diff --git a/src/agents/pi-tool-definition-adapter.ts b/src/agents/pi-tool-definition-adapter.ts
index 9f4451625..95a261d6c 100644
--- a/src/agents/pi-tool-definition-adapter.ts
+++ b/src/agents/pi-tool-definition-adapter.ts
@@ -21,6 +21,67 @@ function describeToolExecutionError(err: unknown): {
   return { message: String(err) };
 }
 
+function asScalar(value: unknown): string | undefined {
+  if (typeof value === "string") {
+    const trimmed = value.trim();
+    return trimmed ? trimmed : undefined;
+  }
+  if (typeof value === "number" && Number.isFinite(value)) return String(value);
+  if (typeof value === "bigint") return String(value);
+  return undefined;
+}
+
+function summarizeList(value: unknown): string | undefined {
+  if (!Array.isArray(value)) return undefined;
+  const items = value.map(asScalar).filter((entry): entry is string => Boolean(entry));
+  if (items.length === 0) return undefined;
+  const sample = items.slice(0, 3).join(", ");
+  const suffix = items.length > 3 ? ` (+${items.length - 3})` : "";
+  return `${sample}${suffix}`;
+}
+
+function looksLikeMemberTarget(value: string): boolean {
+  return /^user:/i.test(value) || value.startsWith("@") || /^<@!?/.test(value);
+}
+
+function describeMessageToolContext(params: Record<string, unknown>): string | undefined {
+  const action = asScalar(params.action);
+  const channel = asScalar(params.channel);
+  const accountId = asScalar(params.accountId);
+  const guildId = asScalar(params.guildId);
+  const channelId = asScalar(params.channelId);
+  const threadId = asScalar(params.threadId);
+  const messageId = asScalar(params.messageId);
+  const userId = asScalar(params.userId) ?? asScalar(params.authorId) ?? asScalar(params.participant);
+  const target =
+    asScalar(params.target) ??
+    asScalar(params.to) ??
+    summarizeList(params.targets) ??
+    summarizeList(params.target);
+
+  const member =
+    userId ?? (target && looksLikeMemberTarget(target) ? target : undefined) ?? undefined;
+  const pairs: string[] = [];
+  if (action) pairs.push(`action=${action}`);
+  if (channel) pairs.push(`channel=${channel}`);
+  if (accountId) pairs.push(`accountId=${accountId}`);
+  if (member) {
+    pairs.push(`member=${member}`);
+  } else if (target) {
+    pairs.push(`target=${target}`);
+  }
+  if (guildId) pairs.push(`guildId=${guildId}`);
+  if (channelId) pairs.push(`channelId=${channelId}`);
+  if (threadId) pairs.push(`threadId=${threadId}`);
+  if (messageId) pairs.push(`messageId=${messageId}`);
+  return pairs.length > 0 ? pairs.join(" ") : undefined;
+}
+
+function describeToolContext(toolName: string, params: Record<string, unknown>): string | undefined {
+  if (toolName === "message") return describeMessageToolContext(params);
+  return undefined;
+}
+
 export function toToolDefinitions(tools: AnyAgentTool[]): ToolDefinition[] {
   return tools.map((tool) => {
     const name = tool.name || "tool";
@@ -52,7 +113,9 @@ export function toToolDefinitions(tools: AnyAgentTool[]): ToolDefinition[] {
           if (described.stack && described.stack !== described.message) {
             logDebug(`tools: ${tool.name} failed stack:\n${described.stack}`);
           }
-          logError(`[tools] ${tool.name} failed: ${described.message}`);
+          const context = describeToolContext(tool.name, params);
+          const suffix = context ? ` (${context})` : "";
+          logError(`tools: ${tool.name} failed: ${described.message}${suffix}`);
           return jsonResult({
             status: "error",
             tool: tool.name,
diff --git a/src/cli/gateway-cli/run.ts b/src/cli/gateway-cli/run.ts
index b8f512b4b..5c83aa2ff 100644
--- a/src/cli/gateway-cli/run.ts
+++ b/src/cli/gateway-cli/run.ts
@@ -15,7 +15,11 @@ import { setGatewayWsLogStyle } from "../../gateway/ws-logging.js";
 import { setVerbose } from "../../globals.js";
 import { GatewayLockError } from "../../infra/gateway-lock.js";
 import { formatPortDiagnostics, inspectPortUsage } from "../../infra/ports.js";
-import { createSubsystemLogger, setConsoleSubsystemFilter } from "../../logging.js";
+import {
+  createSubsystemLogger,
+  setConsoleSubsystemFilter,
+  setConsoleTimestampPrefix,
+} from "../../logging.js";
 import { defaultRuntime } from "../../runtime.js";
 import { forceFreePortAndWait } from "../ports.js";
 import { ensureDevGatewayConfig } from "./dev.js";
@@ -59,6 +63,7 @@ async function runGatewayCommand(opts: GatewayRunOpts) {
     return;
   }
 
+  setConsoleTimestampPrefix(true);
   setVerbose(Boolean(opts.verbose));
   if (opts.claudeCliLogs) {
     setConsoleSubsystemFilter(["agent/claude-cli"]);
diff --git a/src/logging/console-capture.test.ts b/src/logging/console-capture.test.ts
index 623587604..fe10a6da4 100644
--- a/src/logging/console-capture.test.ts
+++ b/src/logging/console-capture.test.ts
@@ -8,6 +8,7 @@ import {
   enableConsoleCapture,
   resetLogger,
   routeLogsToStderr,
+  setConsoleTimestampPrefix,
   setLoggerOverride,
 } from "../logging.js";
 import { loggingState } from "./state.js";
@@ -34,6 +35,7 @@ beforeEach(() => {
   };
   loggingState.consolePatched = false;
   loggingState.forceConsoleToStderr = false;
+  loggingState.consoleTimestampPrefix = false;
   loggingState.rawConsole = null;
   resetLogger();
 });
@@ -47,6 +49,7 @@ afterEach(() => {
   console.trace = snapshot.trace;
   loggingState.consolePatched = false;
   loggingState.forceConsoleToStderr = false;
+  loggingState.consoleTimestampPrefix = false;
   loggingState.rawConsole = null;
   resetLogger();
   setLoggerOverride(null);
@@ -72,6 +75,43 @@ describe("enableConsoleCapture", () => {
     enableConsoleCapture();
     expect(() => console.log("hello")).not.toThrow();
   });
+
+  it("prefixes console output with timestamps when enabled", () => {
+    setLoggerOverride({ level: "info", file: tempLogPath() });
+    const now = new Date("2026-01-17T18:01:02.000Z");
+    vi.useFakeTimers();
+    vi.setSystemTime(now);
+    const warn = vi.fn();
+    console.warn = warn;
+    setConsoleTimestampPrefix(true);
+    enableConsoleCapture();
+    console.warn("[EventQueue] Slow listener detected");
+    expect(warn).toHaveBeenCalledTimes(1);
+    const firstArg = String(warn.mock.calls[0]?.[0] ?? "");
+    expect(firstArg.startsWith("2026-01-17T18:01:02.000Z [EventQueue]")).toBe(true);
+    vi.useRealTimers();
+  });
+
+  it("does not double-prefix timestamps", () => {
+    setLoggerOverride({ level: "info", file: tempLogPath() });
+    const warn = vi.fn();
+    console.warn = warn;
+    setConsoleTimestampPrefix(true);
+    enableConsoleCapture();
+    console.warn("12:34:56 [exec] hello");
+    expect(warn).toHaveBeenCalledWith("12:34:56 [exec] hello");
+  });
+
+  it("leaves JSON output unchanged when timestamp prefix is enabled", () => {
+    setLoggerOverride({ level: "info", file: tempLogPath() });
+    const log = vi.fn();
+    console.log = log;
+    setConsoleTimestampPrefix(true);
+    enableConsoleCapture();
+    const payload = JSON.stringify({ ok: true });
+    console.log(payload);
+    expect(log).toHaveBeenCalledWith(payload);
+  });
 });
 
 function tempLogPath() {
diff --git a/src/logging/console.ts b/src/logging/console.ts
index 88adbb1b1..013ec4bfb 100644
--- a/src/logging/console.ts
+++ b/src/logging/console.ts
@@ -67,6 +67,10 @@ export function setConsoleSubsystemFilter(filters?: string[] | null): void {
   loggingState.consoleSubsystemFilter = normalized.length > 0 ? normalized : null;
 }
 
+export function setConsoleTimestampPrefix(enabled: boolean): void {
+  loggingState.consoleTimestampPrefix = enabled;
+}
+
 export function shouldLogSubsystemToConsole(subsystem: string): boolean {
   const filter = loggingState.consoleSubsystemFilter;
   if (!filter || filter.length === 0) {
@@ -93,6 +97,33 @@ function isEpipeError(err: unknown): boolean {
   return code === "EPIPE" || code === "EIO";
 }
 
+function formatConsoleTimestamp(style: ConsoleStyle): string {
+  const now = new Date().toISOString();
+  if (style === "pretty") return now.slice(11, 19);
+  return now;
+}
+
+function hasTimestampPrefix(value: string): boolean {
+  return /^(?:\d{2}:\d{2}:\d{2}|\d{4}-\d{2}-\d{2}T\d{2}:\d{2}:\d{2}(?:\.\d+)?Z?)/.test(
+    value,
+  );
+}
+
+function isJsonPayload(value: string): boolean {
+  const trimmed = value.trim();
+  if (!trimmed.startsWith("{") && !trimmed.startsWith("[")) return false;
+  try {
+    JSON.parse(trimmed);
+    return true;
+  } catch {
+    return false;
+  }
+}
+
+function stripAnsi(value: string): string {
+  return value.replace(/\u001b\[[0-9;]*m/g, "");
+}
+
 /**
  * Route console.* calls through file logging while still emitting to stdout/stderr.
  * This keeps user-facing output unchanged but guarantees every console call is captured in log files.
@@ -123,6 +154,15 @@ export function enableConsoleCapture(): void {
     (...args: unknown[]) => {
       const formatted = util.format(...args);
       if (shouldSuppressConsoleMessage(formatted)) return;
+      const trimmed = stripAnsi(formatted).trimStart();
+      const shouldPrefixTimestamp =
+        loggingState.consoleTimestampPrefix &&
+        trimmed.length > 0 &&
+        !hasTimestampPrefix(trimmed) &&
+        !isJsonPayload(trimmed);
+      const timestamp = shouldPrefixTimestamp
+        ? formatConsoleTimestamp(getConsoleSettings().style)
+        : "";
       try {
         // Map console levels to file logger
         if (level === "trace") {
@@ -144,14 +184,27 @@ export function enableConsoleCapture(): void {
       if (loggingState.forceConsoleToStderr) {
         // in RPC/JSON mode, keep stdout clean
         try {
-          process.stderr.write(`${formatted}\n`);
+          const line = timestamp ? `${timestamp} ${formatted}` : formatted;
+          process.stderr.write(`${line}\n`);
         } catch (err) {
           if (isEpipeError(err)) return;
           throw err;
         }
       } else {
         try {
-          orig.apply(console, args as []);
+          if (!timestamp) {
+            orig.apply(console, args as []);
+            return;
+          }
+          if (args.length === 0) {
+            orig.call(console, timestamp);
+            return;
+          }
+          if (typeof args[0] === "string") {
+            orig.call(console, `${timestamp} ${args[0]}`, ...args.slice(1));
+            return;
+          }
+          orig.call(console, timestamp, ...args);
         } catch (err) {
           if (isEpipeError(err)) return;
           throw err;
diff --git a/src/logging/state.ts b/src/logging/state.ts
index 0481430b1..77badf8ea 100644
--- a/src/logging/state.ts
+++ b/src/logging/state.ts
@@ -5,6 +5,7 @@ export const loggingState = {
   overrideSettings: null as unknown,
   consolePatched: false,
   forceConsoleToStderr: false,
+  consoleTimestampPrefix: false,
   consoleSubsystemFilter: null as string[] | null,
   rawConsole: null as {
     log: typeof console.log;