Quarterly Tax Payments: 5 Times You Shouldn’t Skip Them
Q3 is around the corner, and tax surprises are never fun. While most business owners know they need to make quarterly estimated payments, many people don’t realize there are other situations where estimates can save you from an unexpected tax bill — or worse, penalties.
Here are five common scenarios where quarterly tax estimates may be worth considering:
Your side hustle is picking up steam.
That extra income from consulting, freelancing, or selling online can add up fast. Since there’s usually no withholding, you could owe more than you think.
Your RSUs vested this year.
If restricted stock units vested in 2025, they may have been withheld at just 22%. For higher earners, that’s often well below your actual tax bracket — leaving you underpaid.
Your filing status changed.
Got married? Recently divorced? A change in status or dependents can shift your tax rate in a big way. Don’t wait until April to find out the difference.
You cashed in on investments or property.
Sold stock, real estate, or another big asset? Those gains can trigger significant taxes, and estimates can help soften the blow.
You started taking retirement income.
Social Security and retirement distributions aren’t always withheld correctly. If this is your first year collecting, it’s easy to fall behind without realizing it.
Why This Matters
Quarterly estimates aren’t just busywork – they’re a way to stay ahead, protect your cash flow, and avoid significant penalties and interest. If any of these scenarios sound familiar, now’s the perfect time to revisit your plan and make adjustments before Q3 ends.