Some states make sales tax filing straightforward — and then there are the ones that keep even seasoned pros on their toes.

In this episode of Beyond Death & Taxes, Matt and Clay dig into one of Avalara’s most downloaded webinars: the 10 trickiest states for sales tax returns. From inconsistent deadlines to confusing location reporting and “alphabet soup” schedules, they walk through the quirks and complexities that make filing in certain states uniquely challenging.

You’ll hear expert insights from Avalara’s tax pros as they break down what makes states like California, Colorado, Illinois, New York, Louisiana, Texas, and more so difficult — and what finance teams should be watching out for as rules, thresholds, and interpretations continue to shift.

And before diving in, the hosts pay their respects in the Compliance Graveyard to one of the most persistent myths in the industry: the idea that all states handle sales tax the same way. (Spoiler: they do not.)

Key Takeaways

• States vary widely: Sales tax rules, deadlines, and formats differ dramatically from state to state.
• Nexus keeps evolving: Physical, economic, and marketplace nexus rules continue to shift — and vary by jurisdiction.
• Some states are especially tough: Places like California, Colorado, Illinois, New York, and Louisiana come with added complexity.
• Accurate data matters: Clean, consistent tax data is essential for timely and accurate returns.
• Deadlines can get messy: Filing frequencies and prepayment requirements change as you hit new thresholds.

Whether you file in two states or twenty, this episode will help you better understand the pitfalls, patterns, and prep work needed to stay compliant across the country.