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Loading Tax News…Ask Phil Video SeriesPublished on Mar 27, 2026
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 […]
Ask Phil Video SeriesPublished on Mar 20, 2026
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 […]
Ask Phil Video SeriesPublished on Mar 13, 2026
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 […]
Ask Phil Video SeriesPublished on Feb 21, 2026
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 […]
Ask Phil Video SeriesPublished on Feb 21, 2026
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 […]
Ask Phil Video SeriesPublished on Feb 8, 2026
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 […]
Ask Phil Video SeriesPublished on Jan 18, 2026
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 […]
Ask Phil Video SeriesPublished on Dec 26, 2025
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 […]
Ask Phil Video SeriesPublished on Dec 19, 2025
Today, Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, shares five essential tax tips every self-employed individual should know. Tip 1: Make Your Quarterly Estimated Payments As a self-employed taxpayer, you are responsible for paying your taxes quarterly. Missing these payments […]
Ask Phil Video SeriesPublished on Nov 28, 2025
Today, Optima Tax Relief’s Chief Tax Officer and Lead Tax Attorney, Phil, answers a common Reddit question: “Can I skip paying my taxes this year?” Technically, paying your taxes is a completely voluntary act. However, skipping your taxes is never a good idea. Penalty and Interest Risks The IRS can assess […]
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