#tax-deadlines
Tax Deadlines
Important tax filing deadlines and compliance dates to remember
Quarterly Estimated Taxes for the Self-Employed in 2026: Safe Harbors, Form 1040-ES, and the Annualized Income Method
A working guide to the 2026 quarterly estimated tax rules for freelancers and self-employed earners — the two IRS safe harbors (90% current year, 100%/110% prior year), the four uneven due dates, Form 1040-ES, the annualized income method for lumpy earners, EFTPS vs Direct Pay, and the mistakes that trigger penalties at the 6–7% federal rate.
Schedules K-2 and K-3 in 2026: The Domestic Filing Exception, the 1-Month Deadline, and the Foreign Tax Credit Trap
Schedules K-2 and K-3 pulled even purely domestic partnerships and S-corps into international tax reporting starting in 2021. This guide explains the 2026 filing rules, the four-condition domestic filing exception, the January 15 partner notification and February 15 1-month K-3 request deadlines for calendar-year filers, the $250,000 small entity carve-out added in 2024, and the per-partner, per-month penalty math for non-compliance.
Form 2290 and the HVUT: How Trucking Operators File Heavy Highway Vehicle Use Tax Before the August 31 Deadline
Form 2290 funds federal highway maintenance through an annual excise tax on vehicles with a taxable gross weight of 55,000 pounds or more. Owner-operators and fleets owe up to $550 per truck and must file by August 31 — late filings trigger a 4.5% monthly penalty and DMV registration suspension.
Form W-2c and W-3c: How to Correct a W-2 Without Triggering Penalty Cliffs
Form W-2c fixes errors on previously filed W-2s, but the penalty structure stacks behind the original February 2 due date — $60, $130, $340, or $680 per form depending on how late you file. A practical guide to W-2c and W-3c filing, the 10-return e-file threshold, SSA mismatch letters, and reconciling with Form 941-X.
ACA Forms 1094-C and 1095-C: The 2026 Compliance Playbook for Applicable Large Employers
How Applicable Large Employers file Forms 1094-C and 1095-C for the 2025 reporting year. Covers the March 2 and March 31, 2026 deadlines, the post-2024 furnishing-on-request rule, the 2026 penalty amounts ($3,340 and $5,010 per employee), the new 90-day Letter 226-J response window, and the Line 14/16 coding errors that most often trigger IRS audits.
First-Time Penalty Abatement Goes Automatic in 2026: Clean-Compliance IRS Relief for Failure-to-File, Pay, and Deposit Penalties
Starting filing season 2026, the IRS will apply First-Time Penalty Abatement automatically for taxpayers with a clean three-year compliance record — wiping Failure-to-File, Failure-to-Pay, and Failure-to-Deposit penalties without a phone call or Form 843. Here is how the rollout works, who qualifies, and when reasonable cause is the smarter move.
PCORI Fee 2026: Self-Insured Plans, HRAs, and Form 720 by July 31
For plan years ending in 2025, self-insured plan sponsors and HRA employers must file Form 720 by July 31, 2026 and pay $3.84 per covered life ($3.47 for plan years ending before October 1, 2025). This guide covers who owes the fee, the three approved methods to calculate average covered lives, why HRAs count employees only, and the common Form 720 filing mistakes that trigger IRS notices.
Form 706 Portability and the DSUE: How Surviving Spouses Inherit Up to $30 Million of Federal Estate Tax Exemption
Filing IRS Form 706 to elect portability lets a surviving spouse inherit up to $15 million of unused federal estate tax exemption (the DSUE), shielding combined estates of up to $30 million from the 40% federal estate tax in 2026. Miss the nine-month deadline and Rev. Proc. 2022-32 still allows a late election within five years of death.
Form 990, 990-EZ, and 990-N: How Nonprofits Choose the Right Annual Return and Avoid Automatic Revocation
Nonprofits with gross receipts of $50,000 or less file Form 990-N; those under $200,000 receipts and $500,000 assets file 990-EZ; everyone else files the full 990. This guide covers thresholds, deadlines, late penalties up to $120 per day, and the three-year automatic revocation rule that quietly strips exempt status.
Form 5500-EZ Solo 401(k) Filing Threshold: When Self-Employed Plans Cross the $250,000 Asset Trigger
A Solo 401(k) crosses into mandatory Form 5500-EZ filing once combined plan assets exceed $250,000 on the last day of the plan year. Late filings cost $250 per day up to $150,000 annually, but Rev. Proc. 2015-32 caps catch-up filings at $1,500 per plan if no penalty notice has been issued.
Small Business Taxes 2026: A Complete Obligations Guide for New Business Owners
A 2026 walkthrough of every small business tax obligation—federal income, self-employment, payroll, sales, and excise—with the full filing calendar, quarterly estimated tax safe harbors, OBBBA-era changes (permanent QBI, $1.21M Section 179, restored 100% bonus depreciation), and the recordkeeping habits that prevent penalties.
The Stress-Free Tax Season Workflow: How to Catch Up, Organize, and File With Confidence
A six-week framework for small business owners to catch up unreconciled books, assemble a standardized year-end financial package, and hand off cleanly to an accountant—anchored by the 2026 federal filing deadlines.