For Marylanders, Individuals, Businesses, Payroll Filers, and Fiduciaries
May usually feels quieter than April, but it is still an important tax month—especially for employers and small business owners. This guide walks through the key May 2026 IRS and Maryland deadlines, explains who each one applies to, and highlights practical steps to help you avoid penalties and stay organized.
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Why May deadlines matter
After the pressure of April filing season, many taxpayers assume May is a breather. In some ways, it is. Most individuals do not have a regular federal or Maryland income tax return due in May.
But for employers, business owners, and anyone responsible for payroll or state tax filings, May can still be expensive if it gets overlooked. It is a month that often includes:
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The good news is that May deadlines are manageable when you know which ones actually apply to you.
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May 2026 Calendar (IRS and Maryland Deadlines that may apply)
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Mon
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Tue
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Wed
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Thu
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1
IRS semiweekly payroll deposit
Form 730 excise tax return/payment for April (if applicable)
FUTA deposit for Q1 if liability exceeds threshold
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3
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5
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6
IRS semiweekly payroll deposit
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IRS semiweekly payroll deposit
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11
IRS April tip reporting to employer
Form 941 (Q1) if deposits were timely and paid in full
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12
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13
IRS semiweekly payroll deposit
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14
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15
IRS semiweekly payroll deposit
IRS monthly payroll deposit for April wages
Certain exempt organization Form 990 series / Form 8868 filings
MD monthly withholding return/payment for April
MD quarterly withholding return/payment for Q1 if quarterly filer
MD corporate estimated tax installment if fiscal-year due date falls in May
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17
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IRS semiweekly payroll deposit
MD monthly sales & use tax return/payment for April
MD quarterly sales & use tax return/payment for Q1 if quarterly filer
Other MD monthly business taxes due on the 20th based on account type
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IRS semiweekly payroll deposit
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IRS semiweekly payroll deposit
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IRS semiweekly payroll deposit
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Legend: IRS / Federal deadline Maryland deadline
Applicability note: Not every item applies to every filer. Some deadlines depend on filing frequency (monthly, quarterly, annual, or accelerated), entity type, or whether a specific tax account is active.
Recurring rules to watch throughout May: Maryland accelerated withholding generally applies within three business days after payroll for employers that meet the state threshold. Federal payroll deposits may also trigger the next-day rule if accumulated employment taxes reach $100,000 on any day during a deposit period. Maryland requires zero returns in some cases even when no tax is due, and monthly or quarterly sales and withholding filing frequency must match the account setup on Maryland Tax Connect.
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Key IRS Deadlines in May 2026 Explained 🏛️
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May 1, 6, 8, 13, 15, 20, 22, 28, and 29 — Semiweekly federal payroll deposits
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Who this generally affects:
- Employers on the semiweekly deposit schedule.
- Businesses that run regular payroll and deposit withheld federal income tax plus employer and employee Social Security and Medicare taxes through EFTPS.
What is due:
These are recurring deposit dates for payroll taxes based on when wages were paid. The IRS second-quarter tax calendar breaks them out across the month. For example:
- May 1 covers certain payrolls paid April 25–28.
- May 6 covers certain payrolls paid April 29–May 1.
- May 8 covers certain payrolls paid May 2–5.
- Additional May deposit dates continue throughout the month under the same Wednesday/Friday pattern.
If your payroll schedule puts you on the semiweekly system, May is not about one big deadline. It is about a series of smaller deadlines that repeat all month long.
How to handle it:
- 1. Confirm whether your business is a monthly or semiweekly depositor.
- 2. Make sure your payroll provider or internal team is scheduling deposits through EFTPS, not just running payroll.
- 3. Double-check unusual payroll runs, bonuses, or off-cycle checks, since those can affect the deposit timing.
May 11, 2026 — April tip reporting and Form 941 for Q1
Because May 10 falls on a Sunday in 2026, this deadline lands on Monday, May 11.
Who this affects:
- Employees who received $20 or more in tips during April.
- Employers required to file Form 941, Employer’s Quarterly Federal Tax Return, for the first quarter of 2026.
What is due:
- Tipped employees must report April tips to their employer.
- Employers that deposited all first-quarter payroll taxes in full and on time generally must file Form 941 by May 11.
Why it matters:
Tip reporting affects wage reporting, withholding, and year-end tax forms. Form 941 is one of the IRS’s core payroll reports, and late filing can create avoidable notices and penalties.
How to handle it:
- Employees should report tips using the employer’s approved process or the equivalent of Form 4070 information.
- Employers should reconcile payroll records, taxable wages, withholding, and deposits before filing Form 941.
- If numbers do not match, it is better to pause and correct the records than to rush through a filing that will trigger questions later.
May 15, 2026 — Monthly federal payroll deposit for April wages
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Who this affects:
- Employers on the monthly deposit schedule.
What is due:
- Federal income tax withheld from wages.
- Employee and employer shares of Social Security and Medicare taxes for wages paid in April 2026.
How to pay:
- Through EFTPS or an authorized payroll service acting on the employer’s behalf.
May 15, 2026 — Certain tax-exempt organization filings
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Who this may affect:
- Calendar-year nonprofits and tax-exempt organizations.
What may be due:
- Annual information returns such as Form 990, 990-EZ, 990-PF, or 990-N, depending on the organization.
- Extension request Form 8868, if more time is needed to file.
Key Maryland deadlines in May 2026 Explained 🏦
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May 15, 2026 — Maryland employer withholding return and payment for April
Who this generally affects:
- Maryland employers on a monthly withholding filing schedule.
What is due:
- The Maryland withholding return and payment for tax withheld from employee wages in April 2026.
How to file and pay:
- Most employers use Maryland Tax Connect to file returns, make direct-debit payments, and submit zero returns when needed.
⚠️Maryland requires a filing even when no tax is due in some cases. If payroll was paused or wages were low, do not assume you can simply skip the filing.
If you are unsure of your filing frequency:
Check your prior Maryland filings or notices from the Comptroller. Monthly, quarterly, annual, and accelerated filing rules do not all work the same way.
Ongoing Maryland accelerated withholding deadlines
Who this affects:
- Employers that withheld $15,000 or more during the preceding calendar year and accumulate $700 or more in withholding during a pay period.
What is required:
- Filing and payment generally within three business days after the payroll date.
For businesses with larger or variable payroll, this rule can create much faster turnaround than the standard monthly schedule. If you have crossed into accelerated filing territory, your internal payroll process needs to reflect that.
May 20, 2026 — Maryland sales and use tax return and payment for April
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Who this affects:
- Businesses required to collect and remit Maryland sales and use tax.
What is due:
- The return and payment for the reporting period ending in April 2026 for monthly filers.
Why it matters:
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Sales tax is money you collected from customers on the state’s behalf. It is not your operating cash, even if it is sitting in your bank account. That is why missed sales tax deadlines can escalate quickly.
How to handle it:
- 1. Reconcile taxable sales before filing.
- 2. Make sure exempt sales are documented properly.
- 3. Keep sales tax funds separate in your cash-flow planning so the May 20 payment does not become a surprise.
How to decide which deadlines apply to you
A simple way to sort through May is to group deadlines by role.
If you are an individual taxpayer
You may not have a standard May income tax filing deadline. But May still matters if you:
- • Own a sole proprietorship or side business.
- • Employ household help or business employees.
- • Receive tips or supervise tipped workers.
- • Need to prepare for the June 15 estimated-tax deadline coming next month.
If you own a small business
Focus on:
- • Federal payroll deposits.
- • Maryland withholding obligations.
- • Maryland sales tax filings.
- • Q1 payroll reporting follow-up, especially Form 941.
If you run payroll as an employer
Make sure you know:
- • Whether you are a monthly or semiweekly federal depositor.
- • Your Maryland filing frequency.
- • Whether accelerated Maryland withholding rules apply.
- • Who is responsible for deposits and returns—your team, your payroll company, or both.
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How AllTax Accounting Can Help
If you are not completely sure which May 2026 deadlines apply to your business or household, AllTax can help you sort them out quickly. We can review your payroll schedule, Maryland filing frequency, and monthly compliance calendar so you are not left guessing—or paying penalties for avoidable misses.
If May deadlines have started to feel repetitive or easy to overlook, this is a good time to build a cleaner system. Reach out to AllTax, and we will help turn your recurring tax obligations into a process that feels more organized and far less stressful.
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Practical steps to stay ahead in May