Waiting until year-end to evaluate what you owe can lead to underpayment penalties or unexpected balances. By checking in now, you can adjust payments based on your actual financial performance so far this year. Even if you’ve been consistent with payments, changes in income or tax law may impact what you owe. A midyear review provides clarity—and gives you time to make informed decisions before deadlines approach.

—especially when working across state lines. Even if your business is not physically located in another state, you may still have obligations depending on where your customers are. Staying organized with your records and understanding where your responsibilities lie is key to avoiding surprises later. Midyear is a great time to review your activity and ensure your reporting processes are aligned. If you haven’t looked at this recently, now is the time.

One of the most common issues we see is missing documentation—specifically W-9s and Certificates of Insurance (COIs). Before continuing to work with any vendor, make sure you have: • A completed W-9 on file • Proof of insurance, if applicable If you’ve paid vendors this year without proper documentation, it’s not too late to correct it—but waiting will only make things more complicated as year-end approaches. Strong vendor processes now mean a smoother 1099 season later. If y

Employers may face $50 fines per W-2 not filed, back withholding for Social Security and Medicare taxes, and 100% of the employer’s share of those taxes. If the IRS believes the misclassification was intentional, penalties could escalate to criminal charges, with fines as high as $500,000. On top of that, your workers’ compensation carrier may audit you for unpaid premiums. Bottom line: worker classification matters. When in doubt, apply the Duck Test, check the ABC Test, and