AI Tax Planning Memo Agent
Automating Tax Planning Memo Drafting with AI
Structured Authority Research and Citation
The agent maps each tax issue to the full hierarchy of authority—IRC sections, Treasury Regulations, revenue rulings, and case law—then retrieves current primary sources with proper citation formatting and precedential weight assessment.
Risk Grading Against Penalty Standards
Automated analysis evaluates position strength against substantial authority, more-likely-than-not, and reasonable basis thresholds, flagging when Form 8275 or 8275-R disclosure is warranted and noting preparer standard implications under §6694 and Circular 230.
Dual-Output Memo Generation
The system produces both a fully cited internal research memorandum with IRAC/CREAC structure and pin-cites, plus a plain-English client advisory letter with executive summary, risk ratings, action steps, and implementation checklists.
How Cassidy automates tax research requests using AI
Step 1: Trigger on new tax research request
The Workflow activates when a compliance specialist submits an intake form or sends a request through Slack or Teams—capturing taxpayer profile, entity type, tax years, jurisdictions, materiality thresholds, and the specific questions presented.
Step 2: Parse facts and map issues to authority
Cassidy structures the engagement context, identifies data gaps, and maps each issue to the relevant authority hierarchy—flagging applicable IRC sections, Treasury Regulations, IRS guidance, and circuit-specific precedent under the Golsen rule.
Step 3: Research and validate authorities
The Workflow searches the Knowledge Base and connected research sources for primary authorities, retrieves relevant case law with precedential weight notations, and runs citator checks to confirm currentness before analysis.
Step 4: Analyze and grade risk
Cassidy applies IRAC/CREAC legal analysis, evaluates position strength against penalty standards, considers contrary authority and anti-abuse doctrines, and recommends disclosure where positions fall below substantial authority.
Step 5: Draft internal memo and client letter
The Workflow generates two deliverables: a citable internal research memorandum with full citations, pin-cites, and risk assessment, plus a client-facing advisory letter with plain-language conclusions, action items, and deadlines.
Step 6: Human-in-the-Loop review and finalize
A compliance specialist reviews the drafts, resolves any flagged issues, and approves final deliverables—which Cassidy packages with supporting workpapers, authority excerpts, and implementation checklists for matter retention.
Implement it inside your company
- Hands-on onboarding and support
- Self-paced training for your team
- Dedicated implementation experts
- Ongoing use case discovery
- ROI tracking & analytics dashboards
- Proven playbooks to get started fast
