fix(agent): stop tool thrash after writes and log rounds

Cap get_api_docs, break duplicate tool rounds, force a reply after
successful writes, and log each tool call so limit hits are diagnosable.

src/modules/agent/assistant-chat-storage.ts

@@ -4,6 +4,7 @@ export type AssistantChatMessage = {
   role: "user" | "assistant";
   content: string;
   imageUrl?: string;
+  toolCalls?: Array<{ name: string; status: number }>;
 };
 
 const STORAGE_VERSION = "v2";
@@ -19,6 +20,14 @@ function isValidMessage(value: unknown): value is AssistantChatMessage {
   if (row.role !== "user" && row.role !== "assistant") return false;
   if (typeof row.content !== "string" || row.content.trim().length === 0) return false;
   if (row.imageUrl !== undefined && typeof row.imageUrl !== "string") return false;
+  if (row.toolCalls !== undefined) {
+    if (!Array.isArray(row.toolCalls)) return false;
+    for (const call of row.toolCalls) {
+      if (!call || typeof call !== "object") return false;
+      const entry = call as Record<string, unknown>;
+      if (typeof entry.name !== "string" || typeof entry.status !== "number") return false;
+    }
+  }
   return true;
 }
 

src/modules/agent/components/assistant-panel.tsx

@@ -229,7 +229,11 @@ export function AssistantPanel({ configured, userId, assistantName, assistantMod
 
       setMessages((current) => [
         ...current,
-        { role: "assistant", content: result.message.content },
+        {
+          role: "assistant",
+          content: result.message.content,
+          ...(result.toolCalls.length > 0 ? { toolCalls: result.toolCalls } : {}),
+        },
       ]);
       scrollToBottom();
     } catch (err) {
@@ -347,6 +351,13 @@ export function AssistantPanel({ configured, userId, assistantName, assistantMod
                   />
                 ) : null}
                 {message.content}
+                {message.role === "assistant" &&
+                message.toolCalls &&
+                message.toolCalls.length > 0 ? (
+                  <p className="mt-1 text-[10px] text-muted-foreground">
+                    {message.toolCalls.map((call) => `${call.name}→${call.status}`).join(" · ")}
+                  </p>
+                ) : null}
               </div>
             ))}
 

src/modules/agent/server/loop-guards.ts

@@ -0,0 +1,85 @@
+const MUTATION_TOOLS = new Set([
+  "add_list_item",
+  "update_list_item",
+  "delete_list_item",
+  "create_list",
+  "update_list",
+  "delete_list",
+  "create_event",
+  "update_event",
+  "delete_event",
+  "create_calendar",
+  "create_note",
+  "update_note",
+  "delete_note",
+  "create_journal_entry",
+  "update_journal_entry",
+  "delete_journal_entry",
+  "create_garden_plant",
+  "update_garden_plant",
+  "delete_garden_plant",
+  "create_garden_container",
+  "update_garden_container",
+  "delete_garden_container",
+  "log_garden_care",
+  "create_garden_care_schedule",
+  "update_garden_care_schedule",
+  "delete_garden_care_schedule",
+  "schedule_garden_care_on_calendar",
+  "create_bang",
+  "update_bang",
+  "delete_bang",
+  "create_share_link",
+  "revoke_share_link",
+]);
+
+export function isMutationTool(name: string): boolean {
+  return MUTATION_TOOLS.has(name);
+}
+
+export function isSuccessfulWrite(name: string, status: number, argsJson = ""): boolean {
+  if (!isSuccessfulStatus(status)) return false;
+  if (isMutationTool(name)) return true;
+  if (name !== "call_api") return false;
+  try {
+    const args = JSON.parse(argsJson || "{}") as { method?: string };
+    const method = typeof args.method === "string" ? args.method.toUpperCase() : "";
+    return method === "POST" || method === "PATCH" || method === "DELETE";
+  } catch {
+    return false;
+  }
+}
+
+export function isSuccessfulStatus(status: number): boolean {
+  return status >= 200 && status < 300;
+}
+
+export function fingerprintToolCalls(calls: Array<{ name: string; arguments: string }>): string {
+  return calls.map((call) => `${call.name}:${normalizeArgs(call.arguments)}`).join("|");
+}
+
+export function truncateToolResult(result: string, maxChars = 6000): string {
+  if (result.length <= maxChars) return result;
+  return `${result.slice(0, maxChars)}\n…[truncated ${result.length - maxChars} chars]`;
+}
+
+export function summarizeToolTrace(toolCalls: Array<{ name: string; status: number }>): string {
+  if (toolCalls.length === 0) return "No tools were called.";
+  return toolCalls.map((call) => `${call.name}→${call.status}`).join(", ");
+}
+
+function normalizeArgs(argsJson: string): string {
+  try {
+    const parsed: unknown = JSON.parse(argsJson || "{}");
+    if (!parsed || typeof parsed !== "object" || Array.isArray(parsed)) {
+      return JSON.stringify(parsed);
+    }
+    const sorted: Record<string, unknown> = {};
+    for (const key of Object.keys(parsed as Record<string, unknown>).sort()) {
+      sorted[key] = (parsed as Record<string, unknown>)[key];
+    }
+    return JSON.stringify(sorted);
+  } catch {
+    return argsJson.trim();
+  }
+}

src/modules/agent/server/run.ts

@@ -1,9 +1,16 @@
+import logger from "@/lib/logger";
 import { createLlmClient, type ChatMessage, type LlmClient } from "@/lib/llm";
 import { buildVisionContentParts, textFromMessageContent } from "@/lib/llm/content";
 import { AGENT_SYSTEM_PROMPT, AGENT_TOOLS, appendAgentRuntimeContext } from "../tools";
 import type { ClientChatMessage } from "../messages";
 import { describeToolActivity } from "../tool-labels";
 import { createApiToolExecutor, type ToolExecutor } from "../tool-executor";
+import {
+  fingerprintToolCalls,
+  isSuccessfulWrite,
+  summarizeToolTrace,
+  truncateToolResult,
+} from "./loop-guards";
 import { resolveAssistantImageDataUrls } from "./resolve-images";
 import { thinkingLabel, type AgentProgressEvent } from "./progress";
 
@@ -41,6 +48,21 @@ async function toLlmUserMessage(message: ClientChatMessage): Promise<ChatMessage
   };
 }
 
+function forceReplyAfterWrite(writeNames: string[]): ChatMessage {
+  return {
+    role: "user",
+    content: `The write already succeeded (${writeNames.join(", ")}). Stop calling tools and reply to the user in one short sentence confirming what you did.`,
+  };
+}
+
+function forceReplyAfterRepeat(): ChatMessage {
+  return {
+    role: "user",
+    content:
+      "You repeated the same tool call. Stop calling tools and reply with what you already know, or ask one clarifying question.",
+  };
+}
+
 export async function runAgentChat(options: {
   messages: ClientChatMessage[];
   request: Request;
@@ -62,13 +84,16 @@ export async function runAgentChat(options: {
   const transcript: ChatMessage[] = [{ role: "system", content: systemPrompt }, ...userMessages];
 
   const toolCalls: AgentToolCallSummary[] = [];
+  const seenFingerprints = new Set<string>();
+  const successfulWriteNames: string[] = [];
+  let forceReply = false;
 
   for (let round = 0; round < MAX_TOOL_ROUNDS; round += 1) {
     onProgress?.({ type: "thinking", label: thinkingLabel(round), round });
 
     const completion = await llm.chatCompletion({
       messages: transcript,
-      tools: AGENT_TOOLS,
+      tools: forceReply ? undefined : AGENT_TOOLS,
     });
 
     const assistantMessage = completion.message;
@@ -76,6 +101,15 @@ export async function runAgentChat(options: {
 
     if (!assistantMessage.tool_calls?.length) {
       onProgress?.({ type: "responding", label: "Writing a reply…" });
+      logger.info(
+        {
+          msg: "agent.chat.done",
+          rounds: round + 1,
+          toolCalls: toolCalls.map((call) => `${call.name}:${call.status}`),
+          forcedReply: forceReply,
+        },
+        "agent chat completed",
+      );
       return {
         message: {
           role: "assistant",
@@ -87,6 +121,36 @@ export async function runAgentChat(options: {
       };
     }
 
+    if (forceReply) {
+      logger.warn(
+        {
+          msg: "agent.chat.forced_tools_ignored",
+          round,
+          names: assistantMessage.tool_calls.map((c) => c.function.name),
+        },
+        "model kept calling tools after force-reply",
+      );
+      break;
+    }
+
+    const fingerprint = fingerprintToolCalls(
+      assistantMessage.tool_calls.map((call) => ({
+        name: call.function.name,
+        arguments: call.function.arguments,
+      })),
+    );
+
+    if (seenFingerprints.has(fingerprint)) {
+      logger.warn(
+        { msg: "agent.chat.duplicate_tools", round, fingerprint, toolCalls: fingerprint },
+        "duplicate tool round detected",
+      );
+      transcript.push(forceReplyAfterRepeat());
+      forceReply = true;
+      continue;
+    }
+    seenFingerprints.add(fingerprint);
+
     for (const toolCall of assistantMessage.tool_calls) {
       const label = describeToolActivity(toolCall.function.name, toolCall.function.arguments);
       onProgress?.({ type: "tool", name: toolCall.function.name, label });
@@ -107,21 +171,69 @@ export async function runAgentChat(options: {
       }
 
       toolCalls.push({ name: toolCall.function.name, status });
+      logger.info(
+        {
+          msg: "agent.chat.tool",
+          round,
+          name: toolCall.function.name,
+          status,
+          args: toolCall.function.arguments.slice(0, 300),
+        },
+        "agent tool call",
+      );
+
+      if (isSuccessfulWrite(toolCall.function.name, status, toolCall.function.arguments)) {
+        successfulWriteNames.push(toolCall.function.name);
+      }
 
       transcript.push({
         role: "tool",
         tool_call_id: toolCall.id,
         name: toolCall.function.name,
-        content: result,
+        content: truncateToolResult(result),
       });
     }
+
+    if (successfulWriteNames.length > 0) {
+      transcript.push(forceReplyAfterWrite(successfulWriteNames));
+      forceReply = true;
+    }
   }
 
   onProgress?.({ type: "responding", label: "Wrapping up…" });
+  const trace = summarizeToolTrace(toolCalls);
+
+  if (successfulWriteNames.length > 0) {
+    logger.warn(
+      {
+        msg: "agent.chat.forced_summary",
+        rounds: MAX_TOOL_ROUNDS,
+        toolCalls: toolCalls.map((call) => `${call.name}:${call.status}`),
+      },
+      "agent summarizing after write without clean stop",
+    );
+    return {
+      message: {
+        role: "assistant",
+        content: `Done. Completed: ${[...new Set(successfulWriteNames)].join(", ")}.`,
+      },
+      toolCalls,
+    };
+  }
+
+  logger.warn(
+    {
+      msg: "agent.chat.tool_limit",
+      rounds: MAX_TOOL_ROUNDS,
+      toolCalls: toolCalls.map((call) => `${call.name}:${call.status}`),
+      forcedReply: forceReply,
+    },
+    "agent hit tool-call limit",
+  );
   return {
     message: {
       role: "assistant",
-      content: "I hit the tool-call limit for this request. Please try a simpler question.",
+      content: `I hit the tool-call limit for this request. Tools used: ${trace}.`,
     },
     toolCalls,
   };

src/modules/agent/tool-executor.ts

@@ -451,13 +451,18 @@ async function getApiDocs(args: Record<string, unknown>): Promise<ApiCallResult>
   const specPath = path.join(process.cwd(), "docs", "api", "openapi.yaml");
   const spec = await readFile(specPath, "utf8");
   const search = typeof args.search === "string" ? args.search.trim().toLowerCase() : "";
+  const pathLines = spec
+    .split("\n")
+    .map((line) => line.trim())
+    .filter((line) => line.startsWith("/api/v1/"));
 
   if (!search) {
     return {
       status: 200,
       body: {
-        spec,
+        paths: pathLines.slice(0, 80),
-        hint: "Pass search to filter paths, or use call_api with a /api/v1/* path.",
+        pathCount: pathLines.length,
+        hint: "Pass search (e.g. calendar, events, lists) to get matching lines. Do not request the full OpenAPI dump.",
       },
     };
   }
@@ -469,8 +474,8 @@ async function getApiDocs(args: Record<string, unknown>): Promise<ApiCallResult>
     body: {
       search,
       matchCount: matches.length,
-      matches: matches.slice(0, 100),
+      matches: matches.slice(0, 40),
-      hint: "Use call_api with method and path from the matches above.",
+      hint: "Use a dedicated tool when one exists; otherwise call_api with method and path from the matches above.",
     },
   };
 }

src/modules/agent/tools.ts

@@ -718,15 +718,16 @@ export const AGENT_TOOLS: AgentToolDefinition[] = [
     function: {
       name: "get_api_docs",
       description:
-        "Read famapp REST API documentation (OpenAPI). Use when unsure which endpoint to call or no dedicated tool exists. Pass search to filter relevant paths.",
+        "Search famapp REST API docs for /api/v1 paths. Always pass search. Returns matching lines only — not the full OpenAPI file.",
       parameters: {
         type: "object",
         properties: {
           search: {
             type: "string",
-            description: "Optional keyword to filter paths (e.g. garden, share, journal)",
+            description: "Keyword to filter paths (e.g. garden, share, journal, events)",
           },
         },
+        required: ["search"],
       },
     },
   },
@@ -767,10 +768,11 @@ export const AGENT_SYSTEM_PROMPT = `You are the famapp household assistant. Help
 
 Use the provided tools to read and update data. Prefer calling tools instead of guessing. Be concise and friendly.
 
-Prefer a dedicated tool when one exists (create_event, add_list_item, create_note, etc.). When no dedicated tool fits, or you need an endpoint that is not wrapped yet:
+Prefer a dedicated tool when one exists (create_event, add_list_item, create_note, etc.). After a successful write (2xx), stop calling tools and confirm in one short sentence — do not re-list or re-create.
-1. Call get_api_docs with a relevant search term to find the right /api/v1/* endpoint.
+When no dedicated tool fits, or you need an endpoint that is not wrapped yet:
+1. Call get_api_docs with a relevant search term (always pass search; never request the full spec).
 2. Call call_api with the documented method, path, query, and body.
-If a tool call fails, read the error body and fix the arguments before trying a different approach.
+If a tool call fails, read the error body and fix the arguments before trying a different approach. Do not repeat the exact same tool call.
 
 When the user sends a photo, read dates, times, locations, and action items from it, then use tools to act.
 

tests/unit/agent-loop-guards.test.ts

@@ -0,0 +1,152 @@
+import assert from "node:assert/strict";
+import { describe, it } from "node:test";
+import {
+  fingerprintToolCalls,
+  isSuccessfulWrite,
+  summarizeToolTrace,
+  truncateToolResult,
+} from "../../src/modules/agent/server/loop-guards";
+import { runAgentChat } from "../../src/modules/agent/server/run";
+import type {
+  ChatCompletionRequest,
+  ChatCompletionResult,
+  LlmClient,
+} from "../../src/lib/llm/types";
+
+describe("loop-guards", () => {
+  it("fingerprints tool calls stably regardless of key order", () => {
+    const a = fingerprintToolCalls([
+      { name: "create_event", arguments: '{"title":"Dentist","calendarName":"Family"}' },
+    ]);
+    const b = fingerprintToolCalls([
+      { name: "create_event", arguments: '{"calendarName":"Family","title":"Dentist"}' },
+    ]);
+    assert.equal(a, b);
+  });
+
+  it("treats create_event 201 as a successful write", () => {
+    assert.equal(isSuccessfulWrite("create_event", 201), true);
+    assert.equal(isSuccessfulWrite("list_calendars", 200), false);
+    assert.equal(
+      isSuccessfulWrite("call_api", 201, '{"method":"POST","path":"/api/v1/events"}'),
+      true,
+    );
+    assert.equal(
+      isSuccessfulWrite("call_api", 200, '{"method":"GET","path":"/api/v1/events"}'),
+      false,
+    );
+  });
+
+  it("truncates oversized tool results", () => {
+    const result = truncateToolResult("x".repeat(7000), 100);
+    assert.ok(result.length < 200);
+    assert.match(result, /truncated/);
+  });
+
+  it("summarizes tool traces", () => {
+    assert.equal(
+      summarizeToolTrace([
+        { name: "list_calendars", status: 200 },
+        { name: "create_event", status: 201 },
+      ]),
+      "list_calendars→200, create_event→201",
+    );
+  });
+});
+
+describe("runAgentChat loop guards", () => {
+  it("stops after a successful write instead of looping", async () => {
+    let calls = 0;
+    const llm: LlmClient = {
+      async chatCompletion(request: ChatCompletionRequest): Promise<ChatCompletionResult> {
+        calls += 1;
+        if (calls === 1) {
+          return {
+            message: {
+              role: "assistant",
+              content: null,
+              tool_calls: [
+                {
+                  id: "1",
+                  type: "function",
+                  function: {
+                    name: "create_event",
+                    arguments: JSON.stringify({
+                      title: "Dentist",
+                      startAt: "2026-07-10T15:00:00.000Z",
+                      endAt: "2026-07-10T16:00:00.000Z",
+                    }),
+                  },
+                },
+              ],
+            },
+            finishReason: "tool_calls",
+          };
+        }
+
+        assert.equal(request.tools, undefined);
+        return {
+          message: { role: "assistant", content: "Added Dentist to your calendar." },
+          finishReason: "stop",
+        };
+      },
+    };
+
+    const result = await runAgentChat({
+      messages: [{ role: "user", content: "add dentist tomorrow at 10" }],
+      request: new Request("http://localhost:3000/api/agent/chat"),
+      llm,
+      executeTool: async () =>
+        JSON.stringify({ status: 201, body: { id: "evt-1", title: "Dentist" } }),
+    });
+
+    assert.equal(calls, 2);
+    assert.equal(result.toolCalls.length, 1);
+    assert.equal(result.toolCalls[0]?.name, "create_event");
+    assert.match(result.message.content, /Dentist/);
+  });
+
+  it("breaks duplicate identical tool rounds", async () => {
+    let calls = 0;
+    const llm: LlmClient = {
+      async chatCompletion(): Promise<ChatCompletionResult> {
+        calls += 1;
+        if (calls <= 2) {
+          return {
+            message: {
+              role: "assistant",
+              content: null,
+              tool_calls: [
+                {
+                  id: String(calls),
+                  type: "function",
+                  function: {
+                    name: "list_calendars",
+                    arguments: "{}",
+                  },
+                },
+              ],
+            },
+            finishReason: "tool_calls",
+          };
+        }
+        return {
+          message: { role: "assistant", content: "You have one Family calendar." },
+          finishReason: "stop",
+        };
+      },
+    };
+
+    const result = await runAgentChat({
+      messages: [{ role: "user", content: "what calendars do I have?" }],
+      request: new Request("http://localhost:3000/api/agent/chat"),
+      llm,
+      executeTool: async () =>
+        JSON.stringify({ status: 200, body: [{ id: "cal-1", name: "Family" }] }),
+    });
+
+    assert.equal(calls, 3);
+    assert.equal(result.toolCalls.length, 1);
+    assert.match(result.message.content, /Family/);
+  });
+});