filing approach that keeps you compliant, organized, and free from the usual chaos.
Key Takeaways
- IRS 1099 requirements are increasing, with e-filing becoming mandatory for 10 or more forms in 2025.
- Automating 1099 workflows reduces errors, flags missing W-9s, and saves staff time.
- Outsourcing 1099 printing and mailing removes bottlenecks and adds compliance expertise.
- Shifting to e-file and digital delivery cuts costs, improves tracking, and extends deadlines.
- Preparing in Q4 with checklists, early TIN matching, and outsourcing partners makes January less stressful.
Footnotes / Citations
- Internal Revenue Service (IRS) – Projections for Business and Individual Tax Returns, 2025
- IRS – Electronic Filing Requirements for Information Returns
- Association for Financial Professionals (AFP) – 2025 Payments Fraud and Control Report (citing 1099-related fraud context)
Last updated: September 2025