v1.8.2: tool loop cap-hit summary + tool call UI compaction

Old hardcoded MAX_TOOL_LOOP_DEPTH=15 replaced by per-agent
max_tool_calls (1-100, AGENTS.md frontmatter) with defaults: 30 for
read-only-only agents, 10 for agents that include any non-read-only
tool, 15 for raw chat. When the loop hits cap, fire one final summary
call with tools disabled, stream the wrap-up into the in-flight
assistant message, then insert a system sentinel with
metadata.kind='cap_hit'. The sentinel renders an amber bubble with a
Continue button (latest sentinel only) that POSTs to a new
/api/chats/:id/continue route to extend. Hard ceiling: 3 cap-hits per
chat (2 continues max) — third sentinel reports can_continue=false.

Error frames carry a machine-readable reason code alongside human
error text. Failed messages persist the reason via
metadata.kind='error' so the bubble renders specifics on reload (WS
error frame is one-shot).

Tool call UI rewired: ToolCallLine renders inline (↳ name args
spinner/check/✗, expand-on-tap for args+result); ToolCallGroup
collapses 3+ consecutive same-tool runs into a compact card.
MessageList owns a three-pass pre-render (flatten + fold tool
results onto matching runs by id + group same-tool runs + number
sentinels). MessageBubble drops tool rendering and adds the
sentinel / error-reason branches. ToolCallCard deleted.

Roadmap follow-up logged: add explicit max_tool_calls: 30 to the 6
agents in /data/AGENTS.md and /opt/boocode/AGENTS.md post-ship for
discoverability (defaults handle behavior identically).

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>

.gitignore

@@ -6,3 +6,4 @@ dist
 .vite
 coverage
 secrets/
+data/

apps/server/src/routes/chats.ts

@@ -231,7 +231,7 @@ export function registerChatRoutes(
           INSERT INTO messages (
             session_id, chat_id, role, content, kind, tool_calls, tool_results,
             status, tokens_used, ctx_used, ctx_max, started_at, finished_at,
-            created_at
+            created_at, metadata
           )
           SELECT
             ${source.session_id}, ${chat!.id}, role, content, kind,
@@ -239,7 +239,8 @@ export function registerChatRoutes(
             tokens_used, ctx_used, ctx_max, started_at, finished_at,
             clock_timestamp() + (
               ROW_NUMBER() OVER (ORDER BY created_at ASC, id ASC) * INTERVAL '1 microsecond'
-            )
+            ),
+            metadata
           FROM messages
           WHERE chat_id = ${source.id}
             AND created_at <= ${target.created_at}::timestamptz
@@ -268,7 +269,7 @@ export function registerChatRoutes(
       }
       const rows = await sql<Message[]>`
         SELECT id, session_id, chat_id, role, content, kind, tool_calls, tool_results, status, last_seq,
-               tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at
+               tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at, metadata
         FROM messages
         WHERE chat_id = ${req.params.id}
         ORDER BY created_at ASC, id ASC

apps/server/src/routes/messages.ts

@@ -7,6 +7,13 @@ const SendBody = z.object({
   content: z.string().min(1).max(64_000),
 });
 
+// v1.8.2: Continue extends an inference loop that hit the tool budget. Caller
+// passes the sentinel message it's continuing from; server validates shape
+// and the per-chat hard ceiling before resuming.
+const ContinueBody = z.object({
+  sentinel_message_id: z.string().uuid(),
+});
+
 interface MessageHandlers {
   enqueueInference: (sessionId: string, chatId: string, assistantMessageId: string, user: string) => void;
   enqueueCompact: (sessionId: string, chatId: string, compactMessageId: string, user: string) => void;
@@ -36,7 +43,7 @@ export function registerMessageRoutes(
       }
       const rows = await sql<Message[]>`
         SELECT id, session_id, chat_id, role, content, kind, tool_calls, tool_results, status, last_seq,
-               tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at
+               tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at, metadata
         FROM messages
         WHERE session_id = ${req.params.id}
         ORDER BY created_at ASC, id ASC
@@ -253,6 +260,76 @@ export function registerMessageRoutes(
     }
   );
 
+  app.post<{ Params: { id: string } }>(
+    '/api/chats/:id/continue',
+    async (req, reply) => {
+      const parsed = ContinueBody.safeParse(req.body);
+      if (!parsed.success) {
+        reply.code(400);
+        return { error: 'invalid body', details: parsed.error.flatten() };
+      }
+
+      const chatRows = await sql<Chat[]>`
+        SELECT id, session_id FROM chats WHERE id = ${req.params.id} AND status = 'open'
+      `;
+      if (chatRows.length === 0) {
+        reply.code(404);
+        return { error: 'chat not found' };
+      }
+      const chat = chatRows[0]!;
+      const sessionId = chat.session_id;
+
+      // Cap-hit sentinels are only ever inserted after a turn completes, so
+      // there must not be an active inference at this moment. If there is,
+      // the client is racing the cap-hit summary that just emitted the
+      // sentinel — bail rather than enqueue a parallel run.
+      if (handlers.hasActiveInference(chat.id)) {
+        reply.code(409);
+        return { error: 'chat is currently streaming' };
+      }
+
+      const sentinel = await sql<{ metadata: { kind?: unknown; can_continue?: unknown } | null }[]>`
+        SELECT metadata
+        FROM messages
+        WHERE id = ${parsed.data.sentinel_message_id}
+          AND chat_id = ${chat.id}
+          AND role = 'system'
+      `;
+      if (sentinel.length === 0) {
+        reply.code(404);
+        return { error: 'sentinel not found' };
+      }
+      const meta = sentinel[0]!.metadata;
+      if (!meta || meta.kind !== 'cap_hit') {
+        reply.code(400);
+        return { error: 'message is not a cap-hit sentinel' };
+      }
+      // Server-side hard ceiling check. UI already disables the button when
+      // can_continue is false; defending against a stale tab or a direct
+      // API hit is the only reason this lives on the server too.
+      if (meta.can_continue !== true) {
+        reply.code(409);
+        return { error: 'hard limit reached for this chat' };
+      }
+
+      const result = await sql.begin(async (tx) => {
+        const [assistantMsg] = await tx<{ id: string }[]>`
+          INSERT INTO messages (session_id, chat_id, role, content, status, created_at)
+          VALUES (${sessionId}, ${chat.id}, 'assistant', '', 'streaming', clock_timestamp())
+          RETURNING id
+        `;
+        await tx`UPDATE sessions SET updated_at = clock_timestamp() WHERE id = ${sessionId}`;
+        await tx`UPDATE chats SET updated_at = clock_timestamp() WHERE id = ${chat.id}`;
+        return { assistant_message_id: assistantMsg!.id };
+      });
+
+      handlers.enqueueInference(sessionId, chat.id, result.assistant_message_id, 'default');
+
+      reply.code(202);
+      return result;
+    }
+  );
+
   app.post<{ Params: { id: string } }>(
     '/api/chats/:id/force_send',
     async (req, reply) => {

apps/server/src/routes/ws.ts

@@ -23,7 +23,7 @@ export function registerWebSocket(
 
       const messages = await sql<Message[]>`
         SELECT id, session_id, chat_id, role, content, kind, tool_calls, tool_results, status, last_seq,
-               tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at
+               tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at, metadata
         FROM messages
         WHERE session_id = ${sessionId}
         ORDER BY created_at ASC, id ASC

apps/server/src/schema.sql

@@ -158,3 +158,10 @@ END $$;
 -- the DB; they live in builtins (services/agents.ts) and a per-project AGENTS.md.
 -- agent_id is the slugified agent name. NULL means "use BooCode defaults".
 ALTER TABLE sessions ADD COLUMN IF NOT EXISTS agent_id TEXT;
+
+-- v1.8.2: per-message metadata for sentinels (cap-hit) and structured error
+-- reasons. JSONB so future kinds can extend without further schema churn.
+-- Shape for cap_hit:  { kind: 'cap_hit', used: number, limit: number,
+--                       agent_name: string|null, can_continue: boolean }
+-- Shape for errors:   { error_reason: 'llm_provider_error'|..., error_text: string }
+ALTER TABLE messages ADD COLUMN IF NOT EXISTS metadata JSONB;

apps/server/src/services/__tests__/inference.test.ts

@@ -21,6 +21,7 @@ function makeSession(overrides: Partial<Session> = {}): Session {
     status: 'open',
     created_at: new Date(0).toISOString(),
     updated_at: new Date(0).toISOString(),
+    agent_id: null,
     ...overrides,
   };
 }
@@ -62,6 +63,7 @@ function makeMessage(
     started_at: null,
     finished_at: null,
     created_at: new Date(counter * 1000).toISOString(),
+    metadata: null,
     ...overrides,
   };
 }

apps/server/src/services/agents.ts

@@ -29,6 +29,9 @@ interface ParsedFrontmatter {
   tools?: string[];
   description?: string;
   model?: string;
+  // v1.8.2: optional per-agent tool-loop budget. Absent → inference resolves
+  // from the agent's toolset at runtime.
+  max_tool_calls?: number;
 }
 
 function stripQuotes(s: string): string {
@@ -89,6 +92,21 @@ function parseFrontmatter(yaml: string): { data: ParsedFrontmatter; errors: stri
       data.description = stripQuotes(valueRaw);
     } else if (key === 'model') {
       data.model = stripQuotes(valueRaw);
+    } else if (key === 'max_tool_calls') {
+      // v1.8.2: 1..100 inclusive integer. Out-of-range values are skipped
+      // with a warning rather than throwing — agents shouldn't be unusable
+      // because of a typo on a defaulted field. Non-numeric or non-integer
+      // still hard-fails the block, matching `temperature` behavior.
+      const n = Number(valueRaw);
+      if (Number.isInteger(n) && n >= 1 && n <= 100) {
+        data.max_tool_calls = n;
+      } else if (Number.isInteger(n)) {
+        console.warn(
+          `agents: max_tool_calls ${n} out of range 1-100, ignoring (falling back to default)`,
+        );
+      } else {
+        errors.push(`max_tool_calls must be an integer 1-100 (got "${valueRaw}")`);
+      }
     }
     // Unknown keys silently ignored — forward-compat.
   }
@@ -177,6 +195,7 @@ function parseAgentSection(section: RawSection): Omit<Agent, 'source'> {
     temperature: typeof fm.temperature === 'number' ? fm.temperature : DEFAULT_TEMPERATURE,
     tools: filteredTools,
     model: typeof fm.model === 'string' && fm.model.length > 0 ? fm.model : null,
+    max_tool_calls: typeof fm.max_tool_calls === 'number' ? fm.max_tool_calls : null,
   };
 }
 

apps/server/src/services/inference.ts

@@ -1,8 +1,23 @@
 import type { FastifyBaseLogger } from 'fastify';
 import type { Sql } from '../db.js';
 import type { Config } from '../config.js';
-import type { Agent, Message, Project, Session, ToolCall, UserStreamFrame } from '../types/api.js';
-import { ALL_TOOLS, TOOLS_BY_NAME, toolJsonSchemas, type ToolJsonSchema } from './tools.js';
+import type {
+  Agent,
+  ErrorReason,
+  Message,
+  MessageMetadata,
+  Project,
+  Session,
+  ToolCall,
+  UserStreamFrame,
+} from '../types/api.js';
+import {
+  ALL_TOOLS,
+  READ_ONLY_TOOL_NAMES,
+  TOOLS_BY_NAME,
+  toolJsonSchemas,
+  type ToolJsonSchema,
+} from './tools.js';
 import { PathScopeError, resolveProjectRoot } from './path_guard.js';
 import { maybeAutoNameChat } from './auto_name.js';
 import { getAgentById } from './agents.js';
@@ -11,7 +26,39 @@ const BASE_SYSTEM_PROMPT = (projectPath: string) =>
   `You are BooCode Chat, a code investigation assistant. The user is working on a project located at ${projectPath}. Use the file-read tools (view_file, list_dir, grep, find_files) to investigate code when needed. Be concise. Cite file paths and line numbers when discussing code. Do not hallucinate file contents — read the file first. Tool results may be truncated; if so, narrow your query rather than guessing.`;
 
 const DB_FLUSH_INTERVAL_MS = 500;
-const MAX_TOOL_LOOP_DEPTH = 15;
+
+// v1.8.2: tool-call budget defaults. Resolved per-turn by resolveToolBudget.
+//   - Agent with explicit max_tool_calls: that value.
+//   - Agent with read-only-only tools:    BUDGET_READ_ONLY (30).
+//   - Agent with any non-read-only tool:  BUDGET_NON_READ_ONLY (10).
+//   - No agent (raw chat):                BUDGET_NO_AGENT (15).
+const BUDGET_READ_ONLY = 30;
+const BUDGET_NON_READ_ONLY = 10;
+const BUDGET_NO_AGENT = 15;
+
+const READ_ONLY_SET: ReadonlySet<string> = new Set(READ_ONLY_TOOL_NAMES);
+
+function resolveToolBudget(agent: Agent | null): number {
+  if (agent?.max_tool_calls != null) return agent.max_tool_calls;
+  if (!agent) return BUDGET_NO_AGENT;
+  const allReadOnly = agent.tools.every((t) => READ_ONLY_SET.has(t));
+  return allReadOnly ? BUDGET_READ_ONLY : BUDGET_NON_READ_ONLY;
+}
+
+// Synthetic system note appended to the cap-hit summary call. Verbatim from
+// the v1.8.2 spec — do not paraphrase: the model is more reliable when the
+// instruction is short, declarative, and identical across calls.
+const CAP_HIT_SUMMARY_NOTE = (limit: number) =>
+  `You've reached the tool budget (${limit} calls). Produce the best answer you can with what you have. Do not call more tools.`;
+
+function isCapHitSentinel(m: Message): boolean {
+  return (
+    m.role === 'system' &&
+    m.metadata !== null &&
+    typeof m.metadata === 'object' &&
+    (m.metadata as { kind?: unknown }).kind === 'cap_hit'
+  );
+}
 
 export interface InferenceFrame {
   type:
@@ -29,12 +76,22 @@ export interface InferenceFrame {
   chat_id?: string;
   tool_message_id?: string;
   tool_call_id?: string;
-  role?: 'assistant' | 'tool' | 'user';
+  // v1.8.2: 'system' added so cap-hit sentinel messages can announce themselves
+  // through the normal message_started → delta → message_complete sequence.
+  role?: 'assistant' | 'tool' | 'user' | 'system';
   content?: string;
   tool_call?: ToolCall;
   output?: unknown;
   truncated?: boolean;
   error?: string;
+  // v1.8.2: structured error reason. Set on `type: 'error'` so the UI can
+  // surface a specific message; `error` stays the human-readable text.
+  reason?: ErrorReason;
+  // v1.8.2: piggybacks on `message_complete` so static or terminally-resolved
+  // messages can carry their persisted metadata to the live stream without a
+  // refetch (sentinels carry { kind: 'cap_hit', ... }; failed messages carry
+  // { kind: 'error', ... }).
+  metadata?: MessageMetadata | null;
   tokens_used?: number | null;
   ctx_used?: number | null;
   ctx_max?: number | null;
@@ -135,6 +192,11 @@ export function buildMessagesPayload(
       out.push({ role: 'system', content: m.content });
       continue;
     }
+    // v1.8.2: cap-hit sentinels are UI-only — never send them to the LLM. The
+    // synthetic "you've reached the tool budget" note lives only inside the
+    // summary call's messages array and is never persisted, so on Continue
+    // the model resumes with a clean context.
+    if (isCapHitSentinel(m)) continue;
     if (m.role === 'assistant' && m.status === 'streaming') continue;
     if (m.role === 'assistant' && m.status === 'cancelled') continue;
     if (m.role === 'tool') {
@@ -193,7 +255,7 @@ async function loadContext(
 
   const history = await sql<Message[]>`
     SELECT id, session_id, chat_id, role, content, kind, tool_calls, tool_results, status, last_seq,
-           tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at
+           tokens_used, ctx_used, ctx_max, started_at, finished_at, created_at, metadata
     FROM messages
     WHERE chat_id = ${chatId}
     ORDER BY created_at ASC, id ASC
@@ -379,7 +441,10 @@ interface TurnArgs {
   sessionId: string;
   chatId: string;
   assistantMessageId: string;
-  depth: number;
+  // v1.8.2: cumulative tool calls executed this run. Compared against the
+  // resolved budget at the top of each turn. Replaces the older `depth`
+  // counter (which counted iterations, not invocations).
+  toolsUsed: number;
   signal: AbortSignal | undefined;
 }
 
@@ -480,13 +545,32 @@ async function handleAbortOrError(
   const { sessionId, chatId, assistantMessageId } = args;
   const isAbort = err instanceof Error && err.name === 'AbortError';
   const finalStatus = isAbort ? 'cancelled' : 'failed';
-  await ctx.sql`
-    UPDATE messages
-    SET status = ${finalStatus},
-        content = ${accumulated},
-        finished_at = clock_timestamp()
-    WHERE id = ${assistantMessageId}
-  `;
+  const errMsg = err instanceof Error ? err.message : String(err);
+  // v1.8.2: persist a structured error metadata blob on genuine failures so
+  // the bubble can render the reason on reload without re-deriving from the
+  // (one-shot) WS error frame. User-initiated abort skips this — there's no
+  // "reason" to surface for a stop the user already explicitly chose.
+  const errorMetadata: MessageMetadata | null = isAbort
+    ? null
+    : { kind: 'error', error_reason: 'llm_provider_error', error_text: errMsg };
+  if (errorMetadata) {
+    await ctx.sql`
+      UPDATE messages
+      SET status = ${finalStatus},
+          content = ${accumulated},
+          finished_at = clock_timestamp(),
+          metadata = ${ctx.sql.json(errorMetadata as never)}
+      WHERE id = ${assistantMessageId}
+    `;
+  } else {
+    await ctx.sql`
+      UPDATE messages
+      SET status = ${finalStatus},
+          content = ${accumulated},
+          finished_at = clock_timestamp()
+      WHERE id = ${assistantMessageId}
+    `;
+  }
   const [failSessRow] = await ctx.sql<{ project_id: string; name: string; updated_at: string }[]>`
     UPDATE sessions SET updated_at = clock_timestamp()
     WHERE id = ${sessionId}
@@ -494,9 +578,10 @@ async function handleAbortOrError(
   `;
   ctx.publishUser({ type: 'session_updated', session_id: sessionId, project_id: failSessRow!.project_id, name: failSessRow!.name, updated_at: failSessRow!.updated_at });
   // v1.8 mobile-tabs: cancellation is a user-initiated stop, treat as idle;
-  // genuine errors flip the dot red.
-  ctx.publishUser({ type: 'chat_status', chat_id: chatId, status: isAbort ? 'idle' : 'error', at: new Date().toISOString() });
+  // genuine errors flip the dot red. v1.8.2: error path also carries a
+  // machine-readable `reason` so the UI can render specifics inline.
   if (isAbort) {
+    ctx.publishUser({ type: 'chat_status', chat_id: chatId, status: 'idle', at: new Date().toISOString() });
     ctx.publish(sessionId, {
       type: 'message_complete',
       message_id: assistantMessageId,
@@ -504,12 +589,19 @@ async function handleAbortOrError(
     });
     ctx.log.info({ sessionId, chatId, assistantMessageId }, 'inference cancelled');
   } else {
-    const errMsg = err instanceof Error ? err.message : String(err);
+    ctx.publishUser({
+      type: 'chat_status',
+      chat_id: chatId,
+      status: 'error',
+      at: new Date().toISOString(),
+      reason: 'llm_provider_error',
+    });
     ctx.publish(sessionId, {
       type: 'error',
       message_id: assistantMessageId,
       chat_id: chatId,
       error: errMsg,
+      reason: 'llm_provider_error',
     });
     ctx.log.error({ err, sessionId, assistantMessageId }, 'inference failed');
   }
@@ -523,7 +615,7 @@ async function executeToolPhase(
   session: Session,
   projectRoot: string
 ): Promise<void> {
-  const { sessionId, chatId, assistantMessageId, depth, signal } = args;
+  const { sessionId, chatId, assistantMessageId, toolsUsed, signal } = args;
   const { content, toolCalls, promptTokens, completionTokens, nCtx } = result;
 
   const [updated] = await ctx.sql<
@@ -607,7 +699,10 @@ async function executeToolPhase(
     sessionId,
     chatId,
     assistantMessageId: nextAssistant!.id,
-    depth: depth + 1,
+    // v1.8.2: charge this turn's actual tool invocations against the budget.
+    // One assistant message can emit multiple tool_calls, so we add the run
+    // count, not 1. The next turn's budget check sees the cumulative total.
+    toolsUsed: toolsUsed + result.toolCalls.length,
     signal,
   });
 }
@@ -671,25 +766,7 @@ async function runAssistantTurn(
   ctx: InferenceContext,
   args: TurnArgs,
 ): Promise<void> {
-  const { sessionId, chatId, assistantMessageId, depth } = args;
-
-  if (depth > MAX_TOOL_LOOP_DEPTH) {
-    await ctx.sql`
-      UPDATE messages
-      SET status = 'failed',
-          content = ${'tool loop depth exceeded'},
-          finished_at = clock_timestamp()
-      WHERE id = ${assistantMessageId}
-    `;
-    ctx.publish(sessionId, {
-      type: 'error',
-      message_id: assistantMessageId,
-      chat_id: chatId,
-      error: 'tool loop depth exceeded',
-    });
-    ctx.publishUser({ type: 'chat_status', chat_id: chatId, status: 'error', at: new Date().toISOString() });
-    return;
-  }
+  const { sessionId, chatId } = args;
 
   const loaded = await loadContext(ctx.sql, sessionId, chatId);
   if (!loaded) {
@@ -704,6 +781,17 @@ async function runAssistantTurn(
   const agent = session.agent_id
     ? await getAgentById(project.path, session.agent_id)
     : null;
+
+  // v1.8.2: cap-hit replaces the older "tool loop depth exceeded" failure.
+  // When we've already burned the budget *before* this turn even runs, we
+  // skip straight to the summary flow — the in-flight assistant message slot
+  // gets reused for the wrap-up reply instead of being marked failed.
+  const budget = resolveToolBudget(agent);
+  if (args.toolsUsed >= budget) {
+    await runCapHitSummary(ctx, args, session, project, history, agent, budget);
+    return;
+  }
+
   const messages = buildMessagesPayload(session, project, history, agent);
 
   const state: StreamPhaseState = { accumulated: '', startedAt: null };
@@ -730,7 +818,264 @@ export async function runInference(
   assistantMessageId: string,
   signal?: AbortSignal
 ): Promise<void> {
-  return runAssistantTurn(ctx, { sessionId, chatId, assistantMessageId, depth: 0, signal });
+  // v1.8.2: every fresh inference (initial send, regenerate, force_send,
+  // continue) starts with a clean budget. Tool-call accumulation across
+  // Continue invocations is what the hard ceiling guards against, not the
+  // per-call budget.
+  return runAssistantTurn(ctx, { sessionId, chatId, assistantMessageId, toolsUsed: 0, signal });
+}
+
+// v1.8.2: cap-hit summary flow. Called instead of erroring when the loop
+// hits its budget. Reuses the in-flight assistant message slot to stream a
+// short wrap-up reply with the synthetic note prepended and tools disabled,
+// then always inserts a cap_hit sentinel afterward (regardless of summary
+// outcome) so the UI can show a Continue affordance.
+async function runCapHitSummary(
+  ctx: InferenceContext,
+  args: TurnArgs,
+  session: Session,
+  project: Project,
+  history: Message[],
+  agent: Agent | null,
+  budget: number,
+): Promise<void> {
+  const { sessionId, chatId, assistantMessageId, signal } = args;
+
+  const messages = buildMessagesPayload(session, project, history, agent);
+  messages.push({ role: 'system', content: CAP_HIT_SUMMARY_NOTE(budget) });
+
+  const startedRow = await ctx.sql<{ started_at: string }[]>`
+    UPDATE messages
+    SET started_at = clock_timestamp()
+    WHERE id = ${assistantMessageId}
+    RETURNING started_at
+  `;
+  const startedAt = startedRow[0]?.started_at ?? null;
+
+  ctx.publish(sessionId, {
+    type: 'message_started',
+    message_id: assistantMessageId,
+    chat_id: chatId,
+    role: 'assistant',
+  });
+
+  let accumulated = '';
+  let pendingFlushTimer: NodeJS.Timeout | null = null;
+  let flushPromise: Promise<unknown> = Promise.resolve();
+  const flushNow = () => {
+    if (pendingFlushTimer) {
+      clearTimeout(pendingFlushTimer);
+      pendingFlushTimer = null;
+    }
+    const snapshot = accumulated;
+    flushPromise = flushPromise.then(() =>
+      ctx.sql`UPDATE messages SET content = ${snapshot} WHERE id = ${assistantMessageId}`
+    );
+  };
+  const scheduleFlush = () => {
+    if (pendingFlushTimer) return;
+    pendingFlushTimer = setTimeout(() => {
+      pendingFlushTimer = null;
+      flushNow();
+    }, DB_FLUSH_INTERVAL_MS);
+  };
+
+  let summaryOk = false;
+  let summarySoftCancelled = false;
+  let summaryError: string | null = null;
+  let result: StreamResult | null = null;
+  try {
+    result = await streamCompletion(
+      ctx,
+      session.model,
+      messages,
+      { tools: null, temperature: agent?.temperature },
+      (delta) => {
+        accumulated += delta;
+        ctx.publish(sessionId, {
+          type: 'delta',
+          message_id: assistantMessageId,
+          chat_id: chatId,
+          content: delta,
+        });
+        scheduleFlush();
+      },
+      signal,
+    );
+    summaryOk = true;
+  } catch (err) {
+    if (err instanceof Error && err.name === 'AbortError') {
+      summarySoftCancelled = true;
+    } else {
+      summaryError = err instanceof Error ? err.message : String(err);
+    }
+  } finally {
+    if (pendingFlushTimer) {
+      clearTimeout(pendingFlushTimer);
+      pendingFlushTimer = null;
+    }
+    await flushPromise;
+  }
+
+  // Finalize the summary message based on the three outcomes. The sentinel
+  // is inserted regardless so the user always has the Continue affordance —
+  // even on a partial / failed summary the chat history shows where the
+  // budget was hit.
+  if (summaryOk && result) {
+    const [updated] = await ctx.sql<
+      { tokens_used: number | null; ctx_used: number | null; ctx_max: number | null; finished_at: string | null }[]
+    >`
+      UPDATE messages
+      SET content = ${result.content},
+          status = 'complete',
+          tokens_used = ${result.completionTokens},
+          ctx_used = ${result.promptTokens},
+          ctx_max = ${result.nCtx},
+          finished_at = clock_timestamp()
+      WHERE id = ${assistantMessageId}
+      RETURNING tokens_used, ctx_used, ctx_max, finished_at
+    `;
+    ctx.publish(sessionId, {
+      type: 'message_complete',
+      message_id: assistantMessageId,
+      chat_id: chatId,
+      tokens_used: updated?.tokens_used ?? null,
+      ctx_used: updated?.ctx_used ?? null,
+      ctx_max: updated?.ctx_max ?? null,
+      started_at: startedAt,
+      finished_at: updated?.finished_at ?? null,
+      model: session.model,
+    });
+  } else if (summarySoftCancelled) {
+    await ctx.sql`
+      UPDATE messages
+      SET content = ${accumulated},
+          status = 'cancelled',
+          finished_at = clock_timestamp()
+      WHERE id = ${assistantMessageId}
+    `;
+    ctx.publish(sessionId, {
+      type: 'message_complete',
+      message_id: assistantMessageId,
+      chat_id: chatId,
+    });
+  } else {
+    const errMeta: MessageMetadata = {
+      kind: 'error',
+      error_reason: 'summary_after_cap_failed',
+      error_text: summaryError ?? 'summary failed',
+    };
+    await ctx.sql`
+      UPDATE messages
+      SET content = ${accumulated},
+          status = 'failed',
+          finished_at = clock_timestamp(),
+          metadata = ${ctx.sql.json(errMeta as never)}
+      WHERE id = ${assistantMessageId}
+    `;
+    ctx.publish(sessionId, {
+      type: 'error',
+      message_id: assistantMessageId,
+      chat_id: chatId,
+      error: summaryError ?? 'summary failed',
+      reason: 'summary_after_cap_failed',
+    });
+  }
+
+  // Bump session/chat updated_at exactly once for this turn.
+  const [sessRow] = await ctx.sql<{ project_id: string; name: string; updated_at: string }[]>`
+    UPDATE sessions SET updated_at = clock_timestamp()
+    WHERE id = ${sessionId}
+    RETURNING project_id, name, updated_at
+  `;
+  ctx.publishUser({
+    type: 'session_updated',
+    session_id: sessionId,
+    project_id: sessRow!.project_id,
+    name: sessRow!.name,
+    updated_at: sessRow!.updated_at,
+  });
+
+  await insertCapHitSentinel(ctx, sessionId, chatId, agent, budget);
+
+  // Status frame fires last so the dot color reflects the terminal state.
+  // Success → idle, abort → idle (user-driven stop), error → error+reason.
+  if (summaryOk) {
+    ctx.publishUser({ type: 'chat_status', chat_id: chatId, status: 'idle', at: new Date().toISOString() });
+  } else if (summarySoftCancelled) {
+    ctx.publishUser({ type: 'chat_status', chat_id: chatId, status: 'idle', at: new Date().toISOString() });
+  } else {
+    ctx.publishUser({
+      type: 'chat_status',
+      chat_id: chatId,
+      status: 'error',
+      at: new Date().toISOString(),
+      reason: 'summary_after_cap_failed',
+    });
+  }
+
+  ctx.log.info(
+    { sessionId, chatId, assistantMessageId, budget, summaryOk, summaryCancelled: summarySoftCancelled },
+    'inference cap-hit summary finished',
+  );
+}
+
+async function insertCapHitSentinel(
+  ctx: InferenceContext,
+  sessionId: string,
+  chatId: string,
+  agent: Agent | null,
+  budget: number,
+): Promise<void> {
+  // Hard ceiling: count prior cap_hit sentinels in this chat. After two
+  // continues (sentinel count of 2), the next sentinel reports can_continue
+  // false and the UI disables the Continue button.
+  const priorRows = await ctx.sql<{ count: number }[]>`
+    SELECT COUNT(*)::int AS count
+    FROM messages
+    WHERE chat_id = ${chatId}
+      AND role = 'system'
+      AND metadata->>'kind' = 'cap_hit'
+  `;
+  const priorCount = priorRows[0]?.count ?? 0;
+  const canContinue = priorCount < 2;
+  const metadata: MessageMetadata = {
+    kind: 'cap_hit',
+    used: budget,
+    limit: budget,
+    agent_name: agent?.name ?? null,
+    can_continue: canContinue,
+  };
+  const content = `Reached tool budget (${budget}/${budget}). Continue to extend.`;
+
+  const [row] = await ctx.sql<{ id: string }[]>`
+    INSERT INTO messages (session_id, chat_id, role, content, status, created_at, metadata)
+    VALUES (${sessionId}, ${chatId}, 'system', ${content}, 'complete', clock_timestamp(), ${ctx.sql.json(metadata as never)})
+    RETURNING id
+  `;
+
+  // The sentinel content is static, but we still walk the standard frame
+  // sequence (started → delta → complete) so useSessionStream's reducer
+  // appends it via the same path it uses for streaming assistant messages.
+  // The delta carries the full text in one chunk.
+  ctx.publish(sessionId, {
+    type: 'message_started',
+    message_id: row!.id,
+    chat_id: chatId,
+    role: 'system',
+  });
+  ctx.publish(sessionId, {
+    type: 'delta',
+    message_id: row!.id,
+    chat_id: chatId,
+    content,
+  });
+  ctx.publish(sessionId, {
+    type: 'message_complete',
+    message_id: row!.id,
+    chat_id: chatId,
+    metadata,
+  });
 }
 
 const COMPACT_SYSTEM_PROMPT =

apps/server/src/services/tools.ts

@@ -308,6 +308,19 @@ export const ALL_TOOLS: ReadonlyArray<ToolDef<unknown>> = [
   gitStatus as ToolDef<unknown>,
 ];
 
+// v1.8.2: forward-compatible read-only whitelist. An agent whose `tools` is
+// fully contained in this set gets a generous default tool budget (30);
+// anything outside means the agent can mutate state and gets a tighter
+// default (10). Every tool in v1.8.2 happens to be read-only, so the
+// non-RO branch only takes effect once BooCoder lands write tools.
+export const READ_ONLY_TOOL_NAMES = [
+  'view_file',
+  'list_dir',
+  'grep',
+  'find_files',
+  'git_status',
+] as const;
+
 export const TOOLS_BY_NAME: Record<string, ToolDef<unknown>> = Object.fromEntries(
   ALL_TOOLS.map((t) => [t.name, t])
 );

apps/server/src/types/api.ts

@@ -45,6 +45,10 @@ export interface Agent {
   tools: string[];       // whitelist of tool names; empty = no tools allowed
   model: string | null;  // null means "session.model wins"
   source: AgentSource;
+  // v1.8.2: per-agent tool-loop budget. null means resolve at runtime from the
+  // agent's toolset (30 if all tools are read-only, 10 otherwise) or 15 for
+  // raw chat with no agent.
+  max_tool_calls: number | null;
 }
 
 // One entry per malformed `## Name` block. Per-block errors don't fail the
@@ -100,6 +104,31 @@ export interface ToolResult {
   error?: string;
 }
 
+// v1.8.2: structured reason codes for failed inferences. `error` carries the
+// human text; `reason` is the machine-readable discriminator the UI matches
+// on (with `error` as fallback when reason is absent or unrecognized).
+export type ErrorReason =
+  | 'llm_provider_error'
+  | 'tool_execution_failed'
+  | 'summary_after_cap_failed';
+
+// v1.8.2: shapes stored in messages.metadata. Discriminated on `kind`.
+//   cap_hit  — system sentinel emitted when tool budget is exhausted
+//   error    — attached to a failed assistant message so UI can show reason
+export type MessageMetadata =
+  | {
+      kind: 'cap_hit';
+      used: number;
+      limit: number;
+      agent_name: string | null;
+      can_continue: boolean;
+    }
+  | {
+      kind: 'error';
+      error_reason: ErrorReason;
+      error_text: string;
+    };
+
 export interface Message {
   id: string;
   session_id: string;
@@ -117,6 +146,9 @@ export interface Message {
   started_at: string | null;
   finished_at: string | null;
   created_at: string;
+  // v1.8.2: per-message metadata. See MessageMetadata for the discriminated
+  // shapes currently in use.
+  metadata: MessageMetadata | null;
 }
 
 export interface ModelInfo {
@@ -257,11 +289,14 @@ export interface ProjectUpdatedFrame {
 }
 // v1.8 mobile-tabs: server can't know about client-side panes, so status
 // is keyed by chat_id. Frontend dot derives pane status from pane.activeChatId.
+// v1.8.2: optional `reason` carries a machine-readable code when status is
+// 'error'. UI prefers reason; falls back to no detail when absent.
 export interface ChatStatusFrame {
   type: 'chat_status';
   chat_id: string;
   status: 'working' | 'idle' | 'error';
   at: string;
+  reason?: ErrorReason;
 }
 export type UserStreamFrame =
   | ProjectCreatedFrame

apps/web/src/api/client.ts

@@ -152,6 +152,13 @@ export const api = {
         `/api/chats/${chatId}/force_send`,
         { method: 'POST', body: JSON.stringify({ content }) }
       ),
+    // v1.8.2: extend an inference that hit the tool budget. `sentinelMessageId`
+    // is the cap-hit sentinel message the user clicked Continue on.
+    continue: (chatId: string, sentinelMessageId: string) =>
+      request<{ assistant_message_id: string }>(
+        `/api/chats/${chatId}/continue`,
+        { method: 'POST', body: JSON.stringify({ sentinel_message_id: sentinelMessageId }) }
+      ),
     fork: (chatId: string, body: { messageId: string; name?: string }) =>
       request<Chat>(`/api/chats/${chatId}/fork`, {
         method: 'POST',

apps/web/src/api/types.ts

@@ -44,6 +44,10 @@ export interface Agent {
   tools: string[];
   model: string | null;
   source: AgentSource;
+  // v1.8.2: per-agent tool-loop budget. null means resolve at runtime from
+  // the agent's toolset (30 for all read-only, 10 otherwise) or 15 for raw
+  // chat with no agent.
+  max_tool_calls: number | null;
 }
 
 export interface AgentParseError {
@@ -89,6 +93,32 @@ export interface ToolResult {
   error?: string;
 }
 
+// v1.8.2: structured reason codes that flow through error frames / metadata.
+// `error` text stays human; `reason` is the discriminator the UI matches on.
+export type ErrorReason =
+  | 'llm_provider_error'
+  | 'tool_execution_failed'
+  | 'summary_after_cap_failed';
+
+// v1.8.2: shapes stored in Message.metadata. Discriminated on `kind`.
+//   cap_hit — sentinel emitted when the tool budget is hit; carries the
+//             budget + agent name + whether Continue is still allowed.
+//   error   — attached to a failed assistant message so the bubble can show
+//             a specific reason on reload (WS error frame is one-shot).
+export type MessageMetadata =
+  | {
+      kind: 'cap_hit';
+      used: number;
+      limit: number;
+      agent_name: string | null;
+      can_continue: boolean;
+    }
+  | {
+      kind: 'error';
+      error_reason: ErrorReason;
+      error_text: string;
+    };
+
 export interface Message {
   id: string;
   session_id: string;
@@ -106,6 +136,9 @@ export interface Message {
   started_at: string | null;
   finished_at: string | null;
   created_at: string;
+  // v1.8.2: per-message metadata; see MessageMetadata. null for the vast
+  // majority of messages.
+  metadata: MessageMetadata | null;
 }
 
 export interface ModelInfo {
@@ -225,7 +258,13 @@ export type WsFrame =
       ctx_max?: number | null;
       started_at?: string | null;
       finished_at?: string | null;
+      // v1.8.2: piggybacks the persisted metadata onto the terminal frame so
+      // cap-hit sentinels (and any future stamped-on-complete metadata) flow
+      // to the client without a refetch.
+      metadata?: MessageMetadata | null;
     }
   | { type: 'messages_deleted'; message_ids: string[]; chat_id?: string }
   | { type: 'chat_renamed'; chat_id: string; name: string }
-  | { type: 'error'; message_id?: string; chat_id?: string; error: string };
+  // v1.8.2: `reason` discriminates structured failures (the UI prefers it
+  // over `error` text when present).
+  | { type: 'error'; message_id?: string; chat_id?: string; error: string; reason?: ErrorReason };

apps/web/src/components/CapHitSentinel.tsx

@@ -0,0 +1,90 @@
+import { useState } from 'react';
+import { AlertCircle } from 'lucide-react';
+import { toast } from 'sonner';
+import { api } from '@/api/client';
+import type { Message } from '@/api/types';
+import { Button } from '@/components/ui/button';
+
+interface Props {
+  message: Message;
+  // 1-indexed position among cap-hit sentinels in this chat. The first
+  // cap-hit is 1, second is 2, third is 3 (hard ceiling).
+  capHitPosition: number;
+  // Only the most recent sentinel shows the Continue button. Older ones
+  // render text-only — they've already been continued past.
+  isLatest: boolean;
+}
+
+// Hard ceiling = 3 cap-hits per chat ⇒ 2 continues max. Lives here in sync
+// with insertCapHitSentinel's `canContinue = priorCount < 2` rule in
+// services/inference.ts.
+const MAX_CONTINUES = 2;
+
+export function CapHitSentinel({ message, capHitPosition, isLatest }: Props) {
+  const meta = message.metadata;
+  // Defensive parse — if the row is somehow missing metadata we still render
+  // the bare text rather than crashing the chat.
+  const isCapHit =
+    meta !== null && typeof meta === 'object' && meta.kind === 'cap_hit';
+
+  const limit = isCapHit ? meta.limit : null;
+  const canContinue = isCapHit ? meta.can_continue : false;
+  const agentName = isCapHit ? meta.agent_name : null;
+  // `capHitPosition` is 1-indexed; `MAX_CONTINUES - (position - 1)` is the
+  // number of continues remaining including this one. Clamped to ≥0.
+  const remaining = Math.max(0, MAX_CONTINUES - (capHitPosition - 1));
+
+  const [continuing, setContinuing] = useState(false);
+
+  async function handleContinue() {
+    if (continuing || !canContinue || !isLatest) return;
+    setContinuing(true);
+    try {
+      await api.chats.continue(message.chat_id, message.id);
+    } catch (err) {
+      toast.error(err instanceof Error ? err.message : 'continue failed');
+    } finally {
+      setContinuing(false);
+    }
+  }
+
+  // Tooltip wording from the v1.8.2 spec. Disabled state takes precedence —
+  // the spec text "Hard limit reached — start a new chat" matches what the
+  // server returns when canContinue is false.
+  const enabledTooltip = limit
+    ? `Resumes with a fresh budget of ${limit} tool calls. ${remaining} continue${remaining === 1 ? '' : 's'} remaining on this chat.`
+    : undefined;
+  const disabledTooltip = 'Hard limit reached — start a new chat';
+
+  return (
+    <div className="rounded-md border border-amber-500/40 bg-amber-500/10 text-sm">
+      <div className="px-3 py-2 flex items-start gap-2">
+        <AlertCircle className="size-4 text-amber-500 shrink-0 mt-0.5" />
+        <div className="flex-1 min-w-0 space-y-1">
+          <div className="text-xs font-medium text-amber-700 dark:text-amber-300">
+            {isCapHit && limit !== null
+              ? `Reached tool budget (${limit}/${limit})${agentName ? ` — ${agentName}` : ''}.`
+              : 'Reached tool budget.'}
+          </div>
+          <div className="text-xs text-muted-foreground">
+            {message.content}
+          </div>
+          {isLatest && (
+            <div className="pt-1">
+              <Button
+                type="button"
+                size="sm"
+                variant="outline"
+                onClick={() => void handleContinue()}
+                disabled={!canContinue || continuing}
+                title={canContinue ? enabledTooltip : disabledTooltip}
+              >
+                {continuing ? 'Continuing…' : 'Continue'}
+              </Button>
+            </div>
+          )}
+        </div>
+      </div>
+    </div>
+  );
+}

apps/web/src/components/MessageBubble.tsx

@@ -4,10 +4,10 @@ import Markdown from 'react-markdown';
 import remarkGfm from 'remark-gfm';
 import { ChevronDown, ChevronRight, Copy, RefreshCw, Check, Share2, RotateCw, GitFork, Trash2 } from 'lucide-react';
 import { toast } from 'sonner';
-import type { Chat, Message } from '@/api/types';
+import type { Chat, ErrorReason, Message } from '@/api/types';
 import { api } from '@/api/client';
 import { sessionEvents } from '@/hooks/sessionEvents';
-import { ToolCallCard } from './ToolCallCard';
+import { CapHitSentinel } from './CapHitSentinel';
 import { CodeBlock } from './CodeBlock';
 import { Button } from '@/components/ui/button';
 import {
@@ -19,6 +19,15 @@ import {
   DialogTitle,
 } from '@/components/ui/dialog';
 
+// v1.8.2: human labels for the machine-readable error reasons that ride on
+// failed assistant messages via metadata.kind === 'error'. Kept short so the
+// inline render under "message failed" stays a single muted line.
+const ERROR_REASON_LABELS: Record<ErrorReason, string> = {
+  llm_provider_error: 'LLM provider error',
+  tool_execution_failed: 'Tool execution failed',
+  summary_after_cap_failed: 'Summary after tool budget hit failed',
+};
+
 // Match path-shaped substrings ending in `.ext`. Additionally require a `/`
 // in the match to reduce false positives in prose (e.g. plain `foo.ts` won't
 // match, but `src/foo.ts` will). False positives at the edges are accepted
@@ -94,6 +103,9 @@ function linkifyChildren(children: ReactNode, keyPrefix = 'l'): ReactNode {
 interface Props {
   message: Message;
   sessionChats?: Chat[];
+  // v1.8.2: passed by MessageList's render-item pass for cap-hit sentinels.
+  // Only the most recent sentinel shows the Continue button.
+  capHitInfo?: { position: number; isLatest: boolean };
 }
 
 function MarkdownBody({ content }: { content: string }) {
@@ -464,15 +476,34 @@ function CompactCard({ message, sessionChats }: { message: Message; sessionChats
   );
 }
 
-export function MessageBubble({ message, sessionChats }: Props) {
+export function MessageBubble({ message, sessionChats, capHitInfo }: Props) {
   if (message.kind === 'compact') {
     return <CompactCard message={message} sessionChats={sessionChats} />;
   }
 
-  if (message.role === 'tool') {
-    return <ToolCallCard message={message} />;
+  // v1.8.2: cap-hit sentinels render as a distinct system bubble with a
+  // Continue button. MessageList's pre-render pass tags each sentinel with
+  // its position; only the latest gets the actionable button.
+  if (
+    message.role === 'system' &&
+    message.metadata?.kind === 'cap_hit' &&
+    capHitInfo
+  ) {
+    return (
+      <CapHitSentinel
+        message={message}
+        capHitPosition={capHitInfo.position}
+        isLatest={capHitInfo.isLatest}
+      />
+    );
   }
 
+  // v1.8.2: tool messages and assistant tool_calls are now rendered by
+  // MessageList via ToolCallLine / ToolCallGroup. Tool-role messages reach
+  // this point only if MessageList didn't consume them (shouldn't happen,
+  // but guard against it by rendering nothing rather than a stale card).
+  if (message.role === 'tool') return null;
+
   if (message.role === 'user') {
     return (
       <div className="group flex flex-col items-end gap-1">
@@ -487,14 +518,17 @@ export function MessageBubble({ message, sessionChats }: Props) {
   const isStreaming = message.status === 'streaming';
   const failed = message.status === 'failed';
   const hasContent = message.content.length > 0;
-  const hasToolCalls = (message.tool_calls?.length ?? 0) > 0;
+  // v1.8.2: if metadata stamps an error reason, surface it inline under the
+  // generic "message failed" line. Keeps the user's eye where it already is
+  // rather than introducing a separate banner.
+  const errorMeta =
+    message.metadata !== null && message.metadata.kind === 'error'
+      ? message.metadata
+      : null;
 
   return (
     <div className="group flex flex-col gap-2">
-      {message.tool_calls?.map((tc) => (
-        <ToolCallCard key={tc.id} toolCall={tc} />
-      ))}
-      {(hasContent || (!hasToolCalls && isStreaming)) && (
+      {(hasContent || isStreaming) && (
         <div className="max-w-[90%] text-sm leading-relaxed space-y-2 break-words min-w-0">
           {hasContent ? <MarkdownBody content={message.content} /> : null}
           {isStreaming && (
@@ -503,12 +537,18 @@ export function MessageBubble({ message, sessionChats }: Props) {
         </div>
       )}
       {failed && (
-        <div className="text-xs text-destructive">message failed</div>
+        <div className="text-xs text-destructive">
+          message failed
+          {errorMeta && (
+            <span className="block text-muted-foreground mt-0.5">
+              {ERROR_REASON_LABELS[errorMeta.error_reason]}
+              {errorMeta.error_text ? ` — ${errorMeta.error_text}` : ''}
+            </span>
+          )}
+        </div>
       )}
       {!isStreaming && <StatsLine message={message} />}
-      {!isStreaming && (hasContent || hasToolCalls) && (
-        <ActionRow message={message} />
-      )}
+      {!isStreaming && hasContent && <ActionRow message={message} />}
     </div>
   );
 }

apps/web/src/components/MessageList.tsx

@@ -1,15 +1,128 @@
-import { useEffect, useRef } from 'react';
+import { useEffect, useMemo, useRef } from 'react';
 import type { Chat, Message } from '@/api/types';
 import { MessageBubble } from './MessageBubble';
+import { ToolCallGroup } from './ToolCallGroup';
+import { ToolCallLine, type ToolRun } from './ToolCallLine';
 
 interface Props {
   messages: Message[];
   sessionChats?: Chat[];
 }
 
+// v1.8.2: pre-render units. The single linear `messages` array gets walked
+// into a render-time list where each tool_call is a first-class item and
+// tool_result messages are folded onto their matching tool_run by id.
+type RenderItem =
+  | { kind: 'message'; message: Message; capHitInfo?: { position: number; isLatest: boolean } }
+  | { kind: 'tool_run'; run: ToolRun; key: string }
+  | { kind: 'tool_group'; runs: ToolRun[]; key: string };
+
+const GROUP_THRESHOLD = 3;
+
+function isCapHitSentinel(m: Message): boolean {
+  return m.role === 'system' && m.metadata?.kind === 'cap_hit';
+}
+
+// First pass: walk messages chronologically, expanding assistant tool_calls
+// into per-call run items and folding tool_result messages onto their
+// matching runs. Tool messages themselves never produce a render item.
+// Assistant messages produce a text render item only when they have text;
+// pure tool-call messages are "transparent" so consecutive tool runs can
+// still group across them.
+function flatten(messages: Message[]): RenderItem[] {
+  const items: RenderItem[] = [];
+  const runsByCallId = new Map<string, ToolRun>();
+
+  for (const m of messages) {
+    if (m.role === 'tool') {
+      if (m.tool_results) {
+        const run = runsByCallId.get(m.tool_results.tool_call_id);
+        if (run) run.result = m.tool_results;
+      }
+      continue;
+    }
+    const hasToolCalls = m.tool_calls != null && m.tool_calls.length > 0;
+    const hasText = m.content.length > 0;
+    if (m.role === 'assistant' && hasToolCalls) {
+      if (hasText || m.status === 'streaming') {
+        items.push({ kind: 'message', message: m });
+      }
+      for (const tc of m.tool_calls!) {
+        const run: ToolRun = { call: tc, result: null };
+        runsByCallId.set(tc.id, run);
+        items.push({ kind: 'tool_run', run, key: tc.id });
+      }
+      continue;
+    }
+    items.push({ kind: 'message', message: m });
+  }
+
+  return items;
+}
+
+// Second pass: collapse runs of >=GROUP_THRESHOLD consecutive tool_run items
+// of the same tool name into a single tool_group. Any other render item
+// (text bubble, sentinel, user message) breaks the chain.
+function group(items: RenderItem[]): RenderItem[] {
+  const out: RenderItem[] = [];
+  let i = 0;
+  while (i < items.length) {
+    const item = items[i]!;
+    if (item.kind !== 'tool_run') {
+      out.push(item);
+      i += 1;
+      continue;
+    }
+    const name = item.run.call.name;
+    let j = i + 1;
+    while (
+      j < items.length &&
+      items[j]!.kind === 'tool_run' &&
+      (items[j] as { kind: 'tool_run'; run: ToolRun }).run.call.name === name
+    ) {
+      j += 1;
+    }
+    const run = items.slice(i, j) as Array<{ kind: 'tool_run'; run: ToolRun; key: string }>;
+    if (run.length >= GROUP_THRESHOLD) {
+      out.push({
+        kind: 'tool_group',
+        runs: run.map((r) => r.run),
+        key: `group-${run[0]!.key}`,
+      });
+    } else {
+      for (const r of run) out.push(r);
+    }
+    i = j;
+  }
+  return out;
+}
+
+// Third pass: number cap-hit sentinels (1-indexed) and mark the latest.
+// CapHitSentinel uses position to compute the "N continues remaining"
+// tooltip, and isLatest to gate the Continue button (only the most recent
+// sentinel is actionable).
+function stampCapHits(items: RenderItem[]): RenderItem[] {
+  const totalCapHits = items.reduce(
+    (n, it) => n + (it.kind === 'message' && isCapHitSentinel(it.message) ? 1 : 0),
+    0,
+  );
+  if (totalCapHits === 0) return items;
+  let index = 0;
+  return items.map((it) => {
+    if (it.kind !== 'message' || !isCapHitSentinel(it.message)) return it;
+    index += 1;
+    return {
+      ...it,
+      capHitInfo: { position: index, isLatest: index === totalCapHits },
+    };
+  });
+}
+
 export function MessageList({ messages, sessionChats }: Props) {
   const endRef = useRef<HTMLDivElement>(null);
 
+  const renderItems = useMemo(() => stampCapHits(group(flatten(messages))), [messages]);
+
   useEffect(() => {
     endRef.current?.scrollIntoView({ block: 'end' });
   }, [messages]);
@@ -25,9 +138,22 @@ export function MessageList({ messages, sessionChats }: Props) {
   return (
     <div className="flex-1 overflow-y-auto">
       <div className="max-w-[1000px] mx-auto w-full px-6 py-4 space-y-4">
-        {messages.map((m) => (
-          <MessageBubble key={m.id} message={m} sessionChats={sessionChats} />
-        ))}
+        {renderItems.map((item) => {
+          if (item.kind === 'message') {
+            return (
+              <MessageBubble
+                key={item.message.id}
+                message={item.message}
+                sessionChats={sessionChats}
+                capHitInfo={item.capHitInfo}
+              />
+            );
+          }
+          if (item.kind === 'tool_run') {
+            return <ToolCallLine key={item.key} run={item.run} />;
+          }
+          return <ToolCallGroup key={item.key} runs={item.runs} />;
+        })}
         <div ref={endRef} />
       </div>
     </div>

apps/web/src/components/ToolCallCard.tsx

@@ -1,102 +0,0 @@
-import { useState } from 'react';
-import type { ReactNode } from 'react';
-import { ChevronRight, Wrench } from 'lucide-react';
-import type { Message, ToolCall } from '@/api/types';
-import { sessionEvents } from '@/hooks/sessionEvents';
-
-interface Props {
-  message?: Message;
-  toolCall?: ToolCall;
-}
-
-// Same regex/heuristic as MessageBubble: paths ending in `.ext` with at
-// least one `/`. Linkifies file paths emitted by tools like grep / find_files
-// so they're clickable.
-const PATH_REGEX = /([a-zA-Z0-9._/-]+\.[a-zA-Z0-9]+)/g;
-
-function linkifyOutput(text: string): ReactNode[] {
-  const out: ReactNode[] = [];
-  let lastIdx = 0;
-  let idx = 0;
-  for (const match of text.matchAll(PATH_REGEX)) {
-    const matchedText = match[0];
-    const start = match.index ?? 0;
-    if (!matchedText.includes('/')) continue;
-    if (start > lastIdx) out.push(text.slice(lastIdx, start));
-    out.push(
-      <button
-        key={idx}
-        type="button"
-        onClick={() =>
-          sessionEvents.emit({
-            type: 'open_file_in_browser',
-            path: matchedText,
-          })
-        }
-        className="text-primary underline cursor-pointer hover:text-primary/80"
-      >
-        {matchedText}
-      </button>
-    );
-    lastIdx = start + matchedText.length;
-    idx += 1;
-  }
-  if (lastIdx < text.length) out.push(text.slice(lastIdx));
-  return out.length > 0 ? out : [text];
-}
-
-export function ToolCallCard({ message, toolCall }: Props) {
-  const [open, setOpen] = useState(false);
-  const tc = toolCall ?? message?.tool_calls?.[0];
-  const result = message?.tool_results;
-
-  const name = tc?.name ?? 'tool';
-  const args = tc?.args ?? {};
-  const error = result?.error;
-  const output = result?.output;
-  const truncated = result?.truncated;
-
-  return (
-    <div className="rounded-md border border-border bg-muted/30 text-sm overflow-hidden">
-      <button
-        type="button"
-        onClick={() => setOpen((v) => !v)}
-        className="w-full flex items-center gap-2 px-2.5 py-1.5 hover:bg-muted/60 text-left"
-      >
-        <ChevronRight
-          className={`size-3.5 transition-transform ${open ? 'rotate-90' : ''}`}
-        />
-        <Wrench className="size-3.5 opacity-70" />
-        <span className="font-mono font-medium">{name}</span>
-        <span className="font-mono text-xs text-muted-foreground truncate min-w-0 flex-1">
-          {JSON.stringify(args)}
-        </span>
-        {error && (
-          <span className="text-xs text-destructive font-medium ml-2">error</span>
-        )}
-        {truncated && (
-          <span className="text-xs text-muted-foreground ml-2">truncated</span>
-        )}
-      </button>
-      {open && (
-        <div className="px-2.5 py-2 border-t bg-background/40">
-          {error ? (
-            <pre className="text-xs text-destructive font-mono whitespace-pre-wrap">
-              {error}
-            </pre>
-          ) : output !== undefined ? (
-            <pre className="text-xs font-mono whitespace-pre-wrap overflow-x-auto max-h-72 overflow-y-auto">
-              {linkifyOutput(
-                typeof output === 'string'
-                  ? output
-                  : JSON.stringify(output, null, 2)
-              )}
-            </pre>
-          ) : (
-            <div className="text-xs text-muted-foreground">no result yet</div>
-          )}
-        </div>
-      )}
-    </div>
-  );
-}

apps/web/src/components/ToolCallGroup.tsx

@@ -0,0 +1,64 @@
+import { useState } from 'react';
+import { ChevronRight } from 'lucide-react';
+import { ToolCallLine, runStatus, type ToolRun } from './ToolCallLine';
+
+interface Props {
+  // All runs must share the same tool name. Caller (MessageList grouping
+  // pass) enforces that invariant.
+  runs: ToolRun[];
+}
+
+export function ToolCallGroup({ runs }: Props) {
+  const [open, setOpen] = useState(false);
+  if (runs.length === 0) return null;
+  const toolName = runs[0]!.call.name;
+  const count = runs.length;
+
+  // Group-level status: pending if any are still running, error if any
+  // finished with an error, otherwise success. Matches the visual the user
+  // gets when scanning a long run of greps / view_files.
+  let pending = 0;
+  let errored = 0;
+  for (const r of runs) {
+    const s = runStatus(r);
+    if (s === 'pending') pending += 1;
+    else if (s === 'error') errored += 1;
+  }
+  const summaryParts: string[] = [];
+  if (pending > 0) summaryParts.push(`${pending} running`);
+  if (errored > 0) summaryParts.push(`${errored} failed`);
+  const summary = summaryParts.length > 0 ? ` (${summaryParts.join(', ')})` : '';
+
+  return (
+    <div className="rounded border border-border/60 bg-muted/20 text-xs">
+      <button
+        type="button"
+        onClick={() => setOpen((v) => !v)}
+        className="w-full flex items-center gap-1.5 px-2 py-1 hover:bg-muted/40 text-left"
+      >
+        <ChevronRight
+          className={`size-3 text-muted-foreground/60 shrink-0 transition-transform ${open ? 'rotate-90' : ''}`}
+        />
+        <span className="text-muted-foreground/60 select-none shrink-0">⊞</span>
+        <span className="font-mono text-foreground/90">
+          {count} {toolName} call{count === 1 ? '' : 's'}
+        </span>
+        {summary && (
+          <span className="text-muted-foreground truncate">{summary}</span>
+        )}
+        <span className="ml-auto text-muted-foreground/60 shrink-0">tap</span>
+      </button>
+      {open && (
+        <div className="border-t border-border/40 px-2 py-1 space-y-0.5">
+          {runs.map((run, i) => (
+            <ToolCallLine
+              key={`${run.call.id}-${i}`}
+              run={run}
+              insideGroup
+            />
+          ))}
+        </div>
+      )}
+    </div>
+  );
+}

apps/web/src/components/ToolCallLine.tsx

@@ -0,0 +1,167 @@
+import { useState } from 'react';
+import type { ReactNode } from 'react';
+import { Check, ChevronRight, Loader2, X } from 'lucide-react';
+import type { ToolCall, ToolResult } from '@/api/types';
+import { sessionEvents } from '@/hooks/sessionEvents';
+
+// v1.8.2: cap on the inline arg-summary length. Expanded view shows full
+// args + full result, so this is purely a single-line render budget.
+const ARG_SUMMARY_MAX = 60;
+
+export interface ToolRun {
+  call: ToolCall;
+  // null while the call is in flight or the matching tool result hasn't
+  // arrived yet on the WS stream.
+  result: ToolResult | null;
+}
+
+function truncate(s: string, n: number): string {
+  return s.length > n ? s.slice(0, n - 1) + '…' : s;
+}
+
+// Per-tool argument summary mapping from the v1.8.2 spec. Goal is a single
+// scannable line that surfaces the *what* (path / pattern) without
+// overwhelming the chat with full JSON.
+export function formatToolArgs(name: string, args: Record<string, unknown>): string {
+  if (name === 'view_file') {
+    const path = String(args.path ?? '');
+    const start = args.start_line;
+    const end = args.end_line;
+    if (typeof start === 'number' && typeof end === 'number') {
+      return truncate(`${path}:${start}-${end}`, ARG_SUMMARY_MAX);
+    }
+    if (typeof start === 'number') {
+      return truncate(`${path}:${start}`, ARG_SUMMARY_MAX);
+    }
+    return truncate(path, ARG_SUMMARY_MAX);
+  }
+  if (name === 'list_dir') {
+    return truncate(String(args.path ?? '.'), ARG_SUMMARY_MAX);
+  }
+  if (name === 'grep') {
+    const pattern = String(args.pattern ?? '');
+    const path = args.path ? ` ${String(args.path)}` : '';
+    return truncate(`"${pattern}"${path}`, ARG_SUMMARY_MAX);
+  }
+  if (name === 'find_files') {
+    return truncate(String(args.pattern ?? ''), ARG_SUMMARY_MAX);
+  }
+  if (name === 'git_status') {
+    return '';
+  }
+  // Unknown tool — surface first arg value or the literal {} so the user can
+  // see something happened. Forward-compatible with future tools.
+  const keys = Object.keys(args);
+  if (keys.length === 0) return '{}';
+  const first = keys[0]!;
+  return truncate(`${first}: ${String(args[first])}`, ARG_SUMMARY_MAX);
+}
+
+export function runStatus(run: ToolRun): 'pending' | 'success' | 'error' {
+  if (run.result === null) return 'pending';
+  if (run.result.error) return 'error';
+  return 'success';
+}
+
+// Path-shaped paths in tool output text get a click handler so users can
+// jump to the file. Same heuristic as MessageBubble.linkifyPaths.
+const PATH_REGEX = /([a-zA-Z0-9._/-]+\.[a-zA-Z0-9]+)/g;
+function linkifyOutput(text: string): ReactNode[] {
+  const out: ReactNode[] = [];
+  let lastIdx = 0;
+  let idx = 0;
+  for (const match of text.matchAll(PATH_REGEX)) {
+    const matchedText = match[0];
+    const start = match.index ?? 0;
+    if (!matchedText.includes('/')) continue;
+    if (start > lastIdx) out.push(text.slice(lastIdx, start));
+    out.push(
+      <button
+        key={idx}
+        type="button"
+        onClick={() =>
+          sessionEvents.emit({ type: 'open_file_in_browser', path: matchedText })
+        }
+        className="text-primary underline cursor-pointer hover:text-primary/80"
+      >
+        {matchedText}
+      </button>
+    );
+    lastIdx = start + matchedText.length;
+    idx += 1;
+  }
+  if (lastIdx < text.length) out.push(text.slice(lastIdx));
+  return out.length > 0 ? out : [text];
+}
+
+interface Props {
+  run: ToolRun;
+  // When rendered inside a ToolCallGroup the line is already nested under a
+  // shared header, so the leading arrow is dropped to avoid double indent.
+  insideGroup?: boolean;
+}
+
+export function ToolCallLine({ run, insideGroup }: Props) {
+  const [open, setOpen] = useState(false);
+  const status = runStatus(run);
+  const args = run.call.args ?? {};
+  const summary = formatToolArgs(run.call.name, args);
+
+  return (
+    <div className="text-xs">
+      <button
+        type="button"
+        onClick={() => setOpen((v) => !v)}
+        className="flex items-center gap-1.5 w-full text-left hover:bg-muted/40 rounded px-1 py-0.5 -mx-1"
+      >
+        {!insideGroup && (
+          <span className="text-muted-foreground/60 select-none shrink-0">↳</span>
+        )}
+        <ChevronRight
+          className={`size-3 text-muted-foreground/60 shrink-0 transition-transform ${open ? 'rotate-90' : ''}`}
+        />
+        <span className="font-mono text-foreground/90 shrink-0">{run.call.name}</span>
+        {summary && (
+          <span className="font-mono text-muted-foreground truncate min-w-0 flex-1">
+            {summary}
+          </span>
+        )}
+        {!summary && <span className="flex-1" />}
+        <span className="shrink-0 ml-1">
+          {status === 'pending' && (
+            <Loader2 className="size-3 text-muted-foreground animate-spin" aria-label="running" />
+          )}
+          {status === 'success' && (
+            <Check className="size-3 text-emerald-500" aria-label="success" />
+          )}
+          {status === 'error' && (
+            <X className="size-3 text-destructive" aria-label="error" />
+          )}
+        </span>
+      </button>
+      {open && (
+        <div className="ml-5 mt-1 mb-1 space-y-1">
+          <pre className="text-[10px] text-muted-foreground font-mono whitespace-pre-wrap break-all bg-muted/30 rounded px-2 py-1">
+            {JSON.stringify(args, null, 2)}
+          </pre>
+          {run.result && (
+            <pre className="text-[11px] font-mono whitespace-pre-wrap bg-muted/30 rounded px-2 py-1 max-h-72 overflow-y-auto">
+              {run.result.error ? (
+                <span className="text-destructive">{run.result.error}</span>
+              ) : (
+                linkifyOutput(
+                  typeof run.result.output === 'string'
+                    ? run.result.output
+                    : JSON.stringify(run.result.output, null, 2)
+                )
+              )}
+              {run.result.truncated && (
+                <div className="text-muted-foreground/60 mt-1">— output truncated —</div>
+              )}
+            </pre>
+          )}
+        </div>
+      )}
+    </div>
+  );
+}

apps/web/src/hooks/sessionEvents.ts

@@ -2,7 +2,7 @@
 // across hooks (e.g. AI rename arriving via WS in the session view needs to
 // also refresh the sidebar's session list).
 
-import type { Chat, Project, Session } from '@/api/types';
+import type { Chat, ErrorReason, Project, Session } from '@/api/types';
 import type { Attachment } from '@/lib/attachments';
 
 export interface SessionRenamedEvent {
@@ -118,11 +118,14 @@ export interface ProjectUpdatedEvent {
 // v1.8 mobile-tabs: broadcast on user channel from inference.ts so any device
 // subscribed sees a chat working/idle/error. Frontend stores per-chat; panes
 // derive their dot from pane.activeChatId.
+// v1.8.2: optional `reason` carries a machine-readable code when status is
+// 'error'. UI prefers reason for inline error rendering.
 export interface ChatStatusEvent {
   type: 'chat_status';
   chat_id: string;
   status: 'working' | 'idle' | 'error';
   at: string;
+  reason?: ErrorReason;
 }
 
 export type SessionEvent =

apps/web/src/hooks/useSessionStream.ts

@@ -29,7 +29,9 @@ function applyFrame(state: State, frame: WsFrame): State {
         kind: 'message',
         tool_calls: null,
         tool_results: null,
-        status: 'streaming',
+        // v1.8.2: cap-hit sentinels arrive role='system' and are static, so
+        // skipping the streaming dot for them keeps the UI accurate.
+        status: frame.role === 'system' ? 'complete' : 'streaming',
         last_seq: 0,
         tokens_used: null,
         ctx_used: null,
@@ -37,6 +39,7 @@ function applyFrame(state: State, frame: WsFrame): State {
         started_at: null,
         finished_at: null,
         created_at: new Date().toISOString(),
+        metadata: null,
       };
       return { ...state, messages: [...state.messages, newMsg] };
     }
@@ -96,6 +99,7 @@ function applyFrame(state: State, frame: WsFrame): State {
         started_at: null,
         finished_at: null,
         created_at: new Date().toISOString(),
+        metadata: null,
       };
       return { ...state, messages: [...state.messages, newMsg] };
     }
@@ -110,6 +114,10 @@ function applyFrame(state: State, frame: WsFrame): State {
               ...(frame.ctx_max !== undefined ? { ctx_max: frame.ctx_max } : {}),
               ...(frame.started_at !== undefined ? { started_at: frame.started_at } : {}),
               ...(frame.finished_at !== undefined ? { finished_at: frame.finished_at } : {}),
+              // v1.8.2: cap-hit sentinels (and future stamped metadata) ride
+              // in on this terminal frame so the reducer can attach it
+              // without waiting for a refetch.
+              ...(frame.metadata !== undefined ? { metadata: frame.metadata } : {}),
             }
           : m
       );
@@ -133,9 +141,22 @@ function applyFrame(state: State, frame: WsFrame): State {
       return state;
     }
     case 'error': {
+      // v1.8.2: when the frame carries a structured reason, stamp it onto the
+      // failed message's metadata so the bubble can render specifics inline
+      // (the WS error frame is one-shot; refresh-safe rendering needs the
+      // value persisted on the message).
+      const errorMeta = frame.reason
+        ? { kind: 'error' as const, error_reason: frame.reason, error_text: frame.error }
+        : null;
       const next = frame.message_id
         ? state.messages.map((m) =>
-            m.id === frame.message_id ? { ...m, status: 'failed' as const } : m
+            m.id === frame.message_id
+              ? {
+                  ...m,
+                  status: 'failed' as const,
+                  ...(errorMeta ? { metadata: errorMeta } : {}),
+                }
+              : m
           )
         : state.messages;
       return { ...state, messages: next, error: frame.error };

boocode_roadmap.md

@@ -323,6 +323,10 @@ Full inventory in `boocode_code_review.md`. Headline items:
 - **codeprysm rejected** — embedding-based; node/edge taxonomy noted as reference if we ever build our own graph.
 - **Batch 9 decoupled from Batch 7 (2026-05-16).** AgentPicker mounts in `ChatInput.tsx` toolbar only. SettingsDrawer agent entry and Header active-agent badge moved to Batch 7. Builtin defaults shipped: six agents (Code Reviewer, Debugger, Refactorer, Architect, Security Auditor, Prompt Builder) with no `model` field — session model wins by default.
 
+## Follow-ups (post-ship docs / cleanup)
+
+- **After v1.8.2 ships:** Add explicit `max_tool_calls: 30` to all 6 agents in `/data/AGENTS.md` and `/opt/boocode/AGENTS.md`. Purely for documentation/discoverability — defaults handle behavior identically (all 6 agents use only read-only tools, default is already 30).
+
 -----
 
 ## Workflow