Which federal tax dates catch small businesses out?
The quarterly ones, and the cluster at the end of January. For the 2026 tax year, As of Oct 2026:
- Estimated tax on Form 1040-ES, if you will owe $1,000 or more after withholding and credits: April 15, June 15 and September 15, 2026, and January 15, 2027 (IRC sec. 6654).
- Payroll tax deposits: monthly, by the 15th of the next month, or semiweekly, depending on your lookback period. A late deposit costs 2% up to 5 days late, 5% at 6 to 15 days and 10% after that, or 15% if still unpaid 10 days after an IRS notice (IRC sec. 6656).
- Form 941, the quarterly payroll return: April 30, July 31, October 31 and January 31. Form 940 and Forms W-2 to staff and the Social Security Administration: January 31.
- Form 1099-NEC to each contractor you paid $2,000 or more in 2026, and to the IRS: January 31.
A federal due date on a Saturday, Sunday or legal holiday moves to the next business day (IRC sec. 7503), so the 2026 Forms W-2 and 1099-NEC are due Monday, February 1, 2027.
Which state filings are easy to miss?
Sales tax returns and the yearly entity filing, because each state sets its own dates. As of Oct 2026:
- Sales tax returns, on the frequency your state assigns: monthly Texas filers by the 20th of the next month; quarterly New York filers by the 20th of March, June, September and December; Florida returns are due on the 1st and late after the 20th. See when you must collect in other states.
- Florida: an LLC's annual report between January 1 and May 1 (Fla. Stat. sec. 605.0212(3)), with a $138.75 fee and a $400 late fee after May 1 (Florida Division of Corporations).
- Texas: the franchise tax report by May 15. At or below the no-tax-due threshold ($2.65 million for 2026 and 2027 reports) you owe no franchise tax but still file the Public Information Report or Ownership Information Report (Tax Code secs. 171.002(d), 171.202 and 171.203).
- California: an LLC pays the $800 annual tax by the 15th day of the 4th month of its tax year, April 15 for a calendar year, even with no income (Rev. and Tax. Code sec. 17941).
Which licenses and certifications need renewing?
Many cities require a business license or tax registration, even for a home-based business, and trades add state licenses, bonds and certifications, each on its own cycle. Examples, As of Oct 2026:
- California contractors: the CSLB license renews every 2 years (Bus. and Prof. Code sec. 7140) and carries a $25,000 contractor's bond (sec. 7071.6). If your qualifying individual leaves, the license must be requalified within 90 days (sec. 7068.2).
- Plumbers: each plumbing, gas and electrical license with its continuing education, contractor bonds and backflow tester certifications (see plumbing, heating and electrical).
- Painters and renovators on lead-safe (RRP) work: EPA firm certification lasts 5 years; a Certified Renovator refreshes every 5 years with hands-on training, or every 3 years if the refresher had no hands-on training (40 CFR 745.89 and 745.90).
- Landscapers: pesticide applicator licenses and continuing education credits by the state's date (see landscaping licenses).
- California cleaning companies: Property Service Workers Protection Act registration every year (Lab. Code secs. 1420 to 1434).
If you keep OSHA injury logs, post the Form 300A summary from February 1 to April 30 (29 CFR 1904.32(b)(6)). See starting a job with the right license and permits.
Which insurance renewals matter most?
Workers' compensation first, because in most states it is the law, not only a contract term. Rules vary by state; As of Oct 2026:
- California and New York require it from the first employee (Cal. Lab. Code sec. 3700; N.Y. Workers' Comp. Law sec. 10).
- Florida requires it from 1 employee in construction and from 4 in other industries (Fla. Stat. sec. 440.02). Working without it brings a stop-work order and a penalty of twice the premium you should have paid (sec. 440.107(7)).
- Texas lets private employers opt out as nonsubscribers, who lose their common-law defenses in an injury suit (Tex. Lab. Code sec. 406.033).
Add general liability, commercial auto and bond renewals, the workers' comp audit after each policy year, and the expiry of every certificate of insurance you hold for your subs.
What happens if something lapses?
Usually more than the renewal would have cost. Examples, As of Oct 2026:
- In California, contracting without a license is a misdemeanor, an unlicensed contractor cannot sue to be paid, and the customer can recover what it paid (Bus. and Prof. Code secs. 7028 and 7031).
- A Texas entity that skips its franchise tax or information report can have its right to do business forfeited (Tax Code secs. 171.251 and 171.2515).
- Payroll taxes withheld from staff are trust funds: unpaid, the IRS can assess 100% of them against any responsible person who willfully failed to pay (IRC sec. 6672).
How do I set up a simple tracking system?
One list, one owner per line, and reminders well ahead. A spreadsheet or shared calendar works if each line carries:
- What it is, its number and who issues it: the IRS, the state, a licensing board, the city or an insurer.
- The due or expiry date, from the license, policy or agency calendar, confirmed with the agency on the day you enter it.
- What renewal takes: a fee, continuing education hours, an inspection, a bond or proof of insurance.
- Who owns it, with reminders 60 and 30 days ahead, and where the proof goes once it is done.
Rebuild it each January and whenever you hire or sell into a new state. Ask your CPA to check the tax lines, and a licensing attorney before working in a new state.
How Greymill helps
Rules & Licensing covers licensing, inspections, safety and data rules, and the dates you must not miss: it puts every filing date for your business and trade in your overnight brief, before it is due. Greymill loads your trade's rules when you sign up, and you give your state once.
Ask Anything writes the brief overnight: the next deadline, the cash to watch and three tasks for today, in the app every morning and by email at 7am on Mondays and Fridays.
Greymill files nothing on your behalf, owes no professional duty, and says when your CPA or an attorney must sign something off. QuickBooks or Xero change only when you press Approve, nothing is sent unless you press Send, and conversations are not used to train AI. Try it free for 7 days on full Scale access, no card needed; plans from $130 a month plus tax. See pricing and how it works.
Questions owners ask
When are quarterly estimated taxes due?+
For the 2026 tax year: April 15, June 15 and September 15, 2026, and January 15, 2027, on Form 1040-ES, if you will owe $1,000 or more after withholding and credits. A date on a weekend or legal holiday moves to the next business day. As of Oct 2026.
How often does a California contractor license renew?+
Every 2 years (Bus. and Prof. Code sec. 7140), with a $25,000 contractor's bond. An unlicensed contractor in California cannot sue to be paid. As of Oct 2026.
When is a Florida LLC annual report due?+
Between January 1 and May 1 each year, starting in the calendar year after the LLC's articles take effect (Fla. Stat. sec. 605.0212(3)). The fee is $138.75, and the Division of Corporations adds a $400 late fee after May 1. As of Oct 2026.
Do I need workers' comp for one employee?+
In California and New York, yes. In Florida, yes in construction, and from 4 employees in other industries. Texas private employers may opt out as nonsubscribers but lose common-law defenses in injury suits. Rules vary by state. As of Oct 2026.
Sources
- IRC sec. 6654, checked Oct 2026
- IRC sec. 7503, checked Oct 2026
- IRS Publication 15 (2026); IRC secs. 6656 and 6672, checked Oct 2026
- IRS, Instructions for Form 941, when to file, checked Oct 2026
- IRS, 2026 Instructions for Forms 1099-MISC and 1099-NEC, checked Oct 2026
- Texas Comptroller, sales and use tax due dates, checked Oct 2026
- New York Tax Department, 2026 filing dates, checked Oct 2026
- Florida Department of Revenue, sales and use tax, checked Oct 2026
- Florida Division of Corporations, annual report fees and late fee, checked Oct 2026
- Fla. Stat. sec. 605.0212(3), checked Oct 2026
- Texas Comptroller, franchise tax, checked Oct 2026
- Tex. Tax Code secs. 171.002, 171.202, 171.203, 171.251 and 171.2515, checked Oct 2026
- California FTB, LLC annual tax, checked Oct 2026
- Cal. Bus. and Prof. Code sec. 7140, checked Oct 2026
- Cal. Bus. and Prof. Code secs. 7068.2 and 7071.6, checked Oct 2026
- Cal. Bus. and Prof. Code secs. 7028 and 7031, checked Oct 2026
- 40 CFR 745.89 and 745.90, checked Oct 2026
- California Labor Commissioner, janitorial registration; Lab. Code secs. 1420 to 1434, checked Oct 2026
- 29 CFR 1904.32(b)(6), checked Oct 2026
- Cal. Lab. Code sec. 3700, checked Oct 2026
- N.Y. Workers' Comp. Law sec. 10, checked Oct 2026
- Fla. Stat. sec. 440.02, checked Oct 2026
- Fla. Stat. sec. 440.107(7), checked Oct 2026
- Tex. Lab. Code sec. 406.033, checked Oct 2026
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