Avalara’s Avi integrates AI into Outlook to redefine tax compliance workflows

Avalara has introduced Avi, an AI assistant embedded into Microsoft Outlook, signalling a shift towards proactive, agentic compliance that embeds automation directly at the initial point of document entry, enhancing accuracy and reducing manual effort.

Tax compliance workflows continue to evolve swiftly under the dual forces of rising regulatory complexity and accelerating digital transformation. In a notable advancement, Avalara has integrated its AI assistant, Avi, directly into Microsoft Outlook, positioning compliance actions right at the frontline where business documents first arrive. This integration, slated for general availability in January 2026, exemplifies Avalara’s ambitious vision for what it terms “agentic compliance”, AI agents autonomously executing and coordinating compliance tasks while preserving essential human oversight.
Traditionally, invoices and vendor documents entering organisations arrive as email attachments, which then undergo a manual, often fragmented process of review, data entry into ERP systems, validation, and storage. Avalara’s Avi fundamentally reimagines this flow by embedding automation directly into Outlook. Upon receipt of an invoice, Avi digitises the document, extracts critical data, applies relevant tax rules considering geography, product types, and exemption statuses, validates compliance with e-invoicing mandates, and prepares the data for approval and ERP integration. This shifts the inbox from a passive repository to an active compliance checkpoint, enabling finance, procurement, and tax teams to identify and address risks earlier in the transaction lifecycle.
What sets Avi apart is its agentic execution model rather than simple rule-based automation. Avi autonomously carries out multistep tasks, from data extraction to compliance validation, but crucially halts for human review before any payment or filing action. This blend of AI efficiency with human control is a cornerstone of Avalara’s approach to navigating complex and ever-changing tax landscapes. The integration also supports real-time compliance features such as continuous transaction controls (CTCs) and format validation, reducing audit risks by catching errors early.
This Outlook integration is part of a broader Avalara strategy to embed AI-driven compliance across familiar business tools and platforms. Beyond Outlook, Avi actively guides tax configuration inside NetSuite and interacts through browser extensions to assist with Avalara product setup and compliance task assignments. Moreover, Avi now interoperates with other enterprise AI agents via Google Gemini and A2A protocols, enabling seamless agent-to-agent collaboration, such as triggering registration updates from invoice validations, within Avalara’s highly reliable, cloud-spanning infrastructure.
Industry observers note that embedding compliance functionality upstream, at the point where documents first enter organisations and professionals already spend time, marks a significant shift from the long-standing model of post-entry compliance checks confined mostly to ERP systems. This not only accelerates review cycles and reduces manual data entry but also provides earlier visibility of potential tax issues, such as overcharges, empowering proactive vendor engagement and resolution.
Avalara’s rollout of Avi in Outlook aligns with the company’s broader Agentic Tax and Compliance™ initiative which leverages its Avalara LLM Framework for Agentic Applications (ALFA). This framework integrates enterprise large language models with dedicated AI servers and protocols to enable real-time, secure, and isolated compliance workflows across diverse platforms, blurring the lines between AI assistance and actionable compliance agents within everyday business environments.
For finance and compliance teams grappling with intensifying regulatory demands and the need for operational agility, Avalara’s new integration offers a promising tool to embed intelligent compliance into existing workflows seamlessly. By transforming the humble inbox into a compliance hub, Avi not only streamlines repetitive tasks but also elevates the accuracy and timeliness of compliance activities, auguring a future where AI and human oversight collaborate closely to meet growing tax obligations more effectively.
Source: Fuse Wire

Bibliography

1. https://erpsoftwareblog.com/2025/11/exploring-new-avalara-integration-with-microsoft-outlook-a-giant-step-toward-embedded-compliance/ – Please view link – unable to able to access data
2. https://www.avalara.com/blog/en/north-america/2025/09/avalara-introduces-agentic-ai.html – Avalara has introduced Agentic Tax and Compliance™, a transformative approach that embeds AI agents directly into business systems to automate compliance tasks. This innovation leverages the Avalara LLM Framework for Agentic Applications (ALFA), integrating enterprise LLMs with data isolation, Model Context Protocol (MCP) servers, and AI agents to execute real-time compliance tasks across various platforms, including ERPs, e-commerce platforms, and email clients like Outlook. The goal is to reduce manual effort, increase accuracy, and bring compliance into everyday tools, streamlining workflows and enhancing decision-making processes.