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+# Pi-Inspired Personal Assistant Memory — Implementation Plan
+
+> **For Claude:** REQUIRED SUB-SKILL: Use superpowers:executing-plans to implement this plan task-by-task.
+
+**Goal:** Add two-tier personal-assistant memory: a unified `user/*` namespace shared across channels and a working-memory layer (`user/working`) that survives restarts and is injected at session start.
+
+**Architecture:** `user/working` is written on every compaction (TTL-based flat file with header metadata). On the first message of a new session, `user/profile` and `user/working` are injected into the base system prompt once. All behavior is behind a `memory.user_namespace` config key; when unset the feature is entirely inert.
+
+**Tech Stack:** TypeScript, Vitest, existing `MemoryStore` (`src/memory/store.ts`), `AgentOrchestrator` (`src/backends/native/orchestrator.ts`), Zod config schema
+
+---
+
+## Task 1: Config schema — new memory fields
+
+**Files:**
+- Modify: `src/config/schema.ts:592-613`
+
+Add four new fields to `memorySchema`. They must come before `.default({})` at line 613.
+
+**Step 1: Write the failing type check**
+
+Run:
+```bash
+pnpm typecheck
+```
+Expected: passes (baseline). We'll check again after the edit.
+
+**Step 2: Add fields to memorySchema**
+
+In `src/config/schema.ts`, inside `memorySchema` (after `qmd: qmdSchema,` on line 612, before `}).default({});`), add:
+
+```typescript
+  /**
+   * When set, all channels share user/* memory (unified identity namespace).
+   * Absent = current session-scoped behavior, unchanged.
+   */
+  user_namespace: z.string().optional(),
+  /** How long working memory remains valid after the last compaction (days). */
+  working_memory_ttl_days: z.number().min(1).max(365).default(14),
+  /** Token budget for working memory injection at session start. */
+  working_memory_max_tokens: z.number().min(100).max(4000).default(1000),
+  /** When true, instruct the model to acknowledge prior context on session start. */
+  proactive_session_greeting: z.boolean().default(false),
+```
+
+**Step 3: Run typecheck**
+
+```bash
+pnpm typecheck
+```
+Expected: no errors.
+
+**Step 4: Commit**
+
+```bash
+git add src/config/schema.ts
+git commit -m "feat(memory): add user_namespace and working memory config fields"
+```
+
+---
+
+## Task 2: WorkingMemory module
+
+**Files:**
+- Create: `src/memory/workingMemory.ts`
+- Create: `src/memory/workingMemory.test.ts`
+
+Working memory file format (stored at `{ns}/working.md`):
+
+```
+# Working Memory
+Updated: 2026-02-25T11:30:00Z
+Expires: 2026-03-10T11:30:00Z
+
+[content]
+```
+
+**Step 1: Write the failing tests**
+
+Create `src/memory/workingMemory.test.ts`:
+
+```typescript
+import { describe, it, expect, beforeEach } from 'vitest';
+import { join } from 'path';
+import { mkdtempSync, rmSync } from 'fs';
+import { tmpdir } from 'os';
+import { MemoryStore } from './store.js';
+import { writeWorkingMemory, readWorkingMemory } from './workingMemory.js';
+
+function makeStore(): { store: MemoryStore; dir: string } {
+  const dir = mkdtempSync(join(tmpdir(), 'wm-test-'));
+  const store = new MemoryStore({ dir, maxContextTokens: 2000 });
+  return { store, dir };
+}
+
+describe('writeWorkingMemory', () => {
+  it('writes a file with Updated/Expires headers', () => {
+    const { store, dir } = makeStore();
+    writeWorkingMemory(store, 'user/working', 'some content', 14, 1000);
+    const raw = store.read('user/working');
+    expect(raw).toContain('# Working Memory');
+    expect(raw).toContain('Updated:');
+    expect(raw).toContain('Expires:');
+    expect(raw).toContain('some content');
+    rmSync(dir, { recursive: true });
+  });
+
+  it('truncates content to token budget', () => {
+    const { store, dir } = makeStore();
+    const longContent = 'x'.repeat(10000);
+    writeWorkingMemory(store, 'user/working', longContent, 14, 100);
+    const raw = store.read('user/working');
+    // 100 tokens * 4 chars = 400 chars budget for content
+    const contentPart = raw.split('\n\n').slice(1).join('\n\n');
+    expect(contentPart.length).toBeLessThanOrEqual(400 + 10); // small tolerance
+    rmSync(dir, { recursive: true });
+  });
+});
+
+describe('readWorkingMemory', () => {
+  it('returns null when file does not exist', () => {
+    const { store, dir } = makeStore();
+    expect(readWorkingMemory(store, 'user/working')).toBeNull();
+    rmSync(dir, { recursive: true });
+  });
+
+  it('returns content when not expired', () => {
+    const { store, dir } = makeStore();
+    writeWorkingMemory(store, 'user/working', 'hello world', 14, 1000);
+    const result = readWorkingMemory(store, 'user/working');
+    expect(result).not.toBeNull();
+    expect(result!.content).toBe('hello world');
+    rmSync(dir, { recursive: true });
+  });
+
+  it('returns null when expired', () => {
+    const { store, dir } = makeStore();
+    // Write with 0 TTL days (expires immediately)
+    writeWorkingMemory(store, 'user/working', 'stale content', 0, 1000);
+    const result = readWorkingMemory(store, 'user/working');
+    expect(result).toBeNull();
+    rmSync(dir, { recursive: true });
+  });
+
+  it('returns null for malformed file', () => {
+    const { store, dir } = makeStore();
+    store.write('user/working', 'no headers here', 'replace');
+    expect(readWorkingMemory(store, 'user/working')).toBeNull();
+    rmSync(dir, { recursive: true });
+  });
+});
+```
+
+**Step 2: Run test to verify it fails**
+
+```bash
+pnpm test:run src/memory/workingMemory.test.ts
+```
+Expected: FAIL — module not found.
+
+**Step 3: Implement `src/memory/workingMemory.ts`**
+
+```typescript
+import type { MemoryStore } from './store.js';
+
+export interface WorkingMemoryEntry {
+  content: string;
+  updatedAt: Date;
+  expiresAt: Date;
+}
+
+const HEADER_PREFIX = '# Working Memory\n';
+
+/**
+ * Write a compaction summary to the working memory namespace.
+ * Content is capped at maxTokens (estimated at 4 chars/token).
+ * The file format includes Updated/Expires timestamps for lazy expiry checks.
+ */
+export function writeWorkingMemory(
+  store: MemoryStore,
+  namespace: string,
+  content: string,
+  ttlDays: number,
+  maxTokens: number,
+): void {
+  const now = new Date();
+  const expiresAt = new Date(now.getTime() + ttlDays * 24 * 60 * 60 * 1000);
+  const maxChars = maxTokens * 4;
+  const truncatedContent = content.length > maxChars ? content.slice(0, maxChars) : content;
+
+  const file = [
+    '# Working Memory',
+    `Updated: ${now.toISOString()}`,
+    `Expires: ${expiresAt.toISOString()}`,
+    '',
+    truncatedContent,
+  ].join('\n');
+
+  store.write(namespace, file, 'replace');
+}
+
+/**
+ * Read working memory. Returns null if the file is absent, malformed, or expired.
+ * Expiry is checked lazily here — no background cleanup needed.
+ */
+export function readWorkingMemory(
+  store: MemoryStore,
+  namespace: string,
+): WorkingMemoryEntry | null {
+  const raw = store.read(namespace);
+  if (!raw) {
+    return null;
+  }
+
+  if (!raw.startsWith(HEADER_PREFIX)) {
+    return null;
+  }
+
+  const lines = raw.split('\n');
+  let updatedAt: Date | null = null;
+  let expiresAt: Date | null = null;
+  let contentStartLine = 0;
+
+  for (let i = 1; i < lines.length; i++) {
+    const line = lines[i];
+    if (line.startsWith('Updated: ')) {
+      updatedAt = new Date(line.slice('Updated: '.length));
+    } else if (line.startsWith('Expires: ')) {
+      expiresAt = new Date(line.slice('Expires: '.length));
+    } else if (line === '' && expiresAt !== null) {
+      contentStartLine = i + 1;
+      break;
+    }
+  }
+
+  if (!updatedAt || !expiresAt || isNaN(expiresAt.getTime())) {
+    return null;
+  }
+
+  if (expiresAt.getTime() <= Date.now()) {
+    console.debug('[Flynn:working-memory] Working memory expired, skipping injection');
+    return null;
+  }
+
+  const content = lines.slice(contentStartLine).join('\n').trim();
+
+  return { content, updatedAt, expiresAt };
+}
+```
+
+**Step 4: Run tests**
+
+```bash
+pnpm test:run src/memory/workingMemory.test.ts
+```
+Expected: all pass.
+
+**Step 5: Typecheck**
+
+```bash
+pnpm typecheck
+```
+Expected: no errors.
+
+**Step 6: Commit**
+
+```bash
+git add src/memory/workingMemory.ts src/memory/workingMemory.test.ts
+git commit -m "feat(memory): add working memory read/write with TTL expiry"
+```
+
+---
+
+## Task 3: PA-focused compaction prompt
+
+**Files:**
+- Modify: `src/backends/native/prompts.ts`
+
+The existing `COMPACTION_SYSTEM_PROMPT` is a generic summarizer. We need a personal-assistant variant that captures what the user was working on, decisions made, expressed preferences, and open threads.
+
+**Step 1: Add the new prompt constant**
+
+In `src/backends/native/prompts.ts`, after `COMPACTION_SYSTEM_PROMPT`, add:
+
+```typescript
+/**
+ * Personal-assistant variant of the compaction prompt.
+ * Used when `memory.user_namespace` is configured.
+ * Captures continuity context: what the user was working on, decisions,
+ * preferences, and open threads — not just a generic recap.
+ */
+export const PA_COMPACTION_SYSTEM_PROMPT = `You are summarising a conversation for a personal assistant. Your summary will be injected at the start of the next session so the assistant can pick up exactly where things left off.
+
+Focus on:
+- What the user was working on and its current status (be specific: which files, commands, or steps were involved)
+- Decisions made and why (include rationale when stated)
+- Preferences or constraints the user expressed (tools, styles, approaches to avoid or prefer)
+- Open threads, unresolved questions, or explicit follow-up items
+
+Rules:
+- Preserve key facts, file paths, error messages, and specific values verbatim.
+- Be concise but complete — aim for roughly 20% of the original length.
+- Use bullet points under short descriptive headings.
+- Never invent information not present in the conversation.
+- Skip purely transient content (one-off commands, status messages with no lasting significance).
+
+Output format:
+Return a markdown summary. No preamble — output only the summary.`;
+```
+
+**Step 2: Typecheck**
+
+```bash
+pnpm typecheck
+```
+Expected: no errors.
+
+**Step 3: Commit**
+
+```bash
+git add src/backends/native/prompts.ts
+git commit -m "feat(memory): add personal-assistant compaction prompt"
+```
+
+---
+
+## Task 4: Thread working memory through compaction
+
+**Files:**
+- Modify: `src/context/compaction.ts`
+
+Add `summary` to `CompactionResult` so the orchestrator can write it to `user/working` without re-computing it. Also thread the PA prompt option.
+
+**Step 1: Write the failing test**
+
+There is no direct unit test for `compactHistory()` currently (it requires a live orchestrator). We'll test via the orchestrator integration in Task 5. For now, just verify the type change works.
+
+**Step 2: Update `CompactionResult` interface**
+
+In `src/context/compaction.ts`, add `summary` to `CompactionResult`:
+
+```typescript
+export interface CompactionResult {
+  /** The compacted messages: [summary, ...recentMessages]. */
+  messages: Message[];
+  /** Number of messages that were compacted (removed). */
+  compactedCount: number;
+  /** Estimated tokens before compaction. */
+  tokensBefore: number;
+  /** Estimated tokens after compaction. */
+  tokensAfter: number;
+  /** The raw summary text produced by the compaction model (populated when compaction ran). */
+  summary?: string;
+}
+```
+
+**Step 3: Add `usePersonalAssistantPrompt` option and populate `summary`**
+
+Update the `compactHistory` function signature to accept the option and return the summary:
+
+```typescript
+export async function compactHistory(opts: {
+  messages: Message[];
+  orchestrator: AgentOrchestrator;
+  config: CompactionConfig;
+  memoryStore?: MemoryStore;
+  autoExtract?: boolean;
+  usePersonalAssistantPrompt?: boolean;   // ← new
+}): Promise<CompactionResult> {
+```
+
+In the body, replace the `COMPACTION_SYSTEM_PROMPT` reference in the `orchestrator.delegate()` call:
+
+```typescript
+import { COMPACTION_SYSTEM_PROMPT, MEMORY_EXTRACTION_PROMPT, PA_COMPACTION_SYSTEM_PROMPT } from '../backends/native/prompts.js';
+
+// ...inside compactHistory, where orchestrator.delegate is called:
+const systemPrompt = opts.usePersonalAssistantPrompt
+  ? PA_COMPACTION_SYSTEM_PROMPT
+  : COMPACTION_SYSTEM_PROMPT;
+
+const result = await orchestrator.delegate({
+  task: 'compaction',
+  tier,
+  systemPrompt,
+  message: formattedConversation,
+  maxTokens: config.summaryMaxTokens,
+});
+```
+
+And populate `summary` in the return value:
+
+```typescript
+  return {
+    messages: [...preservedMessages, summaryMessage, ...toKeep],
+    compactedCount: toSummarize.length,
+    tokensBefore: estimateMessageTokens(messages),
+    tokensAfter: estimateMessageTokens([...preservedMessages, summaryMessage, ...toKeep]),
+    summary: result.content,   // ← new
+  };
+```
+
+**Step 4: Typecheck**
+
+```bash
+pnpm typecheck
+```
+Expected: no errors.
+
+**Step 5: Run full test suite**
+
+```bash
+pnpm test:run
+```
+Expected: all pass (summary field is additive, existing tests unaffected).
+
+**Step 6: Commit**
+
+```bash
+git add src/context/compaction.ts src/backends/native/prompts.ts
+git commit -m "feat(memory): thread summary and PA prompt through compaction result"
+```
+
+---
+
+## Task 5: Orchestrator — session-start injection + post-compaction write
+
+**Files:**
+- Modify: `src/backends/native/orchestrator.ts`
+
+This task has two parts:
+1. Write working memory after every compaction (when `userNamespace` is set)
+2. Inject `user/profile` + `user/working` into the base system prompt on first message
+
+**Step 1: Write the failing test — post-compaction working memory write**
+
+In `src/backends/native/orchestrator.test.ts` (or the closest existing test file — check with `ls src/backends/native/*.test.ts`), add a test. First, find the test file:
+
+```bash
+ls src/backends/native/*.test.ts
+```
+
+If `orchestrator.test.ts` exists, add to it. The test should verify that after calling `compact()`, the working memory namespace contains the summary. Because this requires a functioning orchestrator setup, write an integration-style test using vitest mocks rather than a full live model:
+
+Locate the `describe('compact')` block in `src/backends/native/orchestrator.test.ts`. Add:
+
+```typescript
+it('writes summary to user/working when userNamespace is set', async () => {
+  // Setup: orchestrator with a mock delegate that returns a fixed summary
+  // and a real MemoryStore in a temp dir
+  // (follow the existing orchestrator test setup patterns)
+  // After orchestrator.compact(), read store.read('user/working')
+  // Expect it to contain the summary content
+});
+```
+
+You'll need to examine the existing test setup patterns carefully before writing the full test body. See the file for the existing mock structure.
+
+**Step 2: Add new fields to `OrchestratorConfig`**
+
+In `src/backends/native/orchestrator.ts`, in `OrchestratorConfig` (after `attachmentCollector` on line ~160), add:
+
+```typescript
+  /** Shared identity namespace for cross-channel memory (e.g. 'user'). Absent = session-scoped. */
+  userNamespace?: string;
+  /** TTL in days for working memory. Defaults to 14. */
+  workingMemoryTtlDays?: number;
+  /** Token budget for working memory injection. Defaults to 1000. */
+  workingMemoryMaxTokens?: number;
+  /** When true, instruct the model to acknowledge prior context on session start. */
+  proactiveSessionGreeting?: boolean;
+```
+
+**Step 3: Store new config fields on the class**
+
+In the `AgentOrchestrator` class, add private fields (near the other `_memory*` fields):
+
+```typescript
+private _userNamespace?: string;
+private _workingMemoryTtlDays: number;
+private _workingMemoryMaxTokens: number;
+private _proactiveSessionGreeting: boolean;
+private _sessionContextInjected = false;
+```
+
+In the constructor, after the existing memory field assignments:
+
+```typescript
+this._userNamespace = config.userNamespace;
+this._workingMemoryTtlDays = config.workingMemoryTtlDays ?? 14;
+this._workingMemoryMaxTokens = config.workingMemoryMaxTokens ?? 1000;
+this._proactiveSessionGreeting = config.proactiveSessionGreeting ?? false;
+```
+
+**Step 4: Post-compaction write in `compact()`**
+
+Import `writeWorkingMemory` at the top of orchestrator.ts:
+
+```typescript
+import { writeWorkingMemory } from '../../memory/workingMemory.js';
+```
+
+In the `compact()` method, after the `auditLogger?.sessionCompact(...)` call (around line 500), add:
+
+```typescript
+    // Write working memory when user namespace is configured
+    if (result.summary && this._userNamespace && this._memoryStore) {
+      const workingNs = `${this._userNamespace}/working`;
+      writeWorkingMemory(
+        this._memoryStore,
+        workingNs,
+        result.summary,
+        this._workingMemoryTtlDays,
+        this._workingMemoryMaxTokens,
+      );
+      console.log(`[Flynn:working-memory] Updated ${workingNs} after compaction`);
+    }
+```
+
+Also, pass `usePersonalAssistantPrompt` to `compactHistory()` in `compact()`:
+
+```typescript
+    const result = await compactHistory({
+      messages,
+      orchestrator: this,
+      config,
+      memoryStore: this._memoryStore,
+      autoExtract: this._memoryAutoExtract,
+      usePersonalAssistantPrompt: Boolean(this._userNamespace),  // ← new
+    });
+```
+
+**Step 5: Session-start injection**
+
+Add `_injectSessionContext()` private method to `AgentOrchestrator` (after `_injectMemoryContext`):
+
+```typescript
+  private _injectSessionContext(): void {
+    if (this._sessionContextInjected) {
+      return;
+    }
+    this._sessionContextInjected = true;
+
+    if (!this._memoryStore || !this._userNamespace) {
+      return;
+    }
+
+    const sections: string[] = [];
+
+    // User profile block
+    const profile = this._memoryStore.read(`${this._userNamespace}/profile`);
+    if (profile.length > 0) {
+      sections.push(`--- Who you're talking to ---\n${profile}`);
+    }
+
+    // Working memory block
+    const working = readWorkingMemory(this._memoryStore, `${this._userNamespace}/working`);
+    if (working) {
+      sections.push(`--- Recent context ---\n${working.content}`);
+    }
+
+    if (sections.length === 0) {
+      return;
+    }
+
+    this._systemPromptBase = `${this._systemPromptBase}\n\n${sections.join('\n\n')}`;
+
+    if (this._proactiveSessionGreeting) {
+      this._systemPromptBase +=
+        '\n\n[If relevant, briefly acknowledge what the user was last working on before responding to their first message.]';
+    }
+  }
+```
+
+Add the import at the top of orchestrator.ts:
+
+```typescript
+import { writeWorkingMemory, readWorkingMemory } from '../../memory/workingMemory.js';
+```
+
+**Step 6: Call `_injectSessionContext()` from `process()`**
+
+In the `process()` method, find the first place where `_injectMemoryContext()` is called. Add `_injectSessionContext()` just before it:
+
+```typescript
+    // One-time session-start context injection (user/profile + user/working)
+    this._injectSessionContext();
+    this._injectMemoryContext(userMessage);
+```
+
+Also reset `_sessionContextInjected` in `reset()`:
+
+```typescript
+  reset(): void {
+    this._agent.reset();
+    this._usageByTier.clear();
+    this._lastContextAlertLevel = null;
+    this._pendingContextAlert = undefined;
+    this._lastCheckpointAt = 0;
+    this._sessionContextInjected = false;   // ← add
+  }
+```
+
+**Step 7: Typecheck**
+
+```bash
+pnpm typecheck
+```
+Expected: no errors.
+
+**Step 8: Run full test suite**
+
+```bash
+pnpm test:run
+```
+Expected: all pass.
+
+**Step 9: Commit**
+
+```bash
+git add src/backends/native/orchestrator.ts src/memory/workingMemory.ts
+git commit -m "feat(memory): inject session context and write working memory after compaction"
+```
+
+---
+
+## Task 6: Daemon routing — wire new config fields
+
+**Files:**
+- Modify: `src/daemon/routing.ts`
+
+**Step 1: Add the new fields after `memoryDailyLogMaxAssistantChars`**
+
+In `src/daemon/routing.ts` around line 756, after:
+```typescript
+        memoryDailyLogMaxAssistantChars: deps.config.memory?.daily_log?.max_assistant_chars,
+```
+
+Add:
+```typescript
+        userNamespace: deps.config.memory?.user_namespace,
+        workingMemoryTtlDays: deps.config.memory?.working_memory_ttl_days,
+        workingMemoryMaxTokens: deps.config.memory?.working_memory_max_tokens,
+        proactiveSessionGreeting: deps.config.memory?.proactive_session_greeting,
+```
+
+**Step 2: Typecheck**
+
+```bash
+pnpm typecheck
+```
+Expected: no errors.
+
+**Step 3: Run full test suite**
+
+```bash
+pnpm test:run
+```
+Expected: all pass.
+
+**Step 4: Commit**
+
+```bash
+git add src/daemon/routing.ts
+git commit -m "feat(memory): wire user_namespace and working memory config to orchestrator"
+```
+
+---
+
+## Task 7: Smoke test and state.json update
+
+**Step 1: Run full test suite one final time**
+
+```bash
+pnpm test:run
+```
+Expected: all pass.
+
+**Step 2: Manual smoke test (optional but recommended)**
+
+Add this to your `config.yaml`:
+```yaml
+memory:
+  user_namespace: "user"
+  working_memory_ttl_days: 14
+  working_memory_max_tokens: 1000
+  proactive_session_greeting: false
+```
+
+Start a session, chat for a while, trigger a compaction (or wait for auto-compaction), then restart and start a new session. Verify `user/working.md` exists in your memory dir and is injected on the new session's first turn.
+
+**Step 3: Update state.json**
+
+In `docs/plans/state.json`, add an entry to `completed`:
+
+```json
+"pi_personal_assistant_memory": {
+  "status": "complete",
+  "commit": "<sha>",
+  "summary": "Two-tier personal assistant memory: working memory (user/working, TTL-based) written on compaction, injected at session start; unified user/* namespace across channels; PA-focused compaction prompt; proactive session greeting option."
+}
+```
+
+**Step 4: Final commit**
+
+```bash
+git add docs/plans/state.json
+git commit -m "docs(state): mark pi personal assistant memory as complete"
+```
+
+---
+
+## Success Criteria Checklist
+
+- [ ] `user_namespace` absent → zero behavior change (all new code paths guarded by `this._userNamespace` check)
+- [ ] After compaction with `user_namespace` set, `user/working.md` exists in memory dir
+- [ ] Daemon restart + new session → `user/working` content appears in the first-turn system prompt
+- [ ] Telegram and web UI sessions share the same `user/working` file
+- [ ] Expired working memory (TTL elapsed) is silently ignored
+- [ ] All existing tests pass
+
+---
+
+## Reference: Config
+
+```yaml
+memory:
+  # Enables shared identity and working memory. Absent = unchanged behavior.
+  user_namespace: "user"
+  working_memory_ttl_days: 14       # default
+  working_memory_max_tokens: 1000   # default
+  proactive_session_greeting: false # default
+```