#tax-deadlines
Important tax filing deadlines and compliance dates to remember
Self-employed workers and freelancers who skip quarterly estimated tax payments face IRS underpayment penalties even when they file on time — here's how the pay-as-you-go system works, how to calculate what you owe each quarter, and how the safe harbor rule protects you from guessing wrong.
A practical guide to Form 1040-ES—who must file, how to calculate quarterly estimated payments, 2026 due dates, the safe harbor rule, and how to avoid IRS underpayment penalties as a freelancer or small business owner.
Step-by-step guide to Form 1099-NEC — who must file, the $600 threshold (rising to $2,000 in 2026), the January 31 deadline, the penalty schedule ($60–$340 per form), and how to avoid the most common contractor reporting mistakes.
For tax year 2026 calendar S-corps, Form 1120-S is due March 15, 2027 (Form 7004 extends to September 15, 2027); late §6699 is $260/shareholder/month.
Understand the critical deadlines for electing S-corp tax status and learn how to manage your records efficiently in Beancount. This guide provides essential insights for small business owners to navigate tax-saving opportunities.
A comprehensive month-by-month guide to the 2025 federal tax deadlines for U.S. small-business owners, helping you avoid penalties, manage cash flow, and stay audit-ready.
