The Law Offices of O'Connor & Lyon

07/17/2025

The One Big Beautiful Bill Act’s 90% cap on federal gambling loss deductions is an awful change. Keeping detailed records and using the session method will be more impactful than ever! Read more:
https://www.oconnorlyon.com/blog/2025/7/17/the-one-big-beautiful-bill-act-gambling-taxes-and-the-session-method

The OBBBA and Gambling Taxes: A New Curveball for Connecticut Bettors In 2025, the tax consequences of gambling got quite the shake-up with the passage of the One Big Beautiful Bill Act (OBBBA). Tucked into its 900 plus pages is a provision that’s got gamblers reaching for their calculators and ma

08/01/2023

Gambling can have some really unfortunate tax consequences, consequences that are especially unfair for people living in Connecticut. Inform yourself on your reporting options if you have any gambling income, especially if you gamble on slot machines (online or at the casino).

Gambling in Connecticut and Taxes In May of 2021 Connecticut legalized online casino gaming and sports wagering (you can find the history and text of the bill here: https://www.cga.ct.gov/asp/cgabillstatus/cgabillstatus.asp?selBillType=Bill&which_year=2021&bill_num=6451 ) This was

08/24/2022

The IRS just announced automatic relief from failure-to-file penalties for most 2019 and 2020 tax returns, but unfiled returns must be sent in before September 30th to qualify. Read more here:

Today, the IRS issued  Notice 2022-36 .  The notice announces the IRS’s intention to automatically waive failure-to-file penalties for many return types, provided the returns are filed on or before September 30th. What Types of Returns are Covered? The automatic reli

06/22/2022

US Supreme Court set to review Circuit Court split on applicability of non-willful FBAR penalties.

As we’ve covered previously in our blog , we’ve been closely following a schism that has developed in different Circuit Courts in the US regarding the IRS’s assertion that 31 U.S.C. §5321(a)(5)(A) provides it with the authority to assert a $10,000 civil penalty (adjusted for inflation) for e

12/09/2021

As part of its recent amnesty program push, the CT DRS is sending out notices threatening Use Tax audits based on information turned over by U.S. Customs if targeted taxpayers don't come forward voluntarily.

I was recently informed by a prospective client that she received a notice from the CT DRS advising her that she had been “identified as a potential audit candidate” from information “U.S. Customs has provided the Department of Revenue Services.” The notice goes on to advise the recipient of...

12/03/2021

How is the Build Back Better Act Going to Impact Your Taxes?https://www.oconnorlyon.com/blog/2021/12/3/will-the-upcoming-build-back-better-tax-law-changes-impact-you

11/01/2021

The CT DRS Tax Amnesty program is now live and accepting applications! The program offers a complete waiver of penalties and a 75% reduction to applicable interest. Read more about the program at the following link:

Late last week, the CT DRS published a press release on their website , formally announcing the state’s long-awaited tax amnesty program. The CT DRS has launched a new website specifically related to the amnesty program, GetRightCT.com . Who can take advantage of the 2021 CT DRS Tax Amnesty Pro

08/02/2021

New Taxes, Higher Tax Rates, and Expanded Tax Regimes for High Income Individuals in the Most Recent Biden Administration Tax Proposal. www.oconnorlyon.com/blog/2021/8/2/biden-administrations-plan-to-strengthen-taxation-of-high-income-taxpayers

We previously discussed the Biden administration’s plan to give the IRS access to bank account and credit card transaction data here: https://www.oconnorlyon.com/blog/2021/6/24/government-proposal-to-give-individual-and-business-bank-account-and-credit-card-transaction-data-to-the-irs-annually but

07/12/2021

The Connecticut DRS has announced a tax amnesty program with broad eligibility among taxpayers and tax types -- the first such program to be offered in years. The application window opens in November and only runs for 3 months. If you have unfiled returns or owe back taxes to the state of Connecticut, start making preparations now so you can take advantage of the limited amnesty window.

On June 23, 2021, Governor Ned Lamont signed SB 1202 , implementing the state budget for the FY 2022-2023 biennium.  Section 486 of the act directs the Commissioner of Revenue Services to establish a tax amnesty program applicable to taxable periods ending on or before December 30, 2020.

06/28/2021

We've recently posted an article on our blog that covers the basics of resolving delinquent tax liabilities with the Connecticut DRS. Check it out:

In most instances, people who owe the IRS back taxes also owe delinquent state taxes.  Given the disparate tax rates applicable to income at the federal and state level, federal income tax liabilities often greatly exceed those at the state level, leading many taxpayers and practitioners to

06/24/2021

A proposal from the Biden administration would force banks/investment companies/credit card processors to turn over your data to the IRS annually. Read more about this proposal here: www.oconnorlyon.com/blog/2021/6/24/government-proposal-to-give-individual-and-business-bank-account-and-credit-card-transaction-data-to-the-irs-annually

IRS May Get Copies of your Bank Account Information and Your Credit Card Transactions From Banks and Payment Processors In May 2021 the Department of the Treasury published “General Explanations of the Administration’s Fiscal Year 2022 Revenue Proposals”. These proposals are contained in “Th...

04/16/2021

The eighth installment of my 'A Practical Guide to Your Tax Return' series covers capital gains. Long term, short term, limitations, exceptions - this is a great starting point to begin to understand the taxation of capital gains.
Could trading a house for a Lamborghini create capital gains? (I'm not trying to clickbait you, the answer is yes, yes it can)

Capital Gains Overview and Some Definitions Sell stuff for more than it cost you? Capital gains. As you can imagine this is an incredibly broad topic that will impact everyone eventually, whether you sell a house, a beanie baby, or that pokemon card you’ve been holding onto since your childhood L