What Did I Forget? A 2-Minute CT Small-Business Tax Checker

A free checker for Connecticut small-business owners, freelancers and gig workers. It flags deductions, deadlines and filings worth a second look.

For general education only. Not tax, legal, insurance, or investment advice, and not a promise of any result. Tax rules and due dates change, so confirm with the IRS (irs.gov), the CT Department of Revenue Services (portal.ct.gov/DRS) or your town before you act, and ask your tax preparer about your own situation.

About 2 minutes, up to 17 quick questions. Answer yes, no or not sure. You'll get a checklist of deductions, deadlines and filings that may be worth checking with your tax preparer. Your answers stay in your browser.

1. What kind of business do you have?
Do you use part of your home regularly and only for business?
Do you drive your own car for business (not just your commute)?
Have you made quarterly estimated tax payments (federal and CT) this year?
Do you expect $400 or more in net self-employment earnings this year?
Has the business decided whether to elect the CT pass-through entity tax this year?
Do you pay yourself a salary through payroll from the S corporation?
Do you contribute to a retirement plan for your business income (SEP IRA, SIMPLE IRA, solo 401(k))?
Do you pay for your own health insurance, with no employer plan available to you?
Did you pay any contractor (not an employee) $2,000 or more this year for services?
Do you get paid through payment apps or online marketplaces?
Do you sell products, or services that might be taxable, to customers in Connecticut?
Is your business a Connecticut LLC or corporation?
Does your business own equipment, furniture or fixtures in a CT town?
Do you use a business name that isn't your own name or your LLC's exact name?
Do you have W-2 employees?
Do you keep business money in a separate account and save receipts?

Your "worth checking" list

    These are items worth checking with your tax preparer. They're based only on your yes / no answers, so they aren't a finding that anything applies to you or that anything is due.

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    What this checker looks at

    • Deductions people often miss: home office, business mileage, self-employed health insurance, retirement plan contributions and the QBI deduction.
    • Federal and CT deadlines: quarterly estimates, 1099-NEC filings, the CT LLC annual report and the business personal property declaration.
    • Connecticut-specific items: the elective pass-through entity tax, the sales and use tax permit, trade name certificates and payroll registrations.

    Want the dates in your inbox? Sign up for free tax deadline reminders. Starting a new business? Try the CT business launch wizard.

    Frequently asked questions

    Does this checker tell me what I owe or what I qualify for?

    No. It only lists items that may be worth checking, based on your yes / no answers. Whether a deduction or filing applies depends on your full situation, so ask your tax preparer.

    Is the Connecticut pass-through entity tax mandatory?

    Not anymore. For tax years starting on or after January 1, 2024, the CT pass-through entity tax is elective. A partnership or S corporation chooses it each year on a timely filed Form CT-1065/CT-1120SI, and the election can't be changed later.

    What changed for Form 1099-NEC in 2026?

    For payments made in 2026, the IRS reporting threshold for Form 1099-NEC rose from $600 to $2,000. Forms for 2026 payments are due February 1, 2027, because January 31 is a Sunday.

    Do I need a CT sales tax permit if I only sell a little?

    Connecticut DRS says anyone who sells goods or taxable services in the state needs a Sales and Use Tax Permit before making sales, regardless of how many sales they make. Occasional casual sales by someone not in business are an exception.

    Is my checklist saved or shared?

    Your answers stay in your browser. If you ask us to email the checklist, we send your email, optional first name and the names of the flagged items to our email provider so we can send it.

    Sources (Checked November 3, 2026)

    For general education only. Not tax, legal, insurance, or investment advice, and not a promise of any result. Tax rules and due dates change, so confirm with the IRS (irs.gov), the CT Department of Revenue Services (portal.ct.gov/DRS) or your town before you act, and ask your tax preparer about your own situation.

    Found a few items worth checking? We can help you sort them out.

    Request a quoteBook a 15-minute call

    Or call (475) 242-7941. Services are priced by quote.

    Enhance Finance is a small-business finance practice serving Connecticut.