Year end is easier when you handle it in November and December rather than January. Your payroll dashboard has a checklist with everything you need to do, and this article walks through each item. Finish it on time and your staff's W-2s will be right the first time.

Find Your Year-End Checklist

Your checklist lives at the top of your payroll dashboard and tracks what you have finished as you go. It is essential that company tax information is correctly entered. If the tax information is incorrect or missing, your tax filings will be impacted.

From your admin dashboard, navigate to the Payroll tab.
Complete your 2026 year end checklist is the first card on the page. It shows how many items you have finished.
Click into any item to work on it, or click Mark completed once you have handled it.

What's on the Checklist

Checklist item	What it covers	Due
Review tax details and preview filings	Confirm your company tax information and look at your year-end returns before they are filed	December 31
Confirm employee and contractor details	Social Security numbers, legal names, and home addresses for everyone you paid in 2026	December 31
Report any payroll paid outside of Playground	Wages, bonuses, or benefits that never went through a Playground payroll	December 14
Review your W-2 previews	Check draft W-2s against your own records before anything is filed	December 31

🚨 Item 3 is due December 14, two weeks before the rest. Anything you can fix yourself in Playground you have until December 31 to fix. Anything we have to process on your behalf needs to reach us by December 14, so there is time to complete it before the year closes.

💡 Fixing something now is quick. Fixing it after January is not. Once W-2s are filed in mid-January, a change becomes a corrected W-2 (a W-2C), which means a new form for your employee, a slower tax refund for them, and an amended filing fee for you.

Review Tax Details & Preview Filings

Checklist item 1. Due December 31.

If your company tax information is wrong or missing, your filings will be rejected or filed incorrectly. This is the fastest item on the list and worth doing first.

From your admin dashboard, navigate to the Payroll tab and click Review tax details on the first checklist item.
Confirm your federal tax information. Your EIN must match exactly what the IRS has on file.
Confirm your state and local tax account numbers. If you applied for an account number earlier in the year and have since received it, enter it now. a. If an account number is still pending, leave it marked as applied for and send it to us as soon as it arrives.
Enter your new Unemployment Insurance rate if you have received one. Use an effective date of 01/01/2027.
When everything looks right, return to the checklist and click Mark completed.

💡 Most states mail a new unemployment rate notice in December or January. Watch for it. If yours arrives after you have completed this item, enter the new rate as soon as you get it and we will reconcile any difference at the end of the quarter.

🚨 To change your company's legal name or address, email [email protected]. These cannot be edited directly because they have to match your registration with the IRS and your state.

Confirm Employee & Contractor Details

Checklist item 2. Due December 31.

A wrong Social Security number is the most common reason a W-2 is rejected by the IRS. A wrong address is why a W-2 comes back to you in February. Both are quick to fix now.

From your admin dashboard, navigate to the Payroll tab and open checklist item 2.
Review every person on the list, including staff who left during the year. They still get a W-2.
For each person, confirm: a. Legal name, exactly as it appears on their Social Security card b. Social Security number or, for contractors, their SSN or tax ID number c. Home address, which is where a paper W-2 or 1099 will be mailed d. Classification for contractors: individual or business
Click Mark completed when the list is clean.

Ask Your Staff to Check Their Own Details

Some things only your staff can confirm. They know if they moved in August or if their legal name is spelled differently than you have it.

We email your staff directly on November 5 asking them to do this, with a reminder on December 1. You do not need to forward anything. It is still worth mentioning at a staff meeting, because the ones who act on it are usually the ones who heard about it twice.

If you want to send your own message, ask staff to:

Log in at app.tryplayground.com on a computer
Open the Payroll tab and click Update Information
Go to Personal Info and confirm their legal name, date of birth, Social Security number, and home address
Check the box to receive paperless W-2 statements while they are there

📱 If you're on the Mobile App, tax documents and personal payroll information are not available. Staff need to use a web browser for this.

💡 Paperless delivery gets their W-2 to them faster. Staff who opt in can download their W-2 as soon as it is ready in January instead of waiting on the mail, and it cannot be lost or sent to an old address. For full instructions, see W-2s and 1099s for Staff.

Report Payroll Paid Outside of Playground

Checklist item 3. Due December 14, the earliest deadline on your checklist.

A W-2 has to show everything a person earned from you in 2026, not just what ran through Playground. If you paid someone outside the system at any point this year, tell us before December 14 and we will add it. We handle these for you, which is why this item is due two weeks before the others.

What Counts

Wages paid by personal check or cash, including a one-off payment to cover a missed payroll
Bonuses paid outside of a regular or off-cycle payroll
Third party sick pay from an insurance carrier
Group term life insurance over $50,000 in coverage
2% shareholder benefits
Anyone you paid in 2026 who is not in your staff list at all, including people who left before you started with Playground

How to Report It

From your admin dashboard, navigate to the Payroll tab and open checklist item 3.
Review pay history to confirm if payroll is missing.
If payrolls are missing, send an email to [email protected] with the full details of the missed payroll.
A payroll specialist will reach out to you to confirm if additional details are required.

🚨 Do not skip this because you think it is too late or too small. Unreported wages mean an incomplete W-2 for your employee and incomplete tax filings for your center. Reported by December 14, this is a routine fix. Found in February, it means amended returns for every affected quarter, and amendment fees apply.

💡 The pay date decides the tax year, not the work date. A payment dated December 31, 2026 goes on the 2026 W-2. A payment dated January 2, 2027 goes on the 2027 W-2, even if the work happened in December.

Review Your W-2 Previews

Checklist item 4. Due December 31.

You can see a draft of every employee's W-2 before anything is filed. This is your last chance to catch a problem while it is still cheap to fix.

From your admin dashboard, navigate to the Payroll tab and open checklist item 4.
Download the previews. You get a PDF for each employee and a spreadsheet with every W-2 box in one place.
Compare the totals against your own payroll records. The sum of all W-2s should match your payroll summary for the year.
Look for anyone missing from the list. If someone you paid in 2026 is not there, that is checklist item 3.
Click Mark completed when the numbers look right.

💡 Use the spreadsheet if you have more than a handful of staff. Scanning one row per employee is much faster than opening twenty PDFs, and it makes a wrong total easy to spot.

🚨 Previews refresh once a week. If you pull a payroll summary to compare against, pull it for the same date the preview was generated. Comparing a fresh summary to a week-old preview will show differences that are not real.

💡 W-2 amounts are not the same as gross wages. Pre-tax deductions like health insurance and 401(k) contributions reduce taxable wages, so the W-2 will show less than what an employee was paid. That is normal and not an error.

Communicate W2 and 1099 Delivery with Staff

Employees and contractors will receive their tax documents by January 31 by mail. However, they can receive their tax documents early by opting into electronic delivery. All employees can download their W2s in Playground by following these instructions. Electronic W-2s are generally available in the employee portal by late January.

If your center switched to Playground mid-year from another payroll provider (Gusto, QuickBooks, ADP, Paychex, etc.): Let your staff know they will receive one W-2 from Playground that covers their full wages for the year. They should not use a W-2 from the previous provider for the same year. See the W-2s and 1099s: Admin Guide for details.

Staff must confirm their personal information by December 31.

Send an email or Playground message to all staff asking them to:

Log into the web version of Playground (not the mobile app)
Go to the Payroll tab and click Update Information
Confirm legal name, date of birth, SSN, home address, and electronic delivery preference
For step-by-step instructions, see W-2s and 1099s for Staff.

View and Download Staff W2s and 1099s

You can view every employee's W-2 from inside Playground, whether they chose paper or paperless delivery. If someone is having trouble getting to their document, you can download it and hand it to them.

When Documents Are Ready

What	When
W-2s and 1099s available in Playground	Mid-January
Paper copies placed in the mail	Week of January 18
Deadline for staff to have their copy	February 1, 2027

💡 February 1 rather than January 31 this year. The usual deadline is January 31, but it falls on a Sunday in 2027, so it moves to the next business day. Paper copies are postmarked by that date. Delivery time after that is up to the postal service.

Download All W-2s at Once

From your admin dashboard, navigate to the Payroll tab and click Tax.
Under Tax Documents, find Form W-2 Copy D for the year you need.
Click the three dots on the right side of the row and select View to download.

🚨 The download is one combined PDF, not separate files per person. Every employee's W-2 is in the same document. Before you hand anything out, split the PDF or print only the pages you need. Giving someone the whole file shares everyone's wage information.

Download One Employee's W-2

From your admin dashboard, navigate to the My School tab and click Staff.
Click the staff member's name to open their profile.
Click the Payroll tab, then the Tax documents sub-tab.
Find the Federal W-2 for the year you need.
Click the three dots on the right side of the row and select View to download.

How Terminated Employees Receive Their W-2

Everyone who earned wages from you in 2026 gets a W-2, including people who no longer work for you. You do not need to do anything special for them beyond making sure their details are right in checklist item 2.

Terminated staff are mailed a paper W-2 by default, to the address on file, even if they had opted into paperless delivery while they worked for you. This is deliberate, so they get their W-2 whether or not they still check their account.

They can also download it themselves. A disabled account still has access to payroll documents.

What a Former Employee Should Do

Log in at app.tryplayground.com using a web browser.
1. If their account is disabled, they will see a banner saying the account is restricted and to contact their administrator. This is expected and does not block access to payroll.
Navigate to the Payroll tab.
Click the Tax documents tab.
Click the three dots next to the Federal W-2 for the year they need.
Click the W-2 to download a copy.

💡 If a former employee cannot log in, they can reset their password from the login screen. You can also download their W-2 from their staff profile and send it to them directly.

🚨 Staff who left before you joined Playground still get a W-2 from us, as long as their pay history came over during setup. They do not need a Playground account. We mail theirs to the address on file.

Frequently asked questions

An employee was paid by check and we never processed it in payroll. Will they get a W-2?

Yes, as long as you tell us by December 14.

From your admin dashboard, navigate to the Payroll tab and open checklist item 3.
Send us the person's full legal name, the amount, and the date it was paid.
If they are not in your staff list, include their Social Security number and home address.
We will add the payment and it will appear on their W-2.

After December 14 we can still add it, but it means amending your tax filings for the affected quarters, and amendment fees apply. Report it now rather than in February.

An employee says their W-2 is wrong. What do I do?

Check the amounts first. W-2s show taxable wages, not gross pay, so pre-tax deductions like health insurance and 401(k) make the number smaller than expected. This is usually the answer.
If something is genuinely wrong, email [email protected].
Include the employee's name, exactly what needs to change, and your Check company ID.
We will confirm what is needed and whether a corrected W-2 (W-2C) has to be issued.

A misspelled name usually does not need a correction. The IRS matches W-2s by Social Security number, not by name spelling, so a minor variation will not affect your employee's tax filing. A wrong Social Security number does need fixing.

We switched to Playground mid-year. Which W-2 should employees use?

Employees should use only the Playground W-2.
Your pay history from the previous provider was imported during onboarding, so the Playground W-2 covers their full year.
If your previous provider also issued a W-2 for 2026, email [email protected] right away. Two W-2s for the same wages causes a filing problem that is better solved in January than in April.

A former employee is asking for their W-2. What do I tell them?

Their paper copy was mailed automatically to the address on file.
They can also log in at app.tryplayground.com on a web browser, even if their account is disabled, and download it from the Payroll tab.
If they cannot log in, they can reset their password from the login screen.
You can also download it from their staff profile and send it to them yourself.

Do contractors get a 1099 from Playground?

Yes. Contractors you paid through Playground receive a 1099-NEC on the same schedule as W-2s.
Confirm their details in checklist item 2: Social Security or tax ID number, whether they are an individual or a business, and a current address.
Contractors access their 1099 the same way employees access a W-2, from the Payroll tab on a web browser.

What happens if I miss the December deadlines?

Nothing is unfixable. Payroll can always be corrected.
After filings go out in mid-January, a change becomes a corrected W-2 (W-2C) rather than an edit. Your employee gets a second form and may need to wait or amend their own return.
Corrections affecting your tax returns are processed starting in February, and amendment fees apply.
The deadlines exist to keep your year end in the cheap, quick column. Email [email protected] as soon as you spot something, whatever the date.

W-2s and 1099s: Admin Guide — covers mid-year switches, corrected W-2s, churned accounts, and edge cases
W-2s and 1099s for Staff — employee-facing guide to downloading tax documents
Change or Update Company Payroll Details

Year-end Payroll Tasks