Tax Deadline Calendar Skill

Track federal and state tax filing deadlines, estimated tax payment windows, payroll deposit schedules,
and information return due dates. This skill helps Sam Ledger proactively manage compliance calendars,
generate reminders, and calculate penalty exposure for late filings.

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When to Use This Skill

Trigger phrases:

• - "What taxes are due this month?"
• "When is [entity type]'s tax return due?"
• "Set up a tax deadline calendar for [client]"
• "When do I need to pay estimated taxes?"
• "What's the penalty for filing [form] late?"
• "Did we miss any tax deadlines?"
• "Extension deadline for [form]?"
• "Payroll tax deposit schedule for [company]"
• "1099 deadline this year?"
• "W-2 due date?"

NOT for:

• - Preparing or filing tax returns — requires licensed CPA / PTIN
• Calculating actual tax liability (income, payroll, sales tax owed)
• Multi-state nexus analysis or sales tax registration advice
• State-specific filing requirements beyond major deadlines (consult state CPA)
• International tax deadlines (FBAR, Form 5471, etc.) — specialized skill needed
• Prior-year amended return deadlines beyond standard 3-year lookback guidance

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Federal Tax Deadline Reference

Business Entity Filing Deadlines

Entity Type	Form	Standard Deadline	Extended Deadline
S-Corporation	1120-S	March 15	September 15
Partnership

1065 | March 15 | September 15 | | C-Corporation (Dec. 31 FYE) | 1120 | April 15 | October 15 | | C-Corporation (other FYE) | 1120 | 15th day of 4th month after FYE | 6-month extension | | LLC (single-member, disregarded) | Schedule C / 1040 | April 15 | October 15 | | LLC (multi-member, partnership) | 1065 | March 15 | September 15 | | Non-profit | 990 / 990-EZ | 15th day of 5th month after FYE | 6-month extension | | Sole Proprietor | Schedule C / 1040 | April 15 | October 15 | | Trust / Estate | 1041 | April 15 | September 30 |

Key rule: S-Corps and Partnerships file March 15 so that K-1s reach shareholders/partners before
the individual April 15 deadline. Missing March 15 cascades to missed individual returns.

Individual Filing Deadlines

Form	Standard Deadline	Extended Deadline	Notes
Individual (1040)	April 15	October 15	Extension via Form 4868
FBAR (FinCEN 114)

April 15 | October 15 | Auto-extended; no separate filing needed | | FATCA (Form 8938) | April 15 (with 1040) | October 15 (with extension) | | | Gift Tax (709) | April 15 | October 15 (with 1040 extension) | |

Estimated Tax Payment Schedule (Federal)

Applies to: individuals with self-employment income, pass-through owners, sole proprietors.

Payment	Tax Year	Due Date
Q1	January 1 – March 31	April 15
Q2

April 1 – May 31 | June 15 |
| Q3 | June 1 – August 31 | September 15 |
| Q4 | September 1 – December 31 | January 15 (following year) |

If April 15 or other dates fall on a weekend or holiday, the deadline shifts to the next business day.

Safe harbor thresholds (avoid underpayment penalty):
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Underpayment penalty rate: Federal funds rate + 3% (IRS adjusts quarterly). Currently ~7-8% annualized.

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Payroll Tax Deadlines

Federal Payroll Deposits

Deposit schedule depends on lookback period (July 1 – June 30 of prior year):

Lookback Period Tax Liability	Deposit Schedule	Deposit Deadline
≤ $50,000	Monthly depositor	15th of following month
> $50,000

Semi-weekly depositor | Wed–Fri payroll → following Wednesday; Mon–Tue payroll → following Friday |
| < $2,500/quarter | Quarterly depositor | With Form 941 filing |
| $100,000+ in single day | Next-day depositor | Next banking day — no exceptions |

Key payroll tax forms and deadlines:

Form	What	Deadline
Form 941	Quarterly payroll tax return	Last day of month following quarter end (Apr 30, Jul 31, Oct 31, Jan 31)
Form 940

Annual FUTA return | January 31 (or Feb 10 if all deposits made on time) |
| Form W-2 | Wage statements to employees | January 31 |
| Form W-3 | Transmittal to SSA | January 31 |
| Form W-2 corrections (W-2c) | Corrected wages | ASAP; penalties increase with delay |

Form 941 Quarterly Calendar (2026)

Quarter	Period	Filing Deadline	Deposit Deadline (monthly)
Q1	Jan–Mar	April 30, 2026	15th of each following month
Q2

Apr–Jun | July 31, 2026 | 15th of each following month | | Q3 | Jul–Sep | October 31, 2026 | 15th of each following month | | Q4 | Oct–Dec | January 31, 2027 | 15th of each following month |

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Information Return Deadlines

1099 Series

Form	Purpose	Recipient Copy	IRS Paper	IRS E-File
1099-NEC	Non-employee compensation ≥ $600	January 31	January 31	January 31
1099-MISC

Rents, royalties, other income ≥ $600 | January 31 | February 28 | March 31 | | 1099-INT | Interest ≥ $10 | January 31 | February 28 | March 31 | | 1099-DIV | Dividends ≥ $10 | January 31 | February 28 | March 31 | | 1099-R | Retirement distributions | January 31 | February 28 | March 31 | | 1099-K | Payment card transactions ≥ $5,000 (2024 threshold) | January 31 | February 28 | March 31 | | 1099-B | Brokerage proceeds | February 15 | February 28 | March 31 |

E-file mandate: Filers with 10+ information returns (combined all types) MUST e-file starting 2024.
The 10-return threshold replaced the prior 250-return threshold.

W-2 Deadlines

• - January 31: Send to employees AND file Copy A with SSA (paper AND e-file — same deadline)
• No extension available for W-2 filing with SSA without Form 8809

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Extension Filing Reference

Form	What	How to File	Extends To
Form 4868	Individual 1040 extension	File by April 15	October 15
Form 7004

Business return extension (1120, 1065, 1120-S) | File by original deadline | +6 months | | Form 8868 | Non-profit 990 extension | File by original deadline | +6 months | | Form 8809 | Information return extension (W-2, 1099) | File by original deadline | +30 days (hardship only) |

Critical: Extensions extend the TIME TO FILE, not the time to pay.
Tax owed must still be estimated and paid by the original deadline or interest + penalties accrue.

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Penalty Exposure Calculator

Failure to File (FTF)

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Failure to Pay (FTP)

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Combined FTF + FTP (when both apply)

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Information Return Penalties (1099/W-2)

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Small business definition: Average annual gross receipts ≤ $5M for 3 prior tax years.

Payroll Tax Failure to Deposit (FTD)

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2026 Key Dates Calendar

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Compliance Checklist Generator

When a user asks for a client compliance calendar, generate a checklist:

Inputs required:
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Output: Client Compliance Checklist

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State Tax Deadline Overview

Most states conform to federal deadlines, but key exceptions:

State	Notable Difference
California	FTB: C-Corp April 15; S-Corp March 15; Individual April 15 (or next business day)
New York

Conforms to federal dates; NYC adds separate NYC-4S/NYC-4 for C-Corps |
| Texas | No state income tax; franchise tax (TX No Tax Due/05-163) due May 15 |
| Florida | C-Corp F-1120 due: April 1 (or 4.5 months after FYE) |
| Illinois | Conforms to federal with IL-specific extensions |
| Pennsylvania | Conforms to federal for individuals; RCT-101 for C-Corps April 15 |

Always verify: State deadlines change. Use this as a starting framework, not the definitive source.
Confirm with state revenue department or state-licensed CPA.

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Reminder Setup (OpenClaw Cron)

To set up automated deadline reminders via cron:

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Sample cron payload (S-Corp March 15 deadline):

{
  "schedule": { "kind": "at", "at": "2026-03-01T09:00:00-06:00" },
  "payload": {
    "kind": "systemEvent",
    "text": "TAX REMINDER: S-Corp/Partnership returns (Form 1120-S / 1065) due March 15 — 14 days away. Confirm K-1s being prepared, extension decisions made, and balance due estimated."
  }
}

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Penalty Abatement Notes

First-time penalty abatement (FTA):

• - Available for FTF, FTP, and FTD penalties
• Requires: clean compliance history (no penalties in prior 3 years) + all returns filed
• Request via Form 843 or by calling the IRS
• IRS grants FTA liberally — always ask before paying FTF/FTP penalties

Reasonable cause abatement:

• - Available when failure was due to circumstances beyond taxpayer's control
• Document: what happened, why it prevented compliance, steps taken to comply ASAP
• Examples: natural disaster, serious illness, reliance on erroneous IRS advice

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Integration Points

• - qbo-automation — Pull payroll and vendor payment data to identify 1099 filing obligations
• crypto-tax-agent — Crypto tax events feed into individual 1040 and Schedule D deadlines
• kpi-alert-system — Trigger compliance calendar reminders via cron/alert system
• compliance-monitor — Broader compliance tracking beyond tax deadlines
• startup-financial-model — Estimated tax payments flow from projected taxable income model

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Quick Reference: Most Common Deadline Misses

1. 1. 1099-NEC January 31 — Most commonly missed information return (same day recipient AND IRS)
2. S-Corp March 15 — Founders forget pass-through entities file earlier than individuals
3. Estimated Q1 taxes April 15 — Individual owners skip this and face underpayment penalty
4. Form 940 January 31 — FUTA often forgotten since it's only annual
5. Extension ≠ payment extension — Filing an extension without paying causes FTP penalties to accrue