chore: release v0.6.5

Tool self-fetches were hairpinning to fam.ginnoir.com and failing,
so list_calendars/create_event returned 500 and the model gave up.

.env.example

@@ -55,3 +55,7 @@ LLM_PROVIDER=openai
 LLM_BASE_URL=
 LLM_API_KEY=
 LLM_MODEL=llama3.2
+# IANA timezone for assistant relative dates ("Thursday at 2"). Falls back to TZ, then America/Chicago.
+HOUSEHOLD_TIMEZONE=America/Chicago
+# Optional override for agent tool → /api/v1 self-calls (defaults to http://127.0.0.1:$PORT).
+# INTERNAL_API_BASE_URL=http://127.0.0.1:3000

CHANGELOG.md

@@ -1,5 +1,23 @@
 # Changelog
 
+## [0.6.5](https://github.com/ginnoir/famapp/compare/v0.6.4...v0.6.5) (2026-07-09)
+
+### Bug Fixes
+
+- **agent:** call api v1 via loopback instead of public url ([3e8fe2d](https://github.com/ginnoir/famapp/commit/3e8fe2d06dc31d3a1058b4b8942c46b1220a6b4c))
+
+## [0.6.4](https://github.com/ginnoir/famapp/compare/v0.6.3...v0.6.4) (2026-07-09)
+
+### Bug Fixes
+
+- **agent:** stop tool thrash after writes and log rounds ([72d123b](https://github.com/ginnoir/famapp/commit/72d123b9a0f67589d92614a8d2138912585b0d79))
+
+## [0.6.3](https://github.com/ginnoir/famapp/compare/v0.6.2...v0.6.3) (2026-07-09)
+
+### Bug Fixes
+
+- **agent:** raise tool rounds and ease calendar creates ([d3e79ed](https://github.com/ginnoir/famapp/commit/d3e79edb9ef0b931fa9d6e6629dad2677d661741))
+
 ## [0.6.2](https://github.com/ginnoir/famapp/compare/v0.6.1...v0.6.2) (2026-07-09)
 
 ### Features

STATUS.md

@@ -111,5 +111,6 @@ P2/P3 backlog is filed on Gitea only (no task briefs yet) — see `docs/issues-m
 - Repo: https://github.com/ginnoir/famapp (HTTPS remote on `origin`).
 - Local dev tooling installed: Node 22+, pnpm 10.33.3.
 - `.env` is **not** committed; copy `.env.example` → `.env` when needed.
+- Assistant relative dates use `HOUSEHOLD_TIMEZONE` (default `America/Chicago` if unset).
 - VS Code recommended extensions in `.vscode/extensions.json`; copy `.vscode/settings.json.example` → `.vscode/settings.json` for the workspace defaults.
 - Memory files (cross-session, only seen by Claude): `C:\Users\MattC\.claude\projects\C--Users-MattC-Documents-famapp\memory\`.

package.json

@@ -1,6 +1,6 @@
 {
   "name": "famapp",
-  "version": "0.6.2",
+  "version": "0.6.5",
   "private": true,
   "type": "module",
   "packageManager": "pnpm@10.33.3",

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

@@ -1,13 +1,20 @@
+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 } from "../tools";
+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";
 
-const MAX_TOOL_ROUNDS = 8;
+const MAX_TOOL_ROUNDS = 24;
 
 export type AgentToolCallSummary = {
   name: string;
@@ -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;
@@ -53,7 +75,7 @@ export async function runAgentChat(options: {
   const llm = options.llm ?? createLlmClient({ model: options.model });
   const executeTool = options.executeTool ?? createApiToolExecutor(options.request);
   const onProgress = options.onProgress;
-  const systemPrompt = options.systemPrompt ?? AGENT_SYSTEM_PROMPT;
+  const systemPrompt = appendAgentRuntimeContext(options.systemPrompt ?? AGENT_SYSTEM_PROMPT);
 
   const userMessages = await Promise.all(
     options.messages.map((message) => toLlmUserMessage(message)),
@@ -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 });
@@ -96,8 +160,20 @@ export async function runAgentChat(options: {
 
       try {
         result = await executeTool(toolCall.function.name, toolCall.function.arguments);
-        const parsed = JSON.parse(result) as { status?: number };
+        const parsed = JSON.parse(result) as { status?: number; body?: unknown };
         status = typeof parsed.status === "number" ? parsed.status : 200;
+        if (status >= 400) {
+          logger.warn(
+            {
+              msg: "agent.chat.tool_error",
+              round,
+              name: toolCall.function.name,
+              status,
+              body: parsed.body,
+            },
+            "agent tool returned error",
+          );
+        }
       } catch (err) {
         status = 500;
         result = JSON.stringify({
@@ -107,21 +183,69 @@ 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

@@ -1,3 +1,5 @@
+import logger from "@/lib/logger";
+
 type ApiCallResult = {
   status: number;
   body: unknown;
@@ -5,8 +7,22 @@ type ApiCallResult = {
 
 export type ToolExecutor = (name: string, argsJson: string) => Promise<string>;
 
+/** Loopback base for in-process tool → /api/v1 calls. Avoids hairpinning to the public URL. */
+export function resolveInternalApiBase(request: Request): string {
+  const configured = process.env.INTERNAL_API_BASE_URL?.trim();
+  if (configured) return configured.replace(/\/$/, "");
+
+  const port = process.env.PORT?.trim() || "3000";
+  const requestUrl = new URL(request.url);
+  if (requestUrl.hostname === "localhost" || requestUrl.hostname === "127.0.0.1") {
+    return requestUrl.origin;
+  }
+
+  return `http://127.0.0.1:${port}`;
+}
+
 export function createApiToolExecutor(request: Request): ToolExecutor {
-  const origin = new URL(request.url).origin;
+  const origin = resolveInternalApiBase(request);
 
   return async (name: string, argsJson: string) => {
     const args = parseArgs(argsJson);
@@ -111,8 +127,11 @@ async function dispatchTool(
       return callApi(request, origin, "GET", `/api/v1/events?${qs.toString()}`);
     }
     case "create_event": {
+      const resolved = await resolveCalendarId(args, request, origin);
+      if ("error" in resolved) return resolved.error;
+
       const body: Record<string, unknown> = {
-        calendarId: requireString(args, "calendarId"),
+        calendarId: resolved.calendarId,
         title: requireString(args, "title"),
         startAt: requireString(args, "startAt"),
         endAt: requireString(args, "endAt"),
@@ -375,6 +394,49 @@ async function dispatchTool(
   }
 }
 
+async function resolveCalendarId(
+  args: Record<string, unknown>,
+  request: Request,
+  origin: string,
+): Promise<{ calendarId: string } | { error: ApiCallResult }> {
+  const calendarId = typeof args.calendarId === "string" ? args.calendarId.trim() : "";
+  if (calendarId) return { calendarId };
+
+  const calendarsResult = await callApi(request, origin, "GET", "/api/v1/calendars");
+  if (calendarsResult.status !== 200 || !Array.isArray(calendarsResult.body)) {
+    return { error: calendarsResult };
+  }
+
+  const calendars = calendarsResult.body as Array<{ id?: string; name?: string }>;
+  const calendarName =
+    typeof args.calendarName === "string" ? args.calendarName.trim().toLowerCase() : "";
+
+  if (calendarName) {
+    const match = calendars.find(
+      (calendar) =>
+        typeof calendar.name === "string" && calendar.name.toLowerCase() === calendarName,
+    );
+    if (!match?.id) {
+      return {
+        error: {
+          status: 404,
+          body: {
+            error: `No calendar named "${args.calendarName}"`,
+            calendars: calendars.map((calendar) => ({ id: calendar.id, name: calendar.name })),
+          },
+        },
+      };
+    }
+    return { calendarId: match.id };
+  }
+
+  const first = calendars[0];
+  if (!first?.id) {
+    return { error: { status: 404, body: { error: "No calendars found" } } };
+  }
+  return { calendarId: first.id };
+}
+
 function requireString(args: Record<string, unknown>, key: string): string {
   const value = args[key];
   if (typeof value !== "string" || value.trim().length === 0) {
@@ -405,13 +467,18 @@ 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,
-        hint: "Pass search to filter paths, or use call_api with a /api/v1/* path.",
+        paths: pathLines.slice(0, 80),
+        pathCount: pathLines.length,
+        hint: "Pass search (e.g. calendar, events, lists) to get matching lines. Do not request the full OpenAPI dump.",
       },
     };
   }
@@ -423,8 +490,8 @@ async function getApiDocs(args: Record<string, unknown>): Promise<ApiCallResult>
     body: {
       search,
       matchCount: matches.length,
-      matches: matches.slice(0, 100),
-      hint: "Use call_api with method and path from the matches above.",
+      matches: matches.slice(0, 40),
+      hint: "Use a dedicated tool when one exists; otherwise call_api with method and path from the matches above.",
     },
   };
 }
@@ -471,14 +538,30 @@ async function callApi(
   path: string,
   body?: Record<string, unknown>,
 ): Promise<ApiCallResult> {
-  const response = await fetch(`${origin}${path}`, {
-    method,
-    headers: {
-      "Content-Type": "application/json",
-      cookie: request.headers.get("cookie") ?? "",
-    },
-    body: body !== undefined ? JSON.stringify(body) : undefined,
-  });
+  const url = `${origin}${path}`;
+  const headers: Record<string, string> = {
+    "Content-Type": "application/json",
+  };
+  const cookie = request.headers.get("cookie");
+  if (cookie) headers.cookie = cookie;
+  const authorization = request.headers.get("authorization");
+  if (authorization) headers.authorization = authorization;
+
+  let response: Response;
+  try {
+    response = await fetch(url, {
+      method,
+      headers,
+      body: body !== undefined ? JSON.stringify(body) : undefined,
+    });
+  } catch (err) {
+    const message = err instanceof Error ? err.message : "fetch failed";
+    logger.error(
+      { msg: "agent.tool.fetch_failed", method, url, error: message },
+      "agent tool internal fetch failed",
+    );
+    return { status: 502, body: { error: `Internal API unreachable: ${message}`, url } };
+  }
 
   const text = await response.text();
   let parsed: unknown = null;
@@ -490,5 +573,12 @@ async function callApi(
     }
   }
 
+  if (response.status >= 400) {
+    logger.warn(
+      { msg: "agent.tool.api_error", method, url, status: response.status, body: parsed },
+      "agent tool API error",
+    );
+  }
+
   return { status: response.status, body: parsed };
 }

src/modules/agent/tools.ts

@@ -159,11 +159,16 @@ export const AGENT_TOOLS: AgentToolDefinition[] = [
     type: "function",
     function: {
       name: "create_event",
-      description: "Create a calendar event.",
+      description:
+        "Create a calendar event. Provide calendarId, or calendarName to match by name, or omit both to use the first visible calendar.",
       parameters: {
         type: "object",
         properties: {
-          calendarId: { type: "string" },
+          calendarId: { type: "string", description: "UUID of the calendar" },
+          calendarName: {
+            type: "string",
+            description: "Calendar display name when calendarId is unknown",
+          },
           title: { type: "string" },
           startAt: { type: "string", description: "ISO 8601 start" },
           endAt: { type: "string", description: "ISO 8601 end" },
@@ -175,7 +180,7 @@ export const AGENT_TOOLS: AgentToolDefinition[] = [
             description: "Optional reminder N minutes before start",
           },
         },
-        required: ["calendarId", "title", "startAt", "endAt"],
+        required: ["title", "startAt", "endAt"],
       },
     },
   },
@@ -713,15 +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"],
       },
     },
   },
@@ -762,13 +768,15 @@ 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.
 
-When no dedicated tool fits, or you are unsure how to do something:
-1. Call get_api_docs with a relevant search term to find the right /api/v1/* endpoint.
+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.
+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. 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.
 
-Lists: resolve list ids via list_lists. To complete items, list_list_items then update_list_item with done: true.
+Lists: resolve list ids via list_lists, or pass listType to add_list_item. To complete items, list_list_items then update_list_item with done: true.
 
 Journal: per-user private entries. Valid mood ids: ${JOURNAL_MOOD_IDS}. stress is 1-10. pillsTaken is boolean.
 
@@ -776,4 +784,32 @@ Garden: care types are free text (water, fertilize, prune, etc.). Use list_garde
 
 Sharing: journal entries are not shareable. Shareable types: calendar, calendar.event, list, note, garden.plant, garden.container.
 
-Calendar: use ISO 8601 datetimes. Bang dates use YYYY-MM-DD.`;
+Calendar: use ISO 8601 datetimes with the household timezone below. Pass calendarId, or calendarName, or omit both to use the first visible calendar. Bang dates use YYYY-MM-DD.`;
+
+export function resolveHouseholdTimezone(): string {
+  return process.env.HOUSEHOLD_TIMEZONE?.trim() || process.env.TZ?.trim() || "America/Chicago";
+}
+
+export function appendAgentRuntimeContext(prompt: string, now: Date = new Date()): string {
+  const timeZone = resolveHouseholdTimezone();
+  let localNow: string;
+  try {
+    localNow = new Intl.DateTimeFormat("en-US", {
+      timeZone,
+      weekday: "long",
+      year: "numeric",
+      month: "long",
+      day: "numeric",
+      hour: "numeric",
+      minute: "2-digit",
+      hour12: true,
+      timeZoneName: "short",
+    }).format(now);
+  } catch {
+    localNow = now.toISOString();
+  }
+
+  return `${prompt.trim()}
+
+Current time: ${localNow} (${timeZone}). ISO now: ${now.toISOString()}. Resolve relative dates from this clock.`;
+}

tests/unit/agent-chat.test.ts

@@ -83,6 +83,36 @@ describe("runAgentChat", () => {
     assert.equal(result.message.role, "assistant");
     assert.ok(result.message.content.length > 0);
   });
+
+  it("appends runtime clock context to the system prompt", async () => {
+    const original = process.env.HOUSEHOLD_TIMEZONE;
+    process.env.HOUSEHOLD_TIMEZONE = "America/Chicago";
+
+    let systemContent = "";
+    const result = await runAgentChat({
+      messages: [{ role: "user", content: "hello" }],
+      request: new Request("http://localhost:3000/api/agent/chat"),
+      systemPrompt: "You are a pirate.",
+      llm: {
+        async chatCompletion(request) {
+          const system = request.messages.find((message) => message.role === "system");
+          systemContent = typeof system?.content === "string" ? system.content : "";
+          return {
+            message: { role: "assistant", content: "Ahoy" },
+            finishReason: "stop",
+          };
+        },
+      },
+    });
+
+    assert.equal(result.message.content, "Ahoy");
+    assert.match(systemContent, /^You are a pirate\./);
+    assert.match(systemContent, /Current time:/);
+    assert.match(systemContent, /America\/Chicago/);
+
+    if (original === undefined) delete process.env.HOUSEHOLD_TIMEZONE;
+    else process.env.HOUSEHOLD_TIMEZONE = original;
+  });
 });
 
 it("passes a model override to the OpenAI-compatible client", async () => {

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/);
+  });
+});

tests/unit/agent-tools-runtime.test.ts

@@ -0,0 +1,171 @@
+import assert from "node:assert/strict";
+import { describe, it } from "node:test";
+import { appendAgentRuntimeContext, resolveHouseholdTimezone } from "../../src/modules/agent/tools";
+import {
+  createApiToolExecutor,
+  resolveInternalApiBase,
+} from "../../src/modules/agent/tool-executor";
+
+describe("appendAgentRuntimeContext", () => {
+  it("appends current time and timezone to the prompt", () => {
+    const original = process.env.HOUSEHOLD_TIMEZONE;
+    process.env.HOUSEHOLD_TIMEZONE = "America/Chicago";
+
+    const now = new Date("2026-07-09T14:30:00.000Z");
+    const result = appendAgentRuntimeContext("Be helpful.", now);
+
+    assert.match(result, /^Be helpful\./);
+    assert.match(result, /Current time:/);
+    assert.match(result, /America\/Chicago/);
+    assert.match(result, /2026-07-09T14:30:00\.000Z/);
+    assert.match(result, /Resolve relative dates from this clock/);
+
+    if (original === undefined) delete process.env.HOUSEHOLD_TIMEZONE;
+    else process.env.HOUSEHOLD_TIMEZONE = original;
+  });
+});
+
+describe("resolveHouseholdTimezone", () => {
+  it("prefers HOUSEHOLD_TIMEZONE over TZ", () => {
+    const originalHousehold = process.env.HOUSEHOLD_TIMEZONE;
+    const originalTz = process.env.TZ;
+    process.env.HOUSEHOLD_TIMEZONE = "America/New_York";
+    process.env.TZ = "UTC";
+
+    assert.equal(resolveHouseholdTimezone(), "America/New_York");
+
+    if (originalHousehold === undefined) delete process.env.HOUSEHOLD_TIMEZONE;
+    else process.env.HOUSEHOLD_TIMEZONE = originalHousehold;
+    if (originalTz === undefined) delete process.env.TZ;
+    else process.env.TZ = originalTz;
+  });
+});
+
+describe("resolveInternalApiBase", () => {
+  it("uses loopback instead of the public request origin", () => {
+    const original = process.env.INTERNAL_API_BASE_URL;
+    const originalPort = process.env.PORT;
+    delete process.env.INTERNAL_API_BASE_URL;
+    process.env.PORT = "3000";
+
+    const base = resolveInternalApiBase(new Request("https://fam.ginnoir.com/api/agent/chat"));
+    assert.equal(base, "http://127.0.0.1:3000");
+
+    if (original === undefined) delete process.env.INTERNAL_API_BASE_URL;
+    else process.env.INTERNAL_API_BASE_URL = original;
+    if (originalPort === undefined) delete process.env.PORT;
+    else process.env.PORT = originalPort;
+  });
+
+  it("honors INTERNAL_API_BASE_URL when set", () => {
+    const original = process.env.INTERNAL_API_BASE_URL;
+    process.env.INTERNAL_API_BASE_URL = "http://127.0.0.1:3010/";
+
+    const base = resolveInternalApiBase(new Request("https://fam.ginnoir.com/api/agent/chat"));
+    assert.equal(base, "http://127.0.0.1:3010");
+
+    if (original === undefined) delete process.env.INTERNAL_API_BASE_URL;
+    else process.env.INTERNAL_API_BASE_URL = original;
+  });
+});
+
+describe("create_event calendar resolution", () => {
+  it("uses the first calendar when calendarId and calendarName are omitted", async () => {
+    const originalFetch = globalThis.fetch;
+    const posts: Array<{ path: string; body: unknown }> = [];
+
+    globalThis.fetch = (async (input: RequestInfo | URL, init?: RequestInit) => {
+      const url = String(input);
+      if (url.includes("/api/v1/calendars") && (!init?.method || init.method === "GET")) {
+        return Response.json([
+          { id: "cal-1", name: "Family" },
+          { id: "cal-2", name: "Work" },
+        ]);
+      }
+      if (url.includes("/api/v1/events") && init?.method === "POST") {
+        const body = JSON.parse(String(init.body));
+        posts.push({ path: url, body });
+        return Response.json({ id: "evt-1", ...body }, { status: 201 });
+      }
+      return new Response("not found", { status: 404 });
+    }) as typeof fetch;
+
+    const execute = createApiToolExecutor(
+      new Request("https://fam.ginnoir.com/api/agent/chat", {
+        headers: { cookie: "authjs.session-token=test" },
+      }),
+    );
+    const result = JSON.parse(
+      await execute(
+        "create_event",
+        JSON.stringify({
+          title: "Dentist",
+          startAt: "2026-07-10T15:00:00.000Z",
+          endAt: "2026-07-10T16:00:00.000Z",
+        }),
+      ),
+    ) as { status: number; body: { calendarId?: string } };
+
+    assert.equal(result.status, 201);
+    assert.equal(result.body.calendarId, "cal-1");
+    assert.equal(posts.length, 1);
+    assert.match(posts[0]!.path, /^http:\/\/127\.0\.0\.1:3000\/api\/v1\/events/);
+
+    globalThis.fetch = originalFetch;
+  });
+
+  it("matches calendarName case-insensitively", async () => {
+    const originalFetch = globalThis.fetch;
+
+    globalThis.fetch = (async (input: RequestInfo | URL, init?: RequestInit) => {
+      const url = String(input);
+      if (url.includes("/api/v1/calendars") && (!init?.method || init.method === "GET")) {
+        return Response.json([
+          { id: "cal-1", name: "Family" },
+          { id: "cal-2", name: "Work" },
+        ]);
+      }
+      if (url.includes("/api/v1/events") && init?.method === "POST") {
+        const body = JSON.parse(String(init.body));
+        return Response.json({ id: "evt-1", ...body }, { status: 201 });
+      }
+      return new Response("not found", { status: 404 });
+    }) as typeof fetch;
+
+    const execute = createApiToolExecutor(new Request("http://localhost:3000/api/agent/chat"));
+    const result = JSON.parse(
+      await execute(
+        "create_event",
+        JSON.stringify({
+          calendarName: "work",
+          title: "Standup",
+          startAt: "2026-07-10T15:00:00.000Z",
+          endAt: "2026-07-10T15:30:00.000Z",
+        }),
+      ),
+    ) as { status: number; body: { calendarId?: string } };
+
+    assert.equal(result.status, 201);
+    assert.equal(result.body.calendarId, "cal-2");
+
+    globalThis.fetch = originalFetch;
+  });
+
+  it("returns a clear error when the internal API is unreachable", async () => {
+    const originalFetch = globalThis.fetch;
+    globalThis.fetch = (async () => {
+      throw new TypeError("fetch failed");
+    }) as typeof fetch;
+
+    const execute = createApiToolExecutor(new Request("https://fam.ginnoir.com/api/agent/chat"));
+    const result = JSON.parse(await execute("list_calendars", "{}")) as {
+      status: number;
+      body: { error?: string };
+    };
+
+    assert.equal(result.status, 502);
+    assert.match(String(result.body.error), /unreachable/i);
+
+    globalThis.fetch = originalFetch;
+  });
+});