Massachusetts estimated tax payments for the self-employed and small firms

Key takeaways

• The Massachusetts Department of Revenue (DOR) requires estimated tax payments from anyone who expects to owe more than $400 in Massachusetts income tax on income not subject to withholding.
• The 2026 Form 1-ES instructions set four equal installments, due April 15, 2026, June 15, 2026, September 15, 2026 and January 15, 2027.
• Under M.G.L. c. 62B, s. 14, the required annual payment for an individual is the lesser of 80% of the current year’s tax or 100% of the tax shown on the prior year’s return.
• A corporation that expects its Massachusetts corporate excise to exceed $1,000 pays estimates on Form 355-ES, split 40%, 25%, 25% and 10%.
• The Internal Revenue Service (IRS) runs a separate federal system on Form 1040-ES, with a $1,000 threshold for individuals and a 90% current-year test.

Massachusetts estimated tax payments are installments of state income tax or corporate excise that you send to the Department of Revenue during the year, because no employer is withholding the tax for you. If you are a freelancer, sole proprietor, partner or small-firm owner in Boston or anywhere else in the Commonwealth, the short answer is this: once you expect to owe more than $400 in Massachusetts tax on income with no withholding, DOR expects four payments a year on Form 1-ES. The rule is a state rule. Neither the City of Boston nor any other city or town collects an income tax.

The sections below cover who has to pay, the 2026 due dates, how much is enough to avoid an underpayment charge, how to send the money through MassTaxConnect, the separate schedule for corporations, the exceptions, and how the federal Form 1040-ES rules differ.

Who has to make Massachusetts estimated tax payments?

Massachusetts estimated tax payments are required from residents and nonresidents who expect to owe more than $400 in tax on income not subject to withholding, according to the Department of Revenue’s estimated tax page (last updated January 29, 2026). DOR lists these kinds of income as examples:

• Business or partnership income
• Salaries and wages from a job with no Massachusetts withholding
• Dividends and interest
• Capital gains
• Rental income

The 2026 Form 1-ES instructions add that members of pass-through entities and people receiving unemployment compensation may also have to pay. A sole proprietor in Dorchester and a partner in a Cambridge firm are in the same position: nobody withholds on their share of the profit, so each pays through Form 1-ES. The Form 1-ES worksheet for 2026 applies a 5% rate to most income, including business income, and an 8.5% rate to short-term capital gains.

When are Massachusetts estimated tax payments due in 2026?

Massachusetts estimated tax payments for individuals are due in four equal installments on April 15, 2026, June 15, 2026, September 15, 2026 and January 15, 2027, according to the 2026 Form 1-ES instructions. You can also pay the full year’s estimate by April 15, 2026. Corporations follow an earlier schedule, published on DOR’s tax due dates and extensions page.

Installment	Individuals (Form 1-ES)	Corporations (Form 355-ES)
First	April 15, 2026	March 16, 2026
Second	June 15, 2026	June 15, 2026
Third	September 15, 2026	September 15, 2026
Fourth	January 15, 2027	December 15, 2026

One conflict needs a mention. As of November 13, 2026, two DOR web pages list the second individual installment as June 16, 2026, while the 2026 Form 1-ES and the statute both say June 15. Treat June 15 as the date and confirm with DOR if a day matters to you.

When a due date falls on a weekend or legal holiday, the Form 1-ES instructions let you pay on the next business day. Fiscal-year filers pay on the 15th day of the fourth, sixth and ninth months of the fiscal year and the 15th day of the first month of the next one. DOR had not posted 2027 vouchers when this guide was checked.

How much do you have to pay to avoid an underpayment charge?

The amount you have to pay to avoid an underpayment charge is the “required annual payment” defined in M.G.L. c. 62B, s. 14: the lesser of 80% of the tax shown on your return for the year, or 100% of the tax shown on your return for the preceding year, if that return covered 12 months. Each installment is 25% of that amount.

The charge for falling short is an addition to tax, figured on each late or short installment at the interest rate set under M.G.L. c. 62C, s. 32, without daily compounding. It runs from the installment’s due date until you pay, or until the return’s due date if that comes first. Individuals work out the amount, and check whether an exception applies, on Form M-2210, Underpayment of Massachusetts Estimated Income Tax. DOR also has an M-2210 calculator on MassTaxConnect.

How do you make a Massachusetts estimated tax payment?

You make a Massachusetts estimated tax payment either online through MassTaxConnect, DOR’s web portal for filing and paying state taxes, or by mailing a Form 1-ES voucher with a check. The steps for an individual are:

1. Fill in the Estimated Tax Worksheet in the 2026 Form 1-ES instructions to project your income, deductions and tax for the year.
2. Subtract the Massachusetts withholding you expect. If the result is less than $400, the worksheet says no estimated payments are required.
3. Divide the balance into four installments.
4. Pay each installment at MassTaxConnect, or mail a voucher and a check payable to the Commonwealth of Massachusetts to the Massachusetts Department of Revenue, PO Box 419540, Boston, MA 02241-9540.
5. Keep a record of each payment. You can check your totals on MassTaxConnect or by calling DOR at (617) 887-6367.

Paper is not open to everyone. DOR’s e-filing and payment requirements page says corporations must make all payments electronically, and every taxpayer subject to the 4% surtax must file and pay electronically. If your income changes during the year, redo the worksheet and adjust the remaining installments. DOR states that MassTaxConnect does not accept a prior year’s estimated payment after January 15.

How do estimated payments work for Massachusetts corporations?

Estimated payments for Massachusetts corporations apply to every corporation that reasonably estimates its corporate excise at more than $1,000 for the taxable year, according to DOR’s corporate excise estimated payments page. The corporate excise is the Massachusetts tax on corporations under M.G.L. c. 63. A corporation pays the estimate in full by the 15th day of the third month of its taxable year, or in four installments on the 15th day of the third, sixth, ninth and twelfth months.

The installments are not equal. Most corporations pay 40%, 25%, 25% and 10% of the required annual payment. Corporations use Form 355-ES and pay electronically. Under M.G.L. c. 63B, s. 3, the required annual payment is generally the lesser of 90% of the current year’s tax or 100% of the prior year’s tax. The prior-year option is not available if the prior year was shorter than 12 months or the prior return showed no tax. Large corporations, as the Internal Revenue Code defines them, can use the prior year only for the first installment.

When does the usual rule not apply?

The usual rule does not apply in several cases written into M.G.L. c. 62B, s. 14 and DOR’s guidance. The main ones are:

• Small balances: no addition to tax applies if your tax for the year, after credits, is less than $400.
• No tax last year: no addition applies if you had no Massachusetts tax liability for the preceding 12-month taxable year and were a Massachusetts inhabitant for all of it.
• Farmers and fishermen: the 80% test drops to two-thirds (66.67%), and no addition applies if they file and pay in full by March 1 of the following year.
• New corporations: a corporation in its first full taxable year with fewer than 10 employees pays 30%, 25%, 25% and 20%, according to DOR.
• Hardship: the Commissioner of Revenue may waive the addition after a casualty or disaster, or for a taxpayer who retired after age 62 or became disabled and had reasonable cause.

One rule works against you. DOR says no safe harbor applies to first-year filers of fiduciary, corporate trust or nonprofit returns. High earners have an extra item to count: the 4% surtax applies to taxable income over $1,107,750 for tax year 2026, and DOR says you must include it when you figure your required estimate.

How do federal estimated taxes differ from the Massachusetts rules?

Federal estimated taxes differ from the Massachusetts rules in the threshold, the percentage test and the agency that collects them. The IRS says on its estimated taxes page that individuals, including sole proprietors, partners and S corporation shareholders, generally pay estimated tax if they expect to owe $1,000 or more when they file. Corporations pay if they expect to owe $500 or more. Individuals use Form 1040-ES.

The federal test is 90% of the current year’s tax or 100% of the prior year’s tax, whichever is smaller. The IRS estimated tax FAQ raises the prior-year figure to 110% if your adjusted gross income was more than $150,000. Massachusetts uses 80% and has no 110% tier in c. 62B, s. 14. The federal due dates for individuals (April 15, June 15, September 15 and January 15 of the following year) match the Massachusetts ones. A federal payment does not count toward your Massachusetts estimate, and a payment to DOR does not count with the IRS. You make two sets of payments.

What should you recheck before you act?

The figures below were checked on November 13, 2026. Confirm each one with the agency named before you rely on it.

• 2027 due dates: DOR issues a new Form 1-ES each year. Look for the 2027 vouchers and dates on DOR’s estimated tax page on mass.gov.
• The June 2026 date: DOR’s web pages showed June 16, 2026 and the 2026 Form 1-ES showed June 15, 2026.
• The $400 and $1,000 thresholds and the 80% and 90% tests: confirm in M.G.L. c. 62B, s. 14 and c. 63B, s. 3 on malegislature.gov.
• The 4% surtax threshold: $1,107,750 is the 2026 figure and it is adjusted each year. Check DOR’s surtax page for 2027.
• The interest rate on underpayments: DOR publishes the current rate under M.G.L. c. 62C, s. 32. This guide does not quote it.
• Federal amounts: confirm the $1,000 and $500 thresholds and the 110% rule on irs.gov or in IRS Publication 505.

This guide is general information, not legal or tax advice. Rules and fees change; confirm the current requirements with the agency named before you file or pay.

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