Our Blog
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The USPS postmark change you need to know about before you mail anything tax-related
- May 13, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
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A USPS rule change means that the postmark on your tax-related mail may no longer reflect the day you actually dropped it off, and the IRS still uses that postmark to determine whether you filed on time. For taxpayers in rural areas especially, this gap could be the difference between a timely filing and a costly late penalty. Read on to understand exactly what changed, why it matters, and the simple steps you can take to protect yourself.
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Which retirement plan is best for a self-employed owner: SEP, SIMPLE, or Solo 401(k)?
- May 6, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
A practical guide to using a SEP IRA, SIMPLE IRA, or solo 401(k) strategically, covering contribution limits, deadlines, employee rules, tax planning, and when each plan makes the most sense.
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Filed an extension? How to use the time between now and October 15th
- April 29, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Filing a tax extension buys you time, but only if you use it wisely. From revisiting your April payment estimate to gathering missing documents and staying on top of current-year obligations, the months between now and October 15th are a valuable planning window. Read on to learn how to make the most of your extension and avoid a costly repeat of the same tax challenges next year.
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When unequal cash creates unequal risk: disproportionate distributions in S-corps
- April 15, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Disproportionate distributions in S corporations can trigger unintended tax consequences and even loss of S status. Learn where the risks arise and how strategic planning can preserve compliance while achieving unequal economic outcomes.
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Living trust myths vs. reality: what a revocable trust really does
- April 7, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Revocable living trusts are widely used and widely misunderstood. This article explains what revocable trusts actually do, what they don’t do, and why proper design, funding, and coordination matter. Understanding these nuances can help prevent surprises and improve estate planning outcomes.
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A smarter way to manage your taxes: inside the IRS online account
- April 2, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
The IRS Individual Online Account gives taxpayers secure, year-round access to tax records, balances, payments, and official notices all in one place. Read on to discover how this powerful tool works and how it can make staying on top of your taxes easier than ever.
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Why estate taxes aren’t the only inheritance-related costs to consider
- March 18, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
Estate planning discussions often focus on the federal estate tax exemption, but most families face different challenges when transferring wealth. Probate fees, state-level taxes, capital gains exposure, and administrative complexity can all erode inheritances – even for estates well below the federal threshold. A comprehensive estate plan addresses these hidden costs, not just headline tax numbers.
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S-corporations 101: FAQs for business owners
- March 4, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
S-corporations are one of the most frequently discussed (but often misunderstood) tax structures for small business owners. While they can offer real savings on self-employment taxes, the benefits aren’t automatic – they depend on your income level, involvement in the business, and whether you’re ready to manage the added compliance responsibilities. Here’s what you need to know about how S-corps work, who they’re right for, and what’s required to maintain one.
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Healthcare costs for the self-employed in 2026: strategies for rising premiums
- February 18, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
With the expiration of expanded ACA subsidies in 2026, self-employed professionals are facing significant premium increases with no employer to share the burden. While healthcare costs are rising, strategic planning can help reduce your total cost. The key is treating healthcare like any other business expense – strategically, proactively, and with tax efficiency in mind.
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The mega backdoor Roth: a straightforward strategy for high earners locked out of Roth IRAs
- February 4, 2026
- Posted by: Cummings, Keegan & Co
- Category: Article
For high-income professionals locked out of traditional Roth contributions, mega Roth conversions offer a powerful alternative. By contributing after-tax dollars to fill unused space under the $72,000 annual 401(k) limit and immediately converting them to Roth, eligible savers can funnel tens of thousands annually into tax-free growth.
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