feat(ask): persistent conversations, history & per-brief follow-ups

apps/api/src/index.ts

@@ -29,6 +29,7 @@ import { registerCompareRoutes } from './routes/compare.js';
 import { registerHabitRoutes } from './routes/habits.js';
 import { registerInsightsRoutes } from './routes/insights.js';
 import { registerAskRoutes } from './routes/ask.js';
+import { registerConversationRoutes } from './routes/conversations.js';
 import { registerSyncRoutes } from './routes/sync.js';
 import { registerIngestRoutes } from './routes/ingest.js';
 import { registerAuthRoutes } from './routes/auth.js';
@@ -86,6 +87,7 @@ async function main() {
   await app.register(registerHabitRoutes, { prefix: '/api' });
   await app.register(registerInsightsRoutes, { prefix: '/api' });
   await app.register(registerAskRoutes, { prefix: '/api' });
+  await app.register(registerConversationRoutes, { prefix: '/api' });
   await app.register(registerSyncRoutes, { prefix: '/api' });
   await app.register(registerIngestRoutes, { prefix: '/api' });
   await app.register(registerAuthRoutes, { prefix: '/api' });

apps/api/src/routes/ask.ts

@@ -1,25 +1,70 @@
 import type { FastifyPluginAsync } from 'fastify';
 import { schemas } from '@vcc/shared';
+import { queries } from '@vcc/db';
 import type { z } from 'zod';
 import { answerQuestion } from '../services/localAsk.js';
 
+/** Derive a short thread title from the opening question. */
+function titleFrom(question: string): string {
+  const t = question.trim().replace(/\s+/g, ' ');
+  return t.length > 70 ? `${t.slice(0, 67)}…` : t;
+}
+
 /**
  * Free-form Q&A answered by the on-box AI CLI (claude -p → codex fallback) over
- * the user's recent data. Keeps the SSE contract the web client expects, but the
- * CLI is non-streaming so the answer arrives as a single `data:` event.
+ * the user's recent data. The exchange is PERSISTED to a conversation so the
+ * user can revisit it and ask follow-ups; the conversation id is returned in the
+ * `X-Conversation-Id` response header. Keeps the SSE contract the web client
+ * expects — the CLI is non-streaming so the answer arrives as a single event.
  */
 export const registerAskRoutes: FastifyPluginAsync = async (app) => {
   app.post('/ask', { schema: { body: schemas.askSchema } }, async (req, reply) => {
     const body = req.body as z.infer<typeof schemas.askSchema>;
+    const db = req.server.db;
+
+    // Resolve (or open) the thread this question belongs to.
+    let conversation = body.conversationId ? queries.conversations.meta(db, body.conversationId) : null;
+    let anchorBrief: string | null = null;
+    if (!conversation) {
+      let anchorBriefId: string | null = null;
+      let anchorDate: string | null = null;
+      if (body.anchorBriefDate) {
+        const brief = queries.briefings.latestOfType(db, 'daily', body.anchorBriefDate);
+        if (brief) {
+          anchorBriefId = brief.id;
+          anchorDate = brief.date;
+          anchorBrief = brief.content;
+        }
+      }
+      conversation = queries.conversations.create(db, {
+        title: titleFrom(body.question),
+        anchorBriefId,
+        anchorDate,
+      });
+    } else if (conversation.anchorBriefId) {
+      anchorBrief = queries.briefings.byId(db, conversation.anchorBriefId)?.content ?? null;
+    }
+
+    // Prior turns (before persisting this one) feed the follow-up context.
+    const history = queries.conversations
+      .messages(db, conversation.id)
+      .map((m) => ({ role: m.role, content: m.content }));
+    queries.conversations.addMessage(db, conversation.id, 'user', body.question);
+
     reply.raw.setHeader('Content-Type', 'text/event-stream');
     reply.raw.setHeader('Cache-Control', 'no-cache, no-transform');
     reply.raw.setHeader('Connection', 'keep-alive');
     reply.raw.setHeader('X-Accel-Buffering', 'no');
+    reply.raw.setHeader('X-Conversation-Id', conversation.id);
     reply.hijack();
 
     try {
-      const { text, cli } = await answerQuestion(req.server.db, body.question, body.context?.date);
-      req.log.info({ cli }, 'ask answered');
+      const { text, cli } = await answerQuestion(db, body.question, body.context?.date, {
+        history,
+        anchorBrief,
+      });
+      queries.conversations.addMessage(db, conversation.id, 'assistant', text);
+      req.log.info({ cli, conversationId: conversation.id }, 'ask answered');
       reply.raw.write(`data: ${JSON.stringify({ text })}\n\n`);
       reply.raw.write('data: [DONE]\n\n');
       reply.raw.end();

apps/api/src/routes/conversations.ts

@@ -0,0 +1,25 @@
+import type { FastifyPluginAsync } from 'fastify';
+import { queries } from '@vcc/db';
+import { ok, fail } from '../lib/envelope.js';
+
+/** Persisted Ask AI conversations — list, read, delete (for the history drawer). */
+export const registerConversationRoutes: FastifyPluginAsync = async (app) => {
+  app.get('/conversations', async (req) => {
+    const { limit } = req.query as { limit?: string };
+    const n = Math.min(Math.max(Number(limit) || 30, 1), 100);
+    return ok(queries.conversations.list(req.server.db, n));
+  });
+
+  app.get('/conversations/:id', async (req, reply) => {
+    const { id } = req.params as { id: string };
+    const conv = queries.conversations.get(req.server.db, id);
+    if (!conv) return reply.status(404).send(fail('conversation not found', 'NOT_FOUND'));
+    return ok(conv);
+  });
+
+  app.delete('/conversations/:id', async (req) => {
+    const { id } = req.params as { id: string };
+    queries.conversations.remove(req.server.db, id);
+    return ok({ deleted: true });
+  });
+};

apps/api/src/routes/insights.ts

@@ -22,6 +22,14 @@ export const registerInsightsRoutes: FastifyPluginAsync = async (app) => {
     return ok(computeWeeklySummary(req.server.db, end || todayIso()));
   });
 
+  // Recent daily briefs, newest first — includes prior regenerations (each is
+  // its own row) so the history shows older versions too.
+  app.get('/insights/briefings', async (req) => {
+    const { limit } = req.query as { limit?: string };
+    const n = Math.min(Math.max(Number(limit) || 30, 1), 100);
+    return ok(queries.briefings.listRecent(req.server.db, 'daily', n));
+  });
+
   app.get('/insights/briefing/:date', async (req, reply) => {
     const { date } = req.params as { date: string };
     const briefing = queries.briefings.latestOfType(req.server.db, 'daily', date);

apps/api/src/services/localAsk.ts

@@ -17,12 +17,43 @@ Rules:
 - Do not use any tools or run commands; answer from the provided data only.
 - Workouts/runs may be tracked elsewhere (e.g. Strava) and absent here; for training questions reason from recovery + steps.`;
 
+export interface AskOptions {
+  /** Prior turns in this thread (oldest → newest), for follow-up context. */
+  history?: { role: 'user' | 'assistant'; content: string }[];
+  /** A daily brief this thread is anchored to — fed as additional context. */
+  anchorBrief?: string | null;
+}
+
 export async function answerQuestion(
   db: Database,
   question: string,
   date?: string,
+  opts: AskOptions = {},
 ): Promise<{ text: string; cli: 'claude' | 'codex' }> {
   const context = buildBriefContext(db, date ?? todayIso());
-  const prompt = `${ASK_SYSTEM}\n\n## About the user\n${getUserProfile()}\n\n---\nHEALTH DATA:\n${context}\n\n---\nQUESTION: ${question}\n\nAnswer:`;
-  return runAgent(prompt, { cli: process.env.ASK_CLI as 'claude' | 'codex' | undefined });
+
+  const parts = [
+    ASK_SYSTEM,
+    `\n\n## About the user\n${getUserProfile()}`,
+    `\n\n---\nHEALTH DATA:\n${context}`,
+  ];
+
+  if (opts.anchorBrief) {
+    parts.push(
+      `\n\n---\nEARLIER DAILY BRIEF (the user is asking a follow-up about this brief):\n${opts.anchorBrief}`,
+    );
+  }
+
+  // Keep the last few turns so follow-ups have context without an unbounded prompt.
+  const history = (opts.history ?? []).slice(-8);
+  if (history.length) {
+    const transcript = history
+      .map((m) => `${m.role === 'user' ? 'User' : 'Assistant'}: ${m.content}`)
+      .join('\n\n');
+    parts.push(`\n\n---\nCONVERSATION SO FAR:\n${transcript}`);
+  }
+
+  parts.push(`\n\n---\nQUESTION: ${question}\n\nAnswer:`);
+
+  return runAgent(parts.join(''), { cli: process.env.ASK_CLI as 'claude' | 'codex' | undefined });
 }

apps/web/src/components/ask/AskClaude.tsx

@@ -1,10 +1,14 @@
-import { useEffect, useId, useLayoutEffect, useRef, useState } from 'react';
+import { useCallback, useEffect, useId, useLayoutEffect, useRef, useState } from 'react';
+import { useLocation } from 'react-router-dom';
 import clsx from 'clsx';
 import { useAsk } from '../../hooks/useAsk.js';
 import { useHealthData } from '../../hooks/useHealthData.js';
 import { deriveReadiness } from '../../lib/readiness.js';
+import { getConversation } from '../../lib/api.js';
+import { fmtDate } from '../../lib/formatters.js';
 import { Markdown } from '../shared/Markdown.js';
 import { AskAvatar, AskGreeting, CHIPS, GROUNDING_NOTE } from './AskShell.js';
+import { ConversationHistory } from './ConversationHistory.js';
 import { IconSend } from '../shared/icons.js';
 
 interface Message {
@@ -32,13 +36,54 @@ export function AskClaude() {
   const { ask, answer, typing, pending, error, stop } = useAsk();
   const [messages, setMessages] = useState<Message[]>([]);
   const [draft, setDraft] = useState('');
+  // The persisted thread these messages belong to (null until the first reply).
+  const [conversationId, setConversationId] = useState<string | null>(null);
+  // A daily brief this thread follows up on, when arriving via "Discuss".
+  const [anchorDate, setAnchorDate] = useState<string | undefined>(undefined);
+  const [historyOpen, setHistoryOpen] = useState(false);
+  const [historyKey, setHistoryKey] = useState(0);
   // The assistant message currently receiving streamed tokens.
   const streamingId = useRef<string | null>(null);
   const scrollAnchor = useRef<HTMLDivElement>(null);
   const inputId = useId();
+  const location = useLocation();
 
   const started = messages.length > 0;
 
+  // Arriving from a brief's "Discuss" button: start a fresh thread anchored to
+  // that brief. location.key changes on every navigation so re-clicking works.
+  const incomingAnchor = (location.state as { anchorBriefDate?: string } | null)?.anchorBriefDate;
+  useEffect(() => {
+    if (!incomingAnchor) return;
+    stop();
+    setMessages([]);
+    setConversationId(null);
+    setAnchorDate(incomingAnchor);
+    // Clear nav state so a refresh doesn't re-anchor.
+    window.history.replaceState({}, '');
+  }, [incomingAnchor, location.key, stop]);
+
+  const newChat = useCallback(() => {
+    stop();
+    setMessages([]);
+    setConversationId(null);
+    setAnchorDate(undefined);
+    setDraft('');
+  }, [stop]);
+
+  const loadConversation = useCallback(
+    async (id: string) => {
+      setHistoryOpen(false);
+      const conv = await getConversation(id);
+      stop();
+      streamingId.current = null;
+      setConversationId(conv.id);
+      setAnchorDate(conv.anchorDate ?? undefined);
+      setMessages(conv.messages.map((m) => ({ id: m.id, role: m.role, text: m.content })));
+    },
+    [stop],
+  );
+
   // Mirror streamed tokens into the in-flight assistant message as they arrive.
   useEffect(() => {
     const id = streamingId.current;
@@ -79,18 +124,49 @@ export function AskClaude() {
       { id: assistantId, role: 'assistant', text: '' },
     ]);
     setDraft('');
-    ask(question);
+    const startingNew = !conversationId;
+    ask(question, {
+      conversationId: conversationId ?? undefined,
+      // Anchor only applies to the first message of a brand-new anchored thread.
+      anchorBriefDate: conversationId ? undefined : anchorDate,
+      onConversationId: (id) => {
+        setConversationId(id);
+        if (startingNew) setHistoryKey((k) => k + 1); // refresh the drawer list
+      },
+    });
   };
 
   return (
     // Fill the scroll viewport so the composer pins to the bottom even on a
     // short conversation. Mobile subtracts the sticky top bar (h-14 + safe area);
     // desktop has no top bar (the rail is the chrome).
     <div className="flex flex-col min-h-[calc(100dvh-3.5rem-env(safe-area-inset-top))] md:min-h-[100dvh]">
+      {/* Control bar — new chat + history */}
+      <div className="flex items-center justify-end gap-2 pt-4 -mb-2">
+        {(started || conversationId) && (
+          <button type="button" className="btn-soft px-3 py-1.5 text-[13px]" onClick={newChat}>
+            New chat
+          </button>
+        )}
+        <button
+          type="button"
+          className="btn-soft px-3 py-1.5 text-[13px]"
+          onClick={() => setHistoryOpen(true)}
+        >
+          History
+        </button>
+      </div>
+
       {/* Greeting */}
-      <header className="pt-9 sm:pt-10 pb-2 animate-fade-rise">
+      <header className="pt-5 pb-2 animate-fade-rise">
         <AskGreeting readiness={readiness} />
-        {!started && (
+        {anchorDate && (
+          <div className="mt-4 inline-flex items-center gap-2 rounded-full bg-accent-wash text-accent-deep px-3.5 py-1.5 text-[12.5px] font-medium">
+            <span className="w-1.5 h-1.5 rounded-full bg-accent" />
+            Following up on your {fmtDate(anchorDate, 'EEE, MMM d')} brief
+          </div>
+        )}
+        {!started && !anchorDate && (
           <div className="flex flex-wrap gap-2.5 mt-6">
             {CHIPS.map((c) => (
               <button
@@ -167,6 +243,14 @@ export function AskClaude() {
         </form>
         <p className="text-center mt-2.5 text-ink-mute text-[11px]">{GROUNDING_NOTE}</p>
       </div>
+
+      <ConversationHistory
+        open={historyOpen}
+        onClose={() => setHistoryOpen(false)}
+        onSelect={loadConversation}
+        activeId={conversationId}
+        reloadKey={historyKey}
+      />
     </div>
   );
 }