Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, answers another tax question from Reddit: “I just received an IRS letter saying I owe $23,000 for 2019 and 2020 taxes I never filed. Has anyone successfully negotiated this down?” How You Can Owe Taxes Without Filing The IRS may have filed the returns […]
Ask Phil: Should I Wait 60 days to file my taxes?
Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, answers another question from Reddit about getting back into tax compliance. In this case, the taxpayer hasn’t filed taxes in 10 years and was told by an enrolled agent that they likely only need to file the last six years to become current with the IRS. However, they’re wondering if […]
Ask Phil: Phil’s 2026 Tax Season Predictions — Refunds, IRS Service, and the Tips Deduction
Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, shares his predictions and insights for the upcoming 2026 tax season. From refunds to IRS service levels, here’s what taxpayers can expect. Hot Take #1: Tax Refunds Will refunds go up or down this year? While some expect increases, Phil’s take is that refunds will likely stay about […]
Ask Phil: IRS Says No More Refund Checks???
Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, answers a common question: “Is the IRS really going to stop sending refund checks?” The short answer is partially yes. As of September 30, 2025, the IRS moved away from issuing paper refund checks, pushing taxpayers toward digital payments instead. Most Taxpayers Won’t Notice a Change About 94% […]
Ask Phil: IRS Direct File Is Gone — Here’s What You Can Use Instead
Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, addresses a growing concern: Is the IRS Direct File program going away in 2026? The answer is yes—IRS Direct File, which allowed certain taxpayers to file for free, has officially been discontinued and is not available for the 2026 tax season. What This Means for Taxpayers While this change may […]
Ask Phil: Is All My Debt Included When I File For Bankruptcy?
Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, answers another tax question from Reddit. This time, the topic is bankruptcy and how tax debt is treated during the process. The taxpayer in this scenario has a $25,000 tax debt with the IRS and is currently on an installment agreement. However, when reviewing […]