diff --git a/src/agents/agent-command.ts b/src/agents/agent-command.ts
index 5db40b13a27..e2ef701e030 100644
--- a/src/agents/agent-command.ts
+++ b/src/agents/agent-command.ts
@@ -492,6 +492,7 @@ function runAgentAttempt(params: {
     sessionKey: params.sessionKey,
     agentId: params.sessionAgentId,
     trigger: "user",
+    runContext: { sessionTarget: "main" },
     messageChannel: params.messageChannel,
     agentAccountId: params.runContext.accountId,
     messageTo: params.opts.replyTo ?? params.opts.to,
diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index d785218f819..1cc68f131b0 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -2549,6 +2549,13 @@ export async function runEmbeddedAttempt(
         sessionKey: sandboxSessionKey,
         sessionId: params.sessionId,
         agentId: sessionAgentId,
+        runContext: {
+          sessionTarget:
+            params.runContext?.sessionTarget ??
+            (params.trigger === "cron" ? "isolated" : sandboxSessionKey ? "main" : undefined),
+          cronJobId: params.runContext?.cronJobId,
+          maintenanceScope: params.runContext?.maintenanceScope,
+        },
       });
 
       const {
diff --git a/src/agents/pi-embedded-runner/run/params.ts b/src/agents/pi-embedded-runner/run/params.ts
index f59bb8f27b5..2e33399976f 100644
--- a/src/agents/pi-embedded-runner/run/params.ts
+++ b/src/agents/pi-embedded-runner/run/params.ts
@@ -20,6 +20,12 @@ export type ClientToolDefinition = {
   };
 };
 
+export type RunEmbeddedPiAgentContext = {
+  sessionTarget?: "main" | "isolated";
+  cronJobId?: string;
+  maintenanceScope?: string;
+};
+
 export type RunEmbeddedPiAgentParams = {
   sessionId: string;
   sessionKey?: string;
@@ -119,6 +125,7 @@ export type RunEmbeddedPiAgentParams = {
   streamParams?: AgentStreamParams;
   ownerNumbers?: string[];
   enforceFinalTag?: boolean;
+  runContext?: RunEmbeddedPiAgentContext;
   /**
    * Allow a single run attempt even when all auth profiles are in cooldown,
    * but only for inferred transient cooldowns like `rate_limit` or `overloaded`.
diff --git a/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts b/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts
index 911b124113a..4299d2711c8 100644
--- a/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.lifecycle.test.ts
@@ -9,13 +9,22 @@ vi.mock("../infra/agent-events.js", () => ({
 
 function createContext(
   lastAssistant: unknown,
-  overrides?: { onAgentEvent?: (event: unknown) => void },
+  overrides?: {
+    onAgentEvent?: (event: unknown) => void;
+    sessionKey?: string;
+    runContext?: {
+      sessionTarget?: "main" | "isolated";
+      cronJobId?: string;
+      maintenanceScope?: string;
+    };
+  },
 ): EmbeddedPiSubscribeContext {
   return {
     params: {
       runId: "run-1",
       config: {},
-      sessionKey: "agent:main:main",
+      sessionKey: overrides?.sessionKey ?? "agent:main:main",
+      runContext: overrides?.runContext,
       onAgentEvent: overrides?.onAgentEvent,
     },
     state: {
@@ -60,6 +69,8 @@ describe("handleAgentEnd", () => {
       runId: "run-1",
       error: "connection refused",
       rawErrorPreview: "connection refused",
+      sessionTarget: "main",
+      sessionKey: "agent:main:main",
     });
     expect(onAgentEvent).toHaveBeenCalledWith({
       stream: "lifecycle",
@@ -157,4 +168,38 @@ describe("handleAgentEnd", () => {
     expect(ctx.log.warn).not.toHaveBeenCalled();
     expect(ctx.log.debug).toHaveBeenCalledWith("embedded run agent end: runId=run-1 isError=false");
   });
+
+  it("includes explicit provenance metadata in error logs when provided by the runtime", () => {
+    const ctx = createContext(
+      {
+        role: "assistant",
+        stopReason: "error",
+        errorMessage: "provider overloaded",
+        content: [{ type: "text", text: "" }],
+      },
+      {
+        sessionKey: "agent:main:cron:job-1",
+        runContext: {
+          sessionTarget: "isolated",
+          cronJobId: "job-1",
+          maintenanceScope: "watchdog",
+        },
+      },
+    );
+
+    handleAgentEnd(ctx);
+
+    expect(vi.mocked(ctx.log.warn).mock.calls[0]?.[1]).toMatchObject({
+      sessionTarget: "isolated",
+      sessionKey: "agent:main:cron:job-1",
+      cronJobId: "job-1",
+      maintenanceScope: "watchdog",
+      runContext: {
+        sessionTarget: "isolated",
+        sessionKey: "agent:main:cron:job-1",
+        cronJobId: "job-1",
+        maintenanceScope: "watchdog",
+      },
+    });
+  });
 });
diff --git a/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts b/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts
index 973de1ebefc..591f466e7be 100644
--- a/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.lifecycle.ts
@@ -1,5 +1,6 @@
 import { emitAgentEvent } from "../infra/agent-events.js";
 import { createInlineCodeState } from "../markdown/code-spans.js";
+import { isCronSessionKey } from "../sessions/session-key-utils.js";
 import {
   buildApiErrorObservationFields,
   buildTextObservationFields,
@@ -33,6 +34,14 @@ export function handleAgentStart(ctx: EmbeddedPiSubscribeContext) {
 export function handleAgentEnd(ctx: EmbeddedPiSubscribeContext) {
   const lastAssistant = ctx.state.lastAssistant;
   const isError = isAssistantMessage(lastAssistant) && lastAssistant.stopReason === "error";
+  const runContext = ctx.params.runContext ?? {};
+  const sessionTarget =
+    runContext.sessionTarget ??
+    (isCronSessionKey(ctx.params.sessionKey)
+      ? "isolated"
+      : ctx.params.sessionKey
+        ? "main"
+        : undefined);
 
   if (isError && lastAssistant) {
     const friendlyError = formatAssistantErrorText(lastAssistant, {
@@ -59,6 +68,16 @@ export function handleAgentEnd(ctx: EmbeddedPiSubscribeContext) {
       failoverReason,
       model: lastAssistant.model,
       provider: lastAssistant.provider,
+      sessionTarget,
+      sessionKey: ctx.params.sessionKey,
+      cronJobId: runContext.cronJobId,
+      maintenanceScope: runContext.maintenanceScope,
+      runContext: {
+        sessionTarget,
+        sessionKey: ctx.params.sessionKey,
+        cronJobId: runContext.cronJobId,
+        maintenanceScope: runContext.maintenanceScope,
+      },
       ...observedError,
       consoleMessage: `embedded run agent end: runId=${safeRunId} isError=true model=${safeModel} provider=${safeProvider} error=${safeErrorText}`,
     });
diff --git a/src/agents/pi-embedded-subscribe.types.ts b/src/agents/pi-embedded-subscribe.types.ts
index bbb2d552d73..8cef20440e3 100644
--- a/src/agents/pi-embedded-subscribe.types.ts
+++ b/src/agents/pi-embedded-subscribe.types.ts
@@ -36,6 +36,11 @@ export type SubscribeEmbeddedPiSessionParams = {
   sessionId?: string;
   /** Agent identity for hook context — resolved from session config in attempt.ts. */
   agentId?: string;
+  runContext?: {
+    sessionTarget?: "main" | "isolated";
+    cronJobId?: string;
+    maintenanceScope?: string;
+  };
 };
 
 export type { BlockReplyChunking } from "./pi-embedded-block-chunker.js";
diff --git a/src/auto-reply/reply/agent-runner-execution.ts b/src/auto-reply/reply/agent-runner-execution.ts
index c25342e4a28..9a84c852b6b 100644
--- a/src/auto-reply/reply/agent-runner-execution.ts
+++ b/src/auto-reply/reply/agent-runner-execution.ts
@@ -327,6 +327,7 @@ export async function runAgentTurnWithFallback(params: {
                 ...embeddedContext,
                 allowGatewaySubagentBinding: true,
                 trigger: params.isHeartbeat ? "heartbeat" : "user",
+                runContext: { sessionTarget: "main" },
                 groupId: resolveGroupSessionKey(params.sessionCtx)?.id,
                 groupChannel:
                   params.sessionCtx.GroupChannel?.trim() ?? params.sessionCtx.GroupSubject?.trim(),
diff --git a/src/auto-reply/reply/agent-runner-memory.ts b/src/auto-reply/reply/agent-runner-memory.ts
index 267326a7e20..408c820a59a 100644
--- a/src/auto-reply/reply/agent-runner-memory.ts
+++ b/src/auto-reply/reply/agent-runner-memory.ts
@@ -496,6 +496,7 @@ export async function runMemoryFlushIfNeeded(params: {
           ...runBaseParams,
           allowGatewaySubagentBinding: true,
           trigger: "memory",
+          runContext: { maintenanceScope: "memory-flush" },
           memoryFlushWritePath,
           prompt: resolveMemoryFlushPromptForRun({
             prompt: memoryFlushSettings.prompt,
diff --git a/src/auto-reply/reply/followup-runner.ts b/src/auto-reply/reply/followup-runner.ts
index 2fd21607095..a6e4165a2dd 100644
--- a/src/auto-reply/reply/followup-runner.ts
+++ b/src/auto-reply/reply/followup-runner.ts
@@ -179,6 +179,7 @@ export function createFollowupRunner(params: {
                 sessionKey: queued.run.sessionKey,
                 agentId: queued.run.agentId,
                 trigger: "user",
+                runContext: { sessionTarget: "main" },
                 messageChannel: queued.originatingChannel ?? undefined,
                 messageProvider: queued.run.messageProvider,
                 agentAccountId: queued.run.agentAccountId,
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index 1a122f56864..0b4ebe7bf4b 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -659,6 +659,10 @@ export async function runCronIsolatedAgentTurn(params: {
             bootstrapContextMode: agentPayload?.lightContext ? "lightweight" : undefined,
             bootstrapContextRunKind: "cron",
             runId: cronSession.sessionEntry.sessionId,
+            runContext: {
+              sessionTarget: "isolated",
+              cronJobId: params.job.id,
+            },
             requireExplicitMessageTarget: toolPolicy.requireExplicitMessageTarget,
             disableMessageTool: toolPolicy.disableMessageTool,
             allowTransientCooldownProbe: runOptions?.allowTransientCooldownProbe,