W2 Issues/Concerns

  • This field is for validation purposes and should be left unchanged.


Check out our weekly blog posts and see the latest news and discussions happening in the HR world of business.

Top HR Checklist for 2019

If you’ve made the promise that 2019 is the year that you’re FINALLY going to get organized, this is the checklist for you. It includes dates that you as a business owner should have on your calendar in order to stay on top of various HR-related tasks and deadlines even when you work with a Professional Employer Organization (PEO).

This year is particularly important because the Affordable Care Act has ushered in a brand-new set of very important deadlines, such as for filing forms 1095-C, to ensure compliance with Obamacare updates.


  • Tuesday, January 1:
    • New Year’s Day (federal holiday)
    • Coverage begins for 2019 health insurance plans for individuals who purchased coverage through the Marketplace
  • Monday, January 21: Martin Luther King Day (considered a federal holiday)
  • Monday, January 28: The official kick off of the 2019 tax season (which the IRS has confirmed will go ahead, even if the government shut-down continues past this date)
  • Tuesday, January 31:
    • Deadline to file form 941 (reporting on the fourth quarter of 2018).
    • Deadline for employers to hand out W-2’s to employees and 1099s to others who performed work in 2018.
    • Deadline for employers to file W-2s, W-3s, and Forms 8027, 1099 and 1096 with the appropriate agencies.
    • Deadline for employers to give employees Form 1095-C. However, it should be noted that for 2019 only, the IRS has issued an extension for employers, extending the deadline to March 4, 2019.
    • Deadline to deposit the Federal Unemployment Tax Rate (FUTA) where applicable.
    • Deadline to file Form 945 to report any non-payroll federal income tax withholdings (if you deposited all taxes on schedule, your filing date moves to February 10).


  • Friday, February 1: Kick off for Forms 300 and 300A (related to OSHA) to be posted in all non-exempt workplaces (you have until April 1 to complete this).
  • Friday, February 15: Final day to pay employee bonuses that qualify toward 2018 business taxes.
  • Monday, February 18: President’s Day (federal holiday)
  • Thursday, February 28:
    • Deadline to physically file paper versions of Forms 1094-C and 1095-C, as well as paper versions of Forms 1099 and 1096.
    • Deadline to request a new Form W-4 from exempt employees (those who claimed to be exempt from income tax withholding in 2018).


  • Friday, March 1: National Employee Appreciation Day (not a federal holiday, but it might be nice to recognize your employee’s hard work with a treat at some point during the day, or even just an email to share your thanks if money is tight!).
  • Friday, March 1: Forms W-4 claiming exemption from withholding for the previous year expire.
  • Friday, March 15: Deadline to file S Corp and partnership tax returns.
  • Sunday, March 31:
    • End of Q1 (calendar year).
    • Deadline to submit EEO-1 survey data selected from a payroll period from Q4 of the calendar year 2018.


  • Monday, April 1:
    • Deadline to electronically file (e-file) Forms 1094-C and 1095-C.
    • Deadline to e-file Forms 1099, 1096, and 8027.
      “April Fool’s Day” so be careful of any too-good-to-be-true business propositions or pranks!
  • Monday, April 15: Deadline to submit individual tax returns.
  • Wednesday, April 24: Administrative professional’s day (if you have admin staff that help you to hold down the fort, now is time to show them your appreciation!)
  • Tuesday, April 30: Deadline to file your quarterly tax return (Form 941).


  • Monday, May 27: Memorial Day (federal holiday).


  • Sunday, June 30: End of Q2 (calendar year).


  • Monday, July 1: Deadline for companies in certain high-risk industries, or those with 250+ employees in industries covered by OSHA’s recordkeeping regulation to submit Forms 300A, 300, and 301 for 2018.
  • Thursday, July 4: Independence Day (federal holiday).
  • Wednesday, July 31: Deadline for employers to file their quarterly tax return (Form 941).

September (because really, there’s nothing due in August!)

  • Monday, September 2:
    • Labor Day (federal holiday)
    • Start of National Payroll Week (so if you have folks that run payroll, now’s the time to send some thanks their way!).
  • Monday September 30: End of Q3 (calendar year).


  • Monday, October 14: Columbus Day (federal holiday)
  • Tuesday, October 15: Individual tax return deadline for individuals who filed for an extension.
  • Thursday, October 31: Deadline to file your quarterly tax return (Form 941).


  • Friday, November 1: Enrollment kicks off for individuals seeking health insurance coverage through the federal Marketplace.
  • Monday, November 11: Veterans Day (federal holiday)
  • Thursday, November 28: Thanksgiving Day (federal holiday)
  • Friday, November 29: Remind employees to submit a new Form W-4 if their withholding allowances have changed or are expected to change in 2020.


  • Sunday, December 15: Open enrollment period ends for 2020 health insurance plans for individuals through the Marketplace.
  • Wednesday, December 25: Christmas Day
  • Tuesday, December 31: End of Q4 (calendar year)

Compliance issues, an area of HR that is constantly evolving and shifting, making it very hard to keep up with and a full-time job in itself. From keeping track of and understanding Obamacare updates to updating the employee handbook, an off-site HR pro can handle these administrative tasks to free you up to focus on higher-value tasks such as long-term strategic planning.

Featured BLOGS

  • Why Is It Important To Have Yearly Reviews With Your Employees?

    If you’ve hung around here for a while, you know that we’re big fans of giving feedback regularly to employees. We love the idea of informal check-ins, coaching in the moment, high fives for a job well done, and even just more frequent performance reviews. With all this informal feedback flying around, it’s easy to see how the annual review could get lost in the shuffle. However, there is certainly a business case for why it remains an important component in the small business world. Below, we outline the most important benefits of the formal review. It creates a lasting

  • What Is Co-Employment?

    If there’s one thing small business owners don’t need in their life, it’s another buzz word. But, alas, 2020 has rolled around and suddenly folks are talking about the concept of co-employment. Below, we outline what it is, how it can benefit your business, and what you’ll want to consider before you enter into this type of relationship. What is it?The National Association of Professional Employer Organizations (NAPEO) defines co-employment as the “contractual allocation and sharing of certain employer responsibilities between the PEO and the client.” If that doesn’t clear it up – and it didn’t for us either! –