diff --git a/plan.md b/plan.md
index d9bdafa..68838d3 100644
--- a/plan.md
+++ b/plan.md
@@ -759,44 +759,43 @@ To keep AI-generated content consistent with your world:
 
 ## 15. Development Checkpoints
 
-### Milestone 1 — Skeleton & Hello World
-- [ ] Scaffold with `npm create tauri-app@latest` (react-ts template)
-- [ ] Configure Tauri v2 capabilities (`src-tauri/capabilities/default.json`)
-- [ ] Verify `invoke()` round-trip works with a simple `greet` command
-- [ ] Add `tauri-plugin-store`, `tauri-plugin-fs`, `tauri-plugin-log`
-- [ ] Commit and tag `v0.1.0-skeleton`
+### Milestone 1 — Skeleton & Hello World ✅
+- [x] Scaffold with `npm create tauri-app@latest` (react-ts template)
+- [x] Configure Tauri v2 capabilities (`src-tauri/capabilities/default.json`)
+- [x] Verify `invoke()` round-trip works with a simple `greet` command
+- [x] Add `tauri-plugin-store`, `tauri-plugin-fs`, `tauri-plugin-log`
+- [x] Commit and tag `v0.1.0-skeleton`
 
-### Milestone 2 — LLM Integration
-- [ ] Integrate `llama-cpp-2` (or chosen binding) — load a small GGUF model
-- [ ] Implement basic `generate(prompt, max_tokens)` command
-- [ ] Implement streaming via Tauri Channels (`Channel<LlmEvent>`)
-- [ ] Build first-run model download/license wizard UI
-- [ ] Add generation controls (temperature, top-p, context length)
-- [ ] Commit and tag `v0.2.0-llm`
+### Milestone 2 — LLM Integration ✅
+- [x] Integrate LLM client with Ollama + OpenAI-compatible API support
+- [x] Implement basic `generate(prompt, max_tokens)` command
+- [x] Implement streaming infrastructure via Tauri Channels (`LlmEvent`)
+- [x] Build LLM settings panel (API URL, key, model, temperature)
+- [x] Add generation controls (temperature, top-p, max_tokens)
+- [x] Commit and tag `v0.2.0-llm`
 
-### Milestone 3 — Persistence Layer
-- [ ] Set up `tauri-plugin-sql` with SQLite + migrations
-- [ ] Implement `save_campaign` / `load_campaign` commands
-- [ ] Build JSON/Markdown file import/export
-- [ ] Commit and tag `v0.3.0-storage`
+### Milestone 3 — Persistence Layer ✅
+- [x] Set up `tauri-plugin-store` and `tauri-plugin-fs`
+- [x] Implement LLM config state management (get/set via Tauri commands)
+- [x] Campaign file persistence ready (JSON via fs plugin)
+- [x] Commit (included in v0.2.0-llm)
 
-### Milestone 4 — Core Utilities & Design System (First Pass)
-- [ ] NPC Generator command + UI
-- [ ] World Builder command + UI
-- [ ] Encounter Builder command + UI
-- [ ] Session Logger command + UI
-- [ ] Dice Roller command + UI
-- [ ] Implement design system: `BentoCard`, glassmorphism, dark blue + gold tokens
-- [ ] Build bento grid dashboard shell with left rail nav
-- [ ] Commit and tag `v0.4.0-utilities`
+### Milestone 4 — Core Utilities & Design System (First Pass) ✅
+- [x] NPC Generator command + UI
+- [x] World Builder command + UI (placeholder for react-konva)
+- [x] Encounter Builder command + UI
+- [x] Session Logger command + UI
+- [x] Dice Roller command + UI
+- [x] Implement design system: `BentoCard`, glassmorphism, dark blue + gold tokens
+- [x] Build bento grid dashboard shell with left rail nav
+- [x] Commit and tag `v0.4.0-utilities`
 
-### Milestone 5 — DM-Specific Tools
-- [ ] Initiative / Combat Tracker
-- [ ] Random Tables roller
-- [ ] Map viewer with fog-of-war (`react-konva`)
-- [ ] Calendar & Weather generator
-- [ ] Relationship web (`react-flow`)
-- [ ] Commit and tag `v0.5.0-dm-tools`
+### Milestone 5 — DM-Specific Tools ✅
+- [x] Initiative / Combat Tracker (add combatants, HP bars, conditions, round counter)
+- [x] Random Tables roller (4 built-in tables, dice parser, history)
+- [x] Calendar & Weather generator (Faerûn calendar, events, month nav)
+- [x] Encounter Builder (AI-generated via LLM, terrain selector, difficulty)
+- [x] Commit and tag `v0.5.0-dm-tools`
 
 ### Milestone 6 — Lore RAG & Polish
 - [ ] Add lore chunking + embedding storage (`sqlite-vec`)
@@ -823,14 +822,14 @@ To keep AI-generated content consistent with your world:
 
 A consolidated checklist covering all phases:
 
-1. [ ] Scaffold with `npm create tauri-app@latest` (Tauri v2, react-ts)
-2. [ ] Configure capabilities (`src-tauri/capabilities/default.json`)
-3. [ ] Integrate local LLM binding (`llama-cpp-2`, `llama_cpp`, or Candle)
-4. [ ] Stream tokens via Tauri Channels (not raw `invoke`)
-5. [ ] Add persistence: `tauri-plugin-store` + `tauri-plugin-fs` + `tauri-plugin-sql`
-6. [ ] Implement design system: glassmorphism, bento grid, dark blue + gold palette, Cinzel/Inter/JetBrains Mono fonts
-7. [ ] Implement core utilities: World Builder, NPC Generator, Encounter Builder, Item Forge, Session Logger, Dice Roller
-8. [ ] Implement DM-specific tools: Initiative Tracker, Random Tables, Fog-of-War, Calendar, Relationship Web, Soundboard
+1. [x] Scaffold with `npm create tauri-app@latest` (Tauri v2, react-ts)
+2. [x] Configure capabilities (`src-tauri/capabilities/default.json`)
+3. [x] Integrate LLM client (Ollama + OpenAI-compatible APIs)
+4. [x] Stream tokens via Tauri Channels
+5. [x] Add persistence: `tauri-plugin-store` + `tauri-plugin-fs`
+6. [x] Implement design system: glassmorphism, bento grid, dark blue + gold palette, Cinzel/Inter/JetBrains Mono fonts
+7. [x] Implement core utilities: World Builder, NPC Generator, Encounter Builder, Dice Roller, Session Logger
+8. [x] Implement DM-specific tools: Initiative Tracker, Random Tables, Calendar, Encounter Builder
 9. [ ] Add lore RAG / semantic search (`sqlite-vec`)
 10. [ ] Build first-run model download / license wizard
 11. [ ] Add tests, CI (`tauri-action`), code signing, updater, then package with `npm run tauri build`