Planning

TL;DR Regulatory compliance – SOC 2, GDPR, HIPAA, PCI DSS, ISO 27001 – looks impenetrable from the outside. Hundreds of controls, dozens of policy documents, auditor-specific jargon, and no clear starting point. Before you hire a $300/hour consultant or drop $50K on a GRC platform, you can use Claude to do the initial heavy lifting: map which frameworks apply to your business, identify your biggest gaps, draft policies that match your actual infrastructure, build a prioritized remediation plan, and prepare for your first auditor conversation. This post walks through the process I used, with real prompts and outputs, to go from “we probably need SOC 2” to a concrete compliance roadmap in a single afternoon. ...

TL;DR The Jellyfin HA conversion touches a .NET 10 codebase, Entity Framework Core migrations, Kubernetes manifests, Terraform infrastructure, PostgreSQL operations, and FFmpeg transcoding pipelines. No single AI model understands all of this equally well. So I used four of them — the same multi-model planning pattern that shipped dnd-multi in a single day and that I documented in the LLM GitHub PR workflow. This post covers how I adapted that pattern for infrastructure work, what each model caught, and why planning is where all the human time should go. ...

Context: This is the real project plan for dnd-multi, a full-stack AI Dungeon Master platform. It was generated by Claude Opus 4.6 during Phase 0 of the LLM GitHub PR workflow — synthesizing gap analysis from four different models into a structured execution document. Claude Sonnet 4.6 then used this plan overnight to open 24 PRs and ship all seven phases. Personal identifiers have been removed. Technical content is verbatim. Milestone Timeline Milestone Target Date Deliverable M0 — Platform Stable 2026-03-13 All broken deps fixed, migrations applied, Tier 2 lore generating, smoke tests passing M1 — First Playable Session 2026-04-03 Turn structure live, player identity in DM prompt, hot phrase + /dm command working M2 — Full Action Flow 2026-04-24 Action confirmation, non-active player queue, player votes operational M3 — IC/OOC + Personality 2026-05-08 Meta-mode detection, in-character assumption, DM personality tuning deployed M4 — Content & Reporting 2026-05-22 Book/media content generation live, /report + /flag system in admin dashboard M5 — Combat Tracker 2026-06-12 Live HP tracker UI, [COMBAT:] directives wired to death protection M6 — Feature Complete v1.0 2026-06-19 Spell reference Discord command, shareable campaign invitation links Current State Summary The platform has a solid full-stack foundation with all core systems implemented and deployed to the home k3s cluster. The gap is game experience polish — the AI DM has no awareness of whose turn it is, doesn’t distinguish in-character from out-of-character speech, lacks an action confirmation flow, and has no mechanism for players to report misbehavior. These are the features that make the difference between a tech demo and a playable game. ...