Print and Mail W2s and 1099s On Time: a 6 Step Checklist for Employers

Sep 10, 2021

Year-end accounting is hard enough. Printing and mailing W2s & 1099s in January can cause a lot of stress. Use this checklist to make sure you don't miss any of the critical details!

Supplies: What employee tax forms will you need, and how many? (Order extra!) 

  • Counts – how many W2s & 1099s will you need to print, stuff & deliver? 
    • Order your forms. 
    • Order your envelopes. 
    • Make sure you have extras of everything in case of mistakes!
  • Order toner for printers. 
  • Postage – do you have a machine? Is it loaded with funds? 
Tip: Order W2s & 1099s (with matching envelopes) before January so you're ready to print & mail as soon as you wrap up year-end accounting tasks. Click To Tweet

If you print more than 500 W2s, you should consider outsourcing the process. Save yourself staffing issues, security concerns, and a huge amount of time - we have decades of experience handling W2s, 1099s + 1095s for companies like yours.

If you decide to print in-house, we have what you need to print and mail your W2s and 1099s on time. We carry a full range of IRS-approved forms compatible with all types of accounting software, with matching envelopes for every form - in stock in our warehouse for fast delivery!

Security: Protect your company from liability nightmares 

  • Keep control of your employee tax forms and the confidential information they contain 
    • Set up a secure area to print, fold, insert, and seal.
    • Does the area have doors that lock? 
    • Are employees bonded? Background checked? Drug tested? 
    • Are servers and networks secure? 

Staffing: Will you need extra time? 

  • Allocate extra payroll funds for overtime and/or additional employees. 
  • Supervisor time to monitor checks/balances/misprints/mis-stuffs. 
  • Shift priorities & workload to accommodate short turn times. 
  • Prepare for decreased productivity due to tired/overworked staff. 

Submit: Will you hit the deadlines? 

  • If you're mailing forms, double-check your data to avoid bad address returns.
  • Print, fold, stuff, and deliver your forms by the January 31 deadline.
  • Complete your federal/state filings. 
    • Get or export copies of W2s, 1099s, 1095s. 
    • Fill out your W3. 
    • Mail in the form or submit electronically by January 31. 


  • Field all of those reprint calls – or even <sigh> walk-ins - about-how-Jerry-from-Smithville-never-got-his-W2-because-he’s-changed-addresses-twice-and-employers-three-times-and-he-really-really-needs-his-W2-reprinted-so-can-you-handle-that-right-now? 
Employer tax season tip: Stock the office with Emergen-C and hand sanitizer. Stress is bad for the immune system! Click To Tweet

Sanity: Keep yourself and your staff from going off the deep end 

  • Make sure you take some vacation time in October/November. Or take the month of February off to recover.
  • Budget for snacks, drinks, lunches to boost office morale. Order pizza. A lot. 
  • Stock the office with Emergen-C and hand sanitizer - stress is bad for the immune system. 
  • Say goodbye to the month of January, because you’ll probably be too frazzled to do anything but zone out on the couch after work. Make sure your Netflix subscription is current and there’s someone who’s willing to feed you.  
  • Stock up on chamomile tea for those sleepless nights when deadlines are coming up fast. 

Tax season is never fun, but we're here to help make it as easy as possible. Let us help you find exactly what you need and take one year-end worry off your shoulders.

Order IRS-approved W2s, 1099s, and all the other tax forms, envelopes and supplies you'll need, learn more about outsourcing, or contact us for help determining the best solution for you.

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