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Self-Employed Taxpayers Face New Compliance Challenges as IRS Automation Increases

Self-Employed Taxpayers Face New Compliance Challenges as IRS Automation Increases

by TIG Tax Services | Jan 16, 2026 | Tax Updates

The Internal Revenue Service has significantly expanded its use of artificial intelligence and automated systems to identify tax compliance issues among self-employed taxpayers. This technological shift represents a fundamental change in how the agency approaches tax...
Quarterly Tax Payments for Gig Workers: Do You Really Need Them? (Avoid Penalties in 3 Simple Steps)

Quarterly Tax Payments for Gig Workers: Do You Really Need Them? (Avoid Penalties in 3 Simple Steps)

by TIG Tax Services | Jan 16, 2026 | Tax Updates

If you're driving for Uber, delivering food, freelancing, or running any kind of gig work, you've probably wondered whether you need to make quarterly tax payments. The short answer? It depends on how much you expect to owe the IRS this year. Let's break...
1099-K Threshold Changes Are Creating Confusion for Gig Workers – Here's What TIG Clients Need to Know

1099-K Threshold Changes Are Creating Confusion for Gig Workers – Here's What TIG Clients Need to Know

by TIG Tax Services | Jan 15, 2026 | Tax Updates

Gig workers and freelancers across the country are facing unprecedented confusion as 1099-K reporting thresholds have undergone significant changes in recent years. The One Big Beautiful Bill Act, signed into law on July 4, 2025, fundamentally altered the landscape...
1099-K Confusion: Is It $600, $5,000, or $20,000? Here's What Gig Workers Need to Know Right Now

1099-K Confusion: Is It $600, $5,000, or $20,000? Here's What Gig Workers Need to Know Right Now

by TIG Tax Services | Jan 15, 2026 | Tax Updates

The 1099-K reporting threshold has changed multiple times over the past few years, creating significant confusion among gig workers and independent contractors. With 2026 now underway, taxpayers need clear guidance on what the current rules actually are and how they...
Understanding Quarterly Estimated Taxes for Freelancers

Understanding Quarterly Estimated Taxes for Freelancers

by TIG Tax Services | Jan 14, 2026 | Tax Updates

Freelancers and self-employed individuals face unique tax responsibilities that differ significantly from traditional employees. Unlike workers who have taxes automatically withheld from their paychecks, independent contractors must proactively manage their tax...
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Terry Investment Group Inc
T/A: TIG Tax Services
6700 Alexander Bell Drive
Suite 200
Columbia, Maryland 21046
Main: (667) 309-9555

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9613 Harfird Road
Suite C # 1274
Parkville, Maryland 21234-2150

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