This topic covers AI-enabled tooling and data infrastructure used to calculate taxable events, generate audit-ready reports, and maintain compliance for crypto portfolios. As of 2025, continuing regulatory scrutiny and expanding cross‑chain activity make precise cost-basis, timestamped price feeds, and end-to-end data provenance essential for firms and tax professionals. Key components include market data APIs (for historical prices and token metadata), data pipeline orchestration (for ingesting on‑chain and exchange data), data catalog & lineage (for audit trails and provenance), and spreadsheet automation (for familiar accounting workflows and final reporting). Practical examples: CoinGecko and CoinMarketCap provide REST APIs and MCP (Model Context Protocol) servers that standardize access to price, market-cap, and token identifiers across hundreds of blockchains—critical for mapping trades to fiat values. Nasdaq Data Link MCP exposes traditional financial datasets to LLM-driven tooling, enabling reconciliations between crypto markets and broader market references. Orchestration layers consolidate on‑chain event logs, exchange statements, and OTC fills; cataloging and lineage systems record transformations and source attribution so outputs can withstand tax audits. Spreadsheet automation bridges automated pipelines with accountants’ review workflows, reducing manual reconciliation errors while preserving transparent change histories. When selecting solutions, prioritize broad chain/token coverage, reliable historical pricing, strong provenance and explainability, and integration options (APIs, MCP, or spreadsheet connectors). Given increased enforcement and multi‑jurisdictional reporting complexity, combining market data APIs with robust pipeline orchestration and lineage is now a practical baseline for defensible crypto tax and compliance operations.