Avalara Sidekick extension for Shopify tax insights

Sidekick, Shopify’s AI-powered commerce assistant, now has an Avalara extension — bringing real-time tax compliance insights directly into the merchant workflow.

• Tax compliance is one of the most common reasons merchants ask questions in Shopify; those questions often result in time-consuming investigation or support tickets.
• The new Avalara extension in Sidekick gives merchants the ability to get real-time answers to tax questions and understand the “why” behind outcomes.
• The extension means merchants no longer need to manually investigate across platforms or reach out to support staff with questions.

By allowing merchants to ask questions, surface insights, and receive contextual guidance directly within Shopify, Sidekick simplifies how users interact with the tools and systems behind their operations — helping businesses run and grow more efficiently.

As Shopify introduces Sidekick app extensions, Avalara is proud to be included in this next phase of partner innovation — giving merchants the ability to access tax compliance insights in real time right in their workflow. For complex operational areas like tax, Sidekick represents a key shift: Instead of being forced to work across multiple systems, merchants can simply ask questions and get answers in context.

Tax compliance is one of the most complex and high-risk aspects of running a business. It’s also one of the most common sources of merchant questions — often requiring time-consuming investigation or support tickets to resolve.

Shopify included Avalara in the launch of Sidekick app extensions to help address that challenge directly.

Avalara combines deep tax expertise and agentic tax and compliance with platform-level visibility into how taxes are calculated, configured, and applied — making complex tax workflows more observable, explainable, and actionable. More than simply providing answers, this extension will help merchants understand the “why” behind outcomes.

With the Avalara extension in Sidekick, merchants can get immediate clarity on the tax questions they face every day, such as:

• Is Avalara connected and active?
• Why does this order have zero tax calculated on it?
• What states do I have nexus in?
• Does this customer have a valid certificate on file?
• Are any of my products missing a tax code?

Instead of manually investigating across platforms or reaching out to support staff, merchants can now ask these questions directly within Sidekick — and get answers in real time.

The Avalara extension is designed around the real issues merchants encounter, helping surface and explain how their tax setup behaves. Key capabilities include:

Connection and settings
Know whether Avalara AvaTax is connected and active, which environment is in use, and whether key settings are configured correctly — including commit timing, shipping tax settings, and product synchronization.

Order tax details
Get detailed visibility into how tax was calculated on a specific order, including jurisdiction-level breakdowns, line-item details, and explanations for unexpected or zero-tax outcomes.

Nexus configuration
Confirm where the business is currently configured to collect tax, including nexus settings across states, countries, VAT/GST registrations, and cross-border scenarios.

Customer exemptions and certificates
Verify whether a customer is tax-exempt, whether a valid exemption certificate is on file, and why an exemption may not have applied to an order.

Product tax codes
Understand how products are classified for tax purposes, identify missing tax codes, and confirm whether products are properly synced with AvaTax.

Together, these capabilities transform Sidekick into a self-service layer for tax troubleshooting — reducing reliance on support and accelerating time to resolution.

Context is what makes the Avalara Sidekick extension experience different.

The extension is built to answer the same questions merchants already ask support teams — using live configuration data and transaction details — all within the Shopify environment. That means less time searching for answers and more time acting on them.

Designed to show what’s happening behind the scenes, it helps merchants resolve issues faster while giving teams greater visibility into how their tax configuration operates across Shopify and Avalara.

This launch represents an important step toward more intelligent, integrated commerce experiences.

Sidekick app extensions have begun rolling out to merchants. To begin exploring, install the Avalara extension and paste one of these sample prompts into Sidekick:

1. Is Avalara connected and active?
2. Why does this order have zero tax calculated on it?
3. What states do I have nexus in?
4. Does this customer have a valid certificate on file?
5. Are any of my products missing a tax code?

Want to learn more about Avalara for Shopify? Connect with our team.

What is the Avalara extension in Sidekick?

The Avalara extension in Sidekick gives merchants access to real-time tax compliance insights directly in their Shopify workflow, versus having to navigate between platforms or open a support ticket to get answers to tax questions.

What are the benefits?

The Avalara extension in Sidekick helps merchants with real issues in real time, answering questions and providing understanding around the “why” of outcomes. Whether it’s questions about Avalara connectivity, settings for nexus, exempt sales, or others, it provides a new self-service layer for troubleshooting tax issues.

Why do merchants need tax support?

Tax compliance is complex, with rules that vary by jurisdiction and regulations that can change quickly. It generates a lot of merchant questions, and resolution often requires support tickets or time-consuming investigation. The Avalara Sidekick extension can reduce the time spent searching for answers, so merchants can act more quickly.