The Year-End Close: Five Dates That Decide January
January is not busy because of January. It is busy because of what was left undone in October and November, and this year there is more of it than usual: the first W-2 carrying the new tip and overtime boxes, a Massachusetts PFML re-code, and a contractor reporting threshold that moved for the first time in decades.
None of it is difficult. All of it is time-bound, and most of it depends on having books that are already closed rather than books you are closing while the deadline runs.
Here are the five dates, what each one actually requires, and which of them you can still comfortably prepare for.
Key Takeaways
- 31 December — equipment must be placed in service, not merely ordered, to count for this year.
- 1 January — the Massachusetts PFML employer contribution moves from medical leave to family leave. Same money, different bucket.
- 15 January — fourth 2026 estimated tax payment.
- 1 February — Form 1099-NEC is due, at the new $2,000 threshold. The same date lets you skip the 15 January payment if you file and pay in full.
- The W-2 you file in January is the first one carrying box 12 codes TP and TT and the box 14b occupation code.
The five dates
| Date | What it is | Prepare it by |
|---|---|---|
| 31 Dec 2026 | Equipment placed in service to count for 2026 | Early December — installers, not suppliers, are the constraint |
| 1 Jan 2027 | MA PFML employer share moves to family leave | Before the first January payroll run |
| 15 Jan 2027 | Fourth 2026 estimated tax payment | Needs a December close to size correctly |
| 1 Feb 2027 | Form 1099-NEC due, threshold now $2,000 | W-9s collected now, totals run in early January |
| 1 Feb 2027 | File the 2026 return and pay in full → skip 15 Jan | Only possible if the books close in January |
What is new this year, and what is not
Three of these are the ordinary rhythm. Two are not, and the new ones are where mistakes will cluster.
New: the W-2 boxes. The form you file in January is the first to carry box 12 code TP for cash tips reported to the employer, code TT for qualified overtime, and box 14b for the Treasury Tipped Occupation Code. The commonest error will be code TT, because only the premium half of time-and-a-half belongs in it. If your payroll system has been accumulating the full overtime payment all year, the figure is already wrong and January is late to find out. The detail is in the 2026 W-2 walkthrough.
New: the 1099 threshold. $600 became $2,000 for 2026. Fewer forms, but the threshold is annual and cumulative, so you cannot know who crosses it until the year closes — which is why the W-9 practice does not change.
Not new, but re-coded: PFML. The totals are identical in 2027 — employee 0.46%, employer 0.42% — and only the bucket the employer’s share funds changes. That is exactly the kind of change that passes a payroll report unnoticed, because the numbers reconcile either way. The 2027 rates are published.
The dependency nobody puts on the list
Four of the five dates above assume one thing that is never itself a deadline: that December can be closed in the first half of January.
If the accounts are reconciled monthly, December is a two-week job and everything downstream becomes possible — you can size the 15 January payment properly, or skip it by filing early; you can total vendor payments per payee and know who needs a 1099; you can see whether a December equipment purchase actually helps.
If the accounts have not been reconciled since the summer, none of those choices exist. The estimated payment becomes a guess, the 1099 run becomes a reconstruction, and the return gets filed in March with figures that were still moving in February.
That is the honest argument for keeping the books current, and it is not about tidiness. It is that a closed set of books gives you options in January and an open set takes them away. If yours are behind, catch-up work takes longer in December than it does now.
What to do in the next two weeks
- Run one overtime payslip and confirm the figure earmarked for box 12 code TT is the premium only, not the whole payment.
- Total 2026 vendor payments by payee and chase W-9s from anyone near $1,500 — they are the ones a December invoice pushes over.
- Confirm install dates for any equipment you intend to deduct this year.
- Ask your payroll provider, in writing, what they are changing on 1 January for PFML and whether their 2026 W-2 output populates TP, TT and 14b.
- Decide whether a January filing is realistic. If it is, 1 February replaces 15 January and you make one payment instead of two.
Point 4 is worth doing by email rather than phone. “We’re compliant” is not an answer to that question, and you want the answer in a form you can point at later.
How this was checked
The 1099-NEC threshold and the January 31 filing deadline including the weekend rule come from the IRS Instructions for Forms 1099-MISC and 1099-NEC. The estimated tax dates and the February 1 alternative come from IRS Form 1040-ES (2026). The PFML figures come from the Massachusetts DFML contribution rates page as updated on 1 October 2026. The W-2 codes come from the IRS 2026 General Instructions for Forms W-2 and W-3.
February 1, 2027 is a calculated date rather than a printed one: both the 1099 deadline and the estimated tax alternative are stated as January 31 and February 1 respectively in the source documents, and January 31, 2027 is a Sunday.
Green Books Inc. is a bookkeeping practice — Certified Bookkeeper (CPB), IRS Authorized e-File Agent, and Notary Public. This is general information about published rules, not tax advice, and the dates that apply to you depend on your entity type and filings.
Frequently asked questions
We are a sole proprietor with no employees. Which of these matter?
The 15 January estimated payment, the 1 February alternative, and the 1099-NEC obligation if you pay contractors $2,000 or more. The PFML and W-2 items are employer obligations and do not reach you until you hire.
Our payroll is outsourced. Do we still need to check the W-2 boxes?
Yes. The filing is made under your EIN and the obligation is yours. A provider that populates the fields correctly makes this a non-issue; one that does not leaves you filing incorrect returns in your own name, and the time to discover which you have is now.
What happens if we miss the 1 February 1099 deadline?
Penalties scale with how late the filing is and with the size of the business, so the cost of being a week late is not the cost of being three months late. The more useful framing is that the deadline is only hard to hit when the W-9s were not collected during the year.
Is there anything due in December itself?
No filing, but 31 December is the cut-off for equipment to be placed in service and for most actions that affect the 2026 figures. December is a deadline for doing things, not for submitting them — which is why it tends to be underestimated.
Two weeks of work, spread over two months
Nothing on this list takes long. What makes January hard is attempting all of it in the same fortnight, with a December close running underneath it.
If you would like your year-end mapped against these dates — or your books brought current so a January filing is actually on the table — book a consultation. The reporting side is payroll, and the return itself is tax preparation.