Payroll taxes have multiple deadlines throughout the year. There are deposit deadlines for the taxes you withhold, quarterly filing deadlines for Form 941, and annual deadlines for unemployment tax and W-2s. Missing any of them triggers penalties that compound quickly.

Federal payroll tax deposits follow one of two schedules based on your total liability during a lookback period. The IRS looks at your payroll taxes from July 1 through June 30 of the prior year. If you reported $50,000 or less, you’re a monthly depositor. Your deposits are due by the 15th of the following month. So taxes withheld from January paychecks are due by February 15.

If your lookback period liability exceeded $50,000, you’re on a semi-weekly schedule. Taxes from paychecks dated Wednesday through Friday are due the following Wednesday. Taxes from paychecks dated Saturday through Tuesday are due the following Friday. This is tighter than monthly but gives you a few days of breathing room.

New employers without a full lookback period start as monthly depositors. If you accumulate $100,000 or more in tax liability on any single day, you must deposit by the next business day regardless of your normal schedule.

Form 941 is due quarterly: April 30 for Q1, July 31 for Q2, October 31 for Q3, and January 31 for Q4. This form reports wages paid, taxes withheld, and employer Social Security and Medicare taxes. You file even if you already deposited all the taxes. The form reconciles what you owe with what you paid.

Form 940 for federal unemployment tax is due January 31 each year. If your FUTA liability exceeds $500 in any quarter, you need to make quarterly deposits. Most small employers make one annual deposit and file by January 31.

W-2s must go to employees and to the Social Security Administration by January 31. This deadline has no extension for small businesses. Late W-2s mean penalties per form that add up fast when you have multiple employees.

Massachusetts employers have state withholding requirements on top of federal. Deposit frequency depends on your annual liability. Employers owing less than $100 annually can pay when filing the annual return. Most small businesses with a few employees fall into monthly or quarterly deposit schedules. The state also requires Form M-941 quarterly, similar to the federal 941.

Penalties for late deposits start at 2% if you’re one to five days late and escalate to 15% for deposits more than ten days past due. Late quarterly returns carry their own penalties plus interest. The IRS and Massachusetts Department of Revenue both assess penalties automatically. You won’t get a warning before they hit your account.

The easiest way to avoid missed deadlines is to use managed payroll that handles deposits and filings automatically. Payroll software calculates the liability and initiates deposits on schedule. A small business bookkeeping service can review your payroll compliance quarterly to catch problems before they become expensive.

Most payroll tax problems come from cash flow issues, not ignorance of deadlines. Business owners know deposits are due but don’t have the money. Using withheld taxes to cover other expenses is tempting but never works out. Those taxes belong to the government and borrowing them comes with penalties, interest, and potential personal liability that follows you even if the business closes.