Estate Planning Software Development: Building AI-Powered Tools for Attorneys and Families
How AI makes estate planning accessible — from document generation to plain-language explanations. Lessons from building PlanYourSunset, an estate planning platform for New York.
76% of Americans don’t have a will
It’s not because they don’t care. It’s because the process is expensive ($2,000+ for a complete package with a New York attorney), confusing (what’s a pour-over will? do I need a trust?), and time-consuming (multiple appointments, document gathering, weeks of waiting). These barriers have persisted for decades. AI changes the equation.
We built PlanYourSunset to prove this. It’s an estate planning platform currently focused on New York that combines attorney-reviewed document templates (wills, powers of attorney, healthcare directives) with an AI assistant named Larry who explains legal concepts in plain English, an encrypted digital vault for sensitive documents, and a seamless connection to qualified estate attorneys when human expertise is needed.
The technical challenge: jurisdiction-specific compliance
Estate planning isn’t a generic legal task. Every state has its own requirements for what makes a will valid, how powers of attorney must be structured, and what healthcare directives can include. New York, for example, requires two witnesses for a will (not a notary, as some states allow), has a specific statutory short form for powers of attorney, and has particular rules about healthcare proxies.
This means you can’t build a generic “will maker” and hope it works everywhere. The document generation logic must encode jurisdiction-specific rules, and any AI component must be grounded in the law of the relevant state — not general legal principles that might be wrong in context.
For PlanYourSunset, we made a deliberate choice to start with New York only and do it properly, rather than launch in all 50 states with shallow coverage. Larry, the AI assistant, is grounded specifically in NY law and the platform’s own expert-written Learning Hub. When a user asks about estate planning, the answers reflect NY-specific requirements — not generic advice that might apply in California but be wrong in New York.
This jurisdiction-by-jurisdiction approach is slower to scale but produces a much better product. And it’s a pattern we’d recommend to anyone building legal tech: go deep in one jurisdiction before going wide.
AI as translator, not replacement
The most interesting design decision in PlanYourSunset wasn’t the document generation — it was Larry. We positioned the AI not as a lawyer replacement but as a translator between legal complexity and human understanding.
Users can highlight any part of a legal document and get a plain-language explanation. They can ask questions they’d be embarrassed to ask an attorney (“what happens to my stuff if I don’t have a will?”). Larry helps them prepare better questions for their actual attorney conversations and tracks every question and document request automatically.
This is a subtle but important architectural choice. Larry doesn’t give legal advice — he explains legal concepts using the platform’s own vetted content as the knowledge base. The distinction matters for liability, for user trust, and for the quality of the output. By grounding responses in curated content rather than general LLM knowledge, we avoid the hallucination problems that plague general-purpose legal chatbots.
“The insight that shaped PlanYourSunset was that most people don’t need a cheaper lawyer — they need a translator. Someone who explains what’s happening in language they understand. AI is remarkably good at this when you ground it in the right source material.”
The encrypted vault: security as a feature
Estate planning involves some of the most sensitive documents a person owns — wills, financial account details, insurance policies, property deeds. PlanYourSunset’s vault encrypts everything on the user’s device before upload. The platform never sees the vault password. Access can require N-of-M appointee keys (e.g., 2 of 3 designated heirs must agree to unlock), with a grace period that notifies the owner of access attempts.
This isn’t just a security feature — it solves a real estate planning problem. One of the biggest issues in estate administration is that heirs don’t know where documents are, or can’t access them when they need to. A properly designed digital vault with controlled access and emergency master keys addresses this directly.
Building estate planning software: practical considerations
If you’re considering building in this space, here are the key things we learned.
Document generation requires serious legal review. Templates must be drafted or reviewed by attorneys licensed in the target jurisdiction. The software can help users fill in the right information, but the underlying legal structure needs expert validation. Budget for legal review alongside development.
State-specific expansion is expensive. Each new state means new templates, new legal review, updated AI grounding content, and potentially different user flows (some states require notarisation, others don’t; some have community property rules, others don’t). Plan your expansion strategy carefully.
The attorney connection matters. Most estate situations are straightforward enough for self-service with good templates. But some — blended families, significant assets, business ownership, real estate in multiple states — genuinely need attorney involvement. Building a smooth handoff from self-service to professional advice makes the platform more trustworthy and more useful.
For timeline and budget: building a single-jurisdiction MVP with document generation, basic AI assistant, and secure storage took us roughly 3–4 months. A multi-jurisdiction platform with full attorney integration would be a 6–12 month project at $150K–$400K, depending on scope.
Thinking about building an estate planning platform or legal document tool? Let’s talk — we’ll share what we learned building PlanYourSunset and help you scope your project.