The Law Offices of O'Connor & Lyon

The Law Offices of O'Connor & Lyon The Law Offices of O'Connor & Lyon is a full service law firm, helping clients with resolution, tax

The One Big Beautiful Bill Act’s 90% cap on federal gambling loss deductions is an awful change. Keeping detailed record...
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

Gambling can have some really unfortunate tax consequences, consequences that are especially unfair for people living in...
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

The IRS just announced automatic relief from failure-to-file penalties for most 2019 and 2020 tax returns, but unfiled r...
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

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

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