Blog / Topic
Deadlines & Extensions
IRS tax deadlines, filing extensions, and what freelancers and small businesses should do before each due date.
- Books a Mess Before the October 15 Extension Deadline? No Clean P&L, and the Audit Risk Is YoursOctober 2026
If your books aren't reconciled by the October 15 extension deadline, you can't produce a clean profit and loss, you carry all the audit responsibility, and you may struggle to get a loan or mortgage. Here's how to fix it fast.
- 1099 and Haven't Filed Your 2025 Taxes? Here's Exactly What to DoSeptember 2026
Still a 1099 contractor with unfiled 2025 taxes? Here's what the failure-to-file penalty is actually costing you, and the exact steps to file now, even without every 1099 in hand.
- Filed a Tax Extension But Still Haven't Filed? What to Do Before October 15September 2026
Filed IRS Form 4868 back in April but still haven't filed your return? Here's what the October 15 extension deadline actually means, what penalties are already accruing, and the exact steps to catch up this week.
- IRS Website Down on Deadline Day? What Freelancers Should DoJune 2026
IRS system outages happen right before tax deadlines. Learn why, what to do if it happens to you, and how real-time bookkeeping keeps a freelancer's deadline from becoming a crisis.
- Q2 2026 Quarterly Taxes: What Freelancers Need to Do Before June 15June 2026
Q2 estimated taxes are due June 15, 2026. Learn what income to include, how to calculate your payment, and the exact steps to pay before the deadline.
- Q3 2026 Quarterly Taxes: How to Prepare for the September 15 DeadlineJune 2026
Q3 estimated taxes are due September 15, 2026 and cover income from June through August. Learn what to do now to avoid a surprise payment in the fall.
- Why Tax Deadlines Get Extended and What Freelancers Should DoMay 2026
Learn why IRS tax deadlines get extended, what it means for freelancers, and how to prepare so you don't scramble next time.