Inheriting a $1.5 million 401(k) triggers a hidden double tax cliff for self-employed workers. Learn why your first tax return as a single filer could cost you the critical QBI deduction.
Filing a tax extension buys you time for paperwork, not time for payments. Learn how the 2026 dual-deadline paradox and new IRS AI tracking algorithms are trapping independent contractors and owner-operators.
Millions of independent contractors missed the April 15 dual deadline for 2025 returns and Q1 estimated payments. Here is how to file a retroactive extension to stop the 5% monthly IRS penalty.
Forty-two percent of independent contractors underpaid their estimated taxes in Q1 2026. A massive tax filing mistake is costing drivers thousands in missed deductions.
While mainstream media fixates on the end of the IRS Direct File program, independent contractors face a much bigger challenge. New OBBBA reporting rules and automated AI audits are reshaping the 2026 tax season for gig workers.
The Senate is voting on the future of IRS Direct File, but the tool is already offline for 2026. Gig workers and owner-operators must pivot to professional tax filing services to navigate new OBBBA tax deductions safely.
The 2026 tax season introduces massive new deductions for gig workers, including the $25,000 'No Tax on Tips' write-off. But with new AI-driven IRS audits targeting Venmo and PayPal accounts, independent contractors must file with precision to avoid triggering automated penalties.
Gig workers are skipping their 2026 tax returns due to IRS-ICE data sharing leaks. Here is why hiding triggers an automated AI audit and how to protect your income.
Late 2025 legislation has caused a massive bottleneck for 1099 workers this tax season. Discover why mixing up the 2025 and 2026 mileage rates on the April 15 dual deadline is triggering automated IRS penalties.