Calendar (Confirm Current IRS Publication)

Form Federal due (2025 forms filed 2026) Notes
W-2 Copy A to SSA Feb 2, 2026 BSO/W-2c for corrections
1099-NEC Feb 2, 2026 Independent contractor comp
1099-MISC Mar 2, 2026 e-file Rents, other income
1099-K Mar 31 / state varies Confirm threshold + state rules
State 1099/W-2 Jan 31–Mar 31 varies Many states require direct filing

Dates shift with weekends and IRS updates. Confirm Publication 1220 and SSA specs before filing week.

Pair with 1099 vs W-2, Payroll, Year-End Close, and Year-End Tax Planning.

60-Day Prep Plan

Nov: scrub W-9s, TIN-match, verify addresses, lock vendor 1099 flags — see Bookkeeping. Dec: freeze AP cut-off, true-up bonuses, reconcile payroll to GL — see Multi-State. Jan: e-file, furnish recipient copies, reconcile filings to GL (zero plugs), file state copies.

Enforce roles per QuickBooks vs Xero and retain per Record Retention.

Penalty Tiers (Framework)

  • Filed ≤30 days late: lower per-return amount.
  • Filed after 30 days but by Aug 1: mid-tier.
  • Filed after Aug 1 or not filed: high-tier.
  • Intentional disregard: flat high amount per return, no cap.

Add state penalties and interest. Small counts still hurt — prevention is cheaper than correction.

Correction Workflow

  1. Identify scope: returns, amounts, TINs.
  2. File corrected federal + state promptly; issue W-2c/1099 corrected.
  3. Amend payroll returns (941-X) if withholding affected.
  4. Fix vendor master and payroll codes; memo root cause for Audit Procedures.

Worked Example: 40 Contractors, 3 Missing W-9s, 1 Wrong Box

December scrub finds: 38 valid W-9s on file, 2 missing, 1 LLC taxed as S-corp incorrectly flagged for 1099-NEC, and $18,000 in rent mis-coded to contractor expense (belongs on 1099-MISC, not NEC). Fixes before filing:

Issue Fix Penalty avoided
2 missing W-9s Backup withholding notice + TIN solicitation log (documents reasonable cause) $60–$310 per return tier
S-corp LLC flagged Remove from NEC file; confirm via W-9 entity type False filing + correction cycle
$18k rent on NEC file Move to MISC, Box 1 Mismatched-form notice and CP2100 cycle

The TIN solicitation log is the unsung hero: first notice + second notice documented means missing-TIN penalties drop to reasonable-cause relief instead of intentional-disregard territory. Start it in November, not January 30th.

1099-K and State Threshold Chaos (2026 Reality)

Federal 1099-K thresholds moved repeatedly ($20k/200 → $5k → $2k proposals); states never waited. Massachusetts, Vermont, Virginia, and others enforce $600 state thresholds with direct filing — meaning you can owe zero federal K forms and dozens of state ones. Process:

  1. Pull payment-settlement reports by state (Stripe/PayPal state breakdowns exist — use them).
  2. Track monthly against each state’s threshold, not just federal — the same nexus-tracker discipline as SALT and SaaS Nexus.
  3. File state copies directly where required (many states don’t accept FIRE-only; they want portal filing).

Calendar state 1099-K deadlines separately from federal — they cluster in the same Jan 31–Mar 31 window when the team is already at capacity. Assign the state matrix to one owner in the Year-End Close calendar.

TIN Matching That Actually Works

IRS TIN Matching (real-time or bulk) beats eyeballing W-9s: submit name/TIN pairs in November, fix mismatches with vendors while there’s time, and retain the match confirmations. Common failures: DBA vs legal name on line 1 (match line 1 exactly), hyphenated names truncated by AP entry, and single-member LLCs showing the owner’s SSN under the entity EIN. Each corrected mismatch in November is a CP2100 notice avoided in August. Pair with Bookkeeping master-data hygiene and file the match log with the PBC packet.

FAQ

Do we file 1099 for LLCs?

Generally 1099-NEC for individuals, partnerships, and LLCs taxed as such for $600+ services; corporations usually exempt except attorney/medical. Confirm with current instructions and W-9.

What about state 1099-K?

States diverge on thresholds and direct filing. Track monthly — see SALT and SaaS Nexus.

Next Steps

  1. Pull 1099 population from GL this week and scrub W-9s.
  2. Calendar e-file TCC/BSO access and state logins.
  3. Reconcile filings to Month-End Close binder before submission.