The second quarter estimated tax payment deadline is rapidly approaching. If you make quarterly payments, you have until June 16 to pay and avoid possible underpayment penalties. If you don’t currently make estimated payments, should you? In general, individuals should make payments if they expect to owe $1,000 or more ($500 for corporations) when they file their returns. This may include sole proprietors and other self-employed individuals, such as gig workers. Investors, partners in partnerships and S corp. shareholders also typically fall into this category. Contact us or use the IRS estimator to calculate how much you should pay in estimated taxes: https://bit.ly/3VjGqR1. © 2025