Contractor tax deadlines, as rules rather than dates.

Withheld income tax and both halves of FICA, deposited to the IRS.

Applies to

Anyone with employees.

The rule

Your deposit schedule — monthly or semiweekly — is set by your lookback period, not by choice, and the IRS tells you which one you are on. Monthly depositors deposit by the 15th of the following month. Semiweekly depositors deposit on Wednesday or Friday depending on which days the payroll fell in.

This is the one to get right above all the others. The withheld portion is trust fund money — it was deducted from an employee’s wages and is being held on the government’s behalf — and failing to pass it on can be assessed personally against an owner or anyone with cheque-signing authority. It does not necessarily go away if the company does.

You missed a payroll tax deposit

Quarterly payroll tax return, reconciling what you withheld and deposited.

Applies to

Anyone with employees.

The rule

Due the last day of the month following the end of each calendar quarter.

Filing the 941 is separate from depositing the money. Filing on time while depositing late does not fix a deposit problem, and the two carry different consequences.

Quarterly estimated income tax for the owner.

Applies to

Owners whose income is not fully covered by withholding — sole proprietors, partners, and S-corp owners whose salary withholding does not cover the pass-through income.

The rule

Four payments, due the 15th of April, June, September and the following January. The quarters are deliberately uneven; they are not three months apart.

A good year is what causes this problem. Profit rises, the estimates were set on last year’s figures, and the shortfall plus interest arrives with the return.

Annual federal unemployment (FUTA) return.

Applies to

Anyone with employees.

The rule

Due January 31 for the prior calendar year.

Wage statements, to your employees and to the Social Security Administration.

Applies to

Anyone with employees.

The rule

Due to employees and to the SSA by January 31. Both copies, same date — the later filing date that used to apply to the government copy is long gone.

Reporting payments to subcontractors and other non-employees.

Applies to

Anyone who paid an unincorporated subcontractor or service provider more than the reporting threshold during the year.

The rule

Due to the recipient and to the IRS by January 31 — unlike most other information returns, there is no later date for the IRS copy.

The trade’s specific trap: you cannot file these without a W-9 from every sub, and chasing a W-9 in January from someone who worked for you in March is how this deadline gets missed. Collect the W-9 before the first payment, not before the deadline.

The 1099-NEC deadline

Partnership and S-corporation income tax returns.

Applies to

Partnerships, LLCs taxed as partnerships, and S-corporations.

The rule

Due the 15th day of the third month after the end of the tax year. An extension moves it six months.

A month earlier than most owners expect, because the K-1s it produces have to reach the partners before their personal returns are due.

The deadline is close and the books are not ready

Personal and C-corporation income tax returns.

Applies to

Sole proprietors filing Schedule C, individual owners, and C-corporations.

The rule

Due the 15th day of the fourth month after the end of the tax year. An extension moves it six months.

An extension extends the time to FILE, never the time to PAY. Tax owed is still due at the original date, and interest runs from there regardless of the extension.