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: 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: 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 […]
Ask Phil: Ready for the 2026 Tax Season?
Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, breaks down what you need to know to get ready for the 2026 tax season. The IRS has already started its “Get Ready” reminders, and being proactive now can help you avoid penalties, interest, and unnecessary stress. Gather and Organize Your Documents Start early by […]
Ask Phil: What is a CSED?
Today, Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, answers a Reddit question about CSEDs: “If my CSED is 11/15/25, does it expire at the beginning or end of the month?” To get there, he breaks down what a Collection Statute Expiration Date (CSED) actually is and how the IRS calculates it. What the CSED Really Is […]