diff --git a/src/agents/pi-embedded-runner/compact.queued.ts b/src/agents/pi-embedded-runner/compact.queued.ts
index 496112256b1..267d48fba7c 100644
--- a/src/agents/pi-embedded-runner/compact.queued.ts
+++ b/src/agents/pi-embedded-runner/compact.queued.ts
@@ -235,6 +235,7 @@ export async function compactEmbeddedPiSession(
           }
           await runContextEngineMaintenance({
             contextEngine,
+            sessionAgentId: agentIds.sessionAgentId,
             sessionId: postCompactionSessionId,
             sessionKey: params.sessionKey,
             sessionFile: postCompactionSessionFile,
diff --git a/src/agents/pi-embedded-runner/context-engine-maintenance.ts b/src/agents/pi-embedded-runner/context-engine-maintenance.ts
index fe79ca47e47..1a3532c473a 100644
--- a/src/agents/pi-embedded-runner/context-engine-maintenance.ts
+++ b/src/agents/pi-embedded-runner/context-engine-maintenance.ts
@@ -43,6 +43,7 @@ const DEFERRED_TURN_MAINTENANCE_ABORT_STATE_KEY = Symbol.for(
 );
 type DeferredTurnMaintenanceScheduleParams = {
   contextEngine: ContextEngine;
+  sessionAgentId?: string;
   sessionId: string;
   sessionKey: string;
   sessionFile: string;
@@ -273,6 +274,7 @@ function promoteTurnMaintenanceTaskVisibility(params: {
  * context-engine runtime context payload.
  */
 export function buildContextEngineMaintenanceRuntimeContext(params: {
+  sessionAgentId?: string;
   sessionId: string;
   sessionKey?: string;
   sessionFile: string;
@@ -305,6 +307,7 @@ export function buildContextEngineMaintenanceRuntimeContext(params: {
       const rewriteTranscriptEntriesInFile = async () =>
         await rewriteTranscriptEntriesInSqliteTranscript({
           transcriptPath: params.sessionFile,
+          agentId: params.sessionAgentId,
           sessionId: params.sessionId,
           sessionKey: params.sessionKey,
           config: params.config,
@@ -324,6 +327,7 @@ export function buildContextEngineMaintenanceRuntimeContext(params: {
 
 async function executeContextEngineMaintenance(params: {
   contextEngine: ContextEngine;
+  sessionAgentId?: string;
   sessionId: string;
   sessionKey?: string;
   sessionFile: string;
@@ -342,6 +346,7 @@ async function executeContextEngineMaintenance(params: {
     sessionKey: params.sessionKey,
     sessionFile: params.sessionFile,
     runtimeContext: buildContextEngineMaintenanceRuntimeContext({
+      sessionAgentId: params.sessionAgentId,
       sessionId: params.sessionId,
       sessionKey: params.sessionKey,
       sessionFile: params.sessionFile,
@@ -367,6 +372,7 @@ async function executeContextEngineMaintenance(params: {
 
 async function runDeferredTurnMaintenanceWorker(params: {
   contextEngine: ContextEngine;
+  sessionAgentId?: string;
   sessionId: string;
   sessionKey: string;
   sessionFile: string;
@@ -447,6 +453,7 @@ async function runDeferredTurnMaintenanceWorker(params: {
 
     const result = await executeContextEngineMaintenance({
       contextEngine: params.contextEngine,
+      sessionAgentId: params.sessionAgentId,
       sessionId: params.sessionId,
       sessionKey: params.sessionKey,
       sessionFile: params.sessionFile,
@@ -572,6 +579,7 @@ function scheduleDeferredTurnMaintenance(params: DeferredTurnMaintenanceSchedule
     runPromise = enqueueCommandInLane(resolveDeferredTurnMaintenanceLane(sessionKey), async () =>
       runDeferredTurnMaintenanceWorker({
         contextEngine: params.contextEngine,
+        sessionAgentId: params.sessionAgentId,
         sessionId: params.sessionId,
         sessionKey,
         sessionFile: params.sessionFile,
@@ -628,6 +636,7 @@ function scheduleDeferredTurnMaintenance(params: DeferredTurnMaintenanceSchedule
  */
 export async function runContextEngineMaintenance(params: {
   contextEngine?: ContextEngine;
+  sessionAgentId?: string;
   sessionId: string;
   sessionKey?: string;
   sessionFile: string;
@@ -652,6 +661,7 @@ export async function runContextEngineMaintenance(params: {
     try {
       scheduleDeferredTurnMaintenance({
         contextEngine: params.contextEngine,
+        sessionAgentId: params.sessionAgentId,
         sessionId: params.sessionId,
         sessionKey: params.sessionKey ?? params.sessionId,
         sessionFile: params.sessionFile,
@@ -669,6 +679,7 @@ export async function runContextEngineMaintenance(params: {
   try {
     return await executeContextEngineMaintenance({
       contextEngine: params.contextEngine,
+      sessionAgentId: params.sessionAgentId,
       sessionId: params.sessionId,
       sessionKey: params.sessionKey,
       sessionFile: params.sessionFile,
diff --git a/src/agents/pi-embedded-runner/run.ts b/src/agents/pi-embedded-runner/run.ts
index df3bd227030..08831cd9bf5 100644
--- a/src/agents/pi-embedded-runner/run.ts
+++ b/src/agents/pi-embedded-runner/run.ts
@@ -1857,6 +1857,7 @@ export async function runEmbeddedPiAgent(
                   adoptCompactionTranscript(compactResult);
                   await runContextEngineMaintenance({
                     contextEngine,
+                    sessionAgentId,
                     sessionId: activeSessionId,
                     sessionKey: params.sessionKey,
                     sessionFile: activeSessionFile,
@@ -1895,6 +1896,7 @@ export async function runEmbeddedPiAgent(
                       cfg: params.config,
                       agentId: sessionAgentId,
                     }),
+                    agentId: sessionAgentId,
                     sessionId: activeSessionId,
                     sessionKey: params.sessionKey,
                     config: params.config,
@@ -1957,6 +1959,7 @@ export async function runEmbeddedPiAgent(
                   sessionFile: activeSessionFile,
                   contextWindowTokens,
                   maxCharsOverride: toolResultMaxChars,
+                  agentId: sessionAgentId,
                   sessionId: activeSessionId,
                   sessionKey: params.sessionKey,
                   config: params.config,
diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index b90f5f74a46..4a9af641e77 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -1466,6 +1466,7 @@ export async function runEmbeddedAttempt(
         runMaintenance: async (contextParams) =>
           await runContextEngineMaintenance({
             contextEngine: contextParams.contextEngine as never,
+            sessionAgentId,
             sessionId: contextParams.sessionId,
             sessionKey: contextParams.sessionKey,
             sessionFile: contextParams.sessionFile,
@@ -2593,6 +2594,7 @@ export async function runEmbeddedAttempt(
             sessionManager: activeSessionManager,
             contextWindowTokens: contextTokenBudget,
             maxCharsOverride: toolResultMaxChars,
+            agentId: sessionAgentId,
             sessionFile: params.sessionFile,
             sessionId: params.sessionId,
             sessionKey: params.sessionKey,
@@ -3135,6 +3137,7 @@ export async function runEmbeddedAttempt(
               sessionManager,
               contextWindowTokens: contextTokenBudget,
               maxCharsOverride: toolResultMaxChars,
+              agentId: sessionAgentId,
               sessionFile: params.sessionFile,
               sessionId: params.sessionId,
               sessionKey: params.sessionKey,
@@ -3463,6 +3466,7 @@ export async function runEmbeddedAttempt(
             runMaintenance: async (contextParams) =>
               await runContextEngineMaintenance({
                 contextEngine: contextParams.contextEngine as never,
+                sessionAgentId,
                 sessionId: contextParams.sessionId,
                 sessionKey: contextParams.sessionKey,
                 sessionFile: contextParams.sessionFile,
diff --git a/src/agents/pi-embedded-runner/tool-result-truncation.ts b/src/agents/pi-embedded-runner/tool-result-truncation.ts
index 8038728695b..b7646dc5480 100644
--- a/src/agents/pi-embedded-runner/tool-result-truncation.ts
+++ b/src/agents/pi-embedded-runner/tool-result-truncation.ts
@@ -617,6 +617,7 @@ function truncateOversizedToolResultsInExistingSessionManager(params: {
   sessionManager: SessionManager;
   contextWindowTokens: number;
   maxCharsOverride?: number;
+  agentId?: string;
   sessionFile?: string;
   sessionId?: string;
   sessionKey?: string;
@@ -655,6 +656,8 @@ function truncateOversizedToolResultsInExistingSessionManager(params: {
   });
   if (rewriteResult.changed && params.sessionFile) {
     emitSessionTranscriptUpdate({
+      ...(params.agentId ? { agentId: params.agentId } : {}),
+      ...(params.sessionId ? { sessionId: params.sessionId } : {}),
       sessionFile: params.sessionFile,
       sessionKey: params.sessionKey,
     });
@@ -679,6 +682,7 @@ async function truncateOversizedToolResultsInTranscriptState(params: {
   sessionFile: string;
   contextWindowTokens: number;
   maxCharsOverride?: number;
+  agentId?: string;
   sessionId?: string;
   sessionKey?: string;
   config?: unknown;
@@ -722,6 +726,8 @@ async function truncateOversizedToolResultsInTranscriptState(params: {
       appendedEntries: rewriteResult.appendedEntries,
     });
     emitSessionTranscriptUpdate({
+      ...(params.agentId ? { agentId: params.agentId } : {}),
+      ...(params.sessionId ? { sessionId: params.sessionId } : {}),
       sessionFile: params.sessionFile,
       sessionKey: params.sessionKey,
     });
@@ -745,6 +751,7 @@ export function truncateOversizedToolResultsInSessionManager(params: {
   sessionManager: SessionManager;
   contextWindowTokens: number;
   maxCharsOverride?: number;
+  agentId?: string;
   sessionFile?: string;
   sessionId?: string;
   sessionKey?: string;
@@ -762,6 +769,7 @@ export async function truncateOversizedToolResultsInSession(params: {
   sessionFile: string;
   contextWindowTokens: number;
   maxCharsOverride?: number;
+  agentId?: string;
   sessionId?: string;
   sessionKey?: string;
   config?: unknown;
@@ -774,6 +782,7 @@ export async function truncateOversizedToolResultsInSession(params: {
       state,
       contextWindowTokens,
       maxCharsOverride: params.maxCharsOverride,
+      agentId: params.agentId,
       sessionFile,
       sessionId: params.sessionId,
       sessionKey: params.sessionKey,
diff --git a/src/agents/pi-embedded-runner/transcript-rewrite.ts b/src/agents/pi-embedded-runner/transcript-rewrite.ts
index 5f47379e193..8ebffc53ab6 100644
--- a/src/agents/pi-embedded-runner/transcript-rewrite.ts
+++ b/src/agents/pi-embedded-runner/transcript-rewrite.ts
@@ -351,6 +351,7 @@ export function rewriteTranscriptEntriesInState(params: {
  */
 export async function rewriteTranscriptEntriesInSqliteTranscript(params: {
   transcriptPath: string;
+  agentId?: string;
   sessionId?: string;
   sessionKey?: string;
   request: TranscriptRewriteRequest;
@@ -369,6 +370,8 @@ export async function rewriteTranscriptEntriesInSqliteTranscript(params: {
         appendedEntries: result.appendedEntries,
       });
       emitSessionTranscriptUpdate({
+        ...(params.agentId ? { agentId: params.agentId } : {}),
+        ...(params.sessionId ? { sessionId: params.sessionId } : {}),
         sessionFile: params.transcriptPath,
         sessionKey: params.sessionKey,
       });
diff --git a/src/gateway/server-methods/chat.ts b/src/gateway/server-methods/chat.ts
index 7cb52183cc0..7586bf1a65a 100644
--- a/src/gateway/server-methods/chat.ts
+++ b/src/gateway/server-methods/chat.ts
@@ -1016,6 +1016,8 @@ function extractTranscriptUserText(content: unknown): string | undefined {
 
 async function rewriteChatSendUserTurnMediaPaths(params: {
   transcriptPath: string;
+  agentId: string;
+  sessionId: string;
   sessionKey: string;
   message: string;
   savedImages: SavedMedia[];
@@ -1062,6 +1064,8 @@ async function rewriteChatSendUserTurnMediaPaths(params: {
   };
   await rewriteTranscriptEntriesInSqliteTranscript({
     transcriptPath: params.transcriptPath,
+    agentId: params.agentId,
+    sessionId: params.sessionId,
     sessionKey: params.sessionKey,
     config: params.cfg,
     request: {
@@ -2310,6 +2314,8 @@ export const chatHandlers: GatewayRequestHandlers = {
         transcriptMediaRewriteDone = true;
         await rewriteChatSendUserTurnMediaPaths({
           transcriptPath,
+          agentId,
+          sessionId: resolvedSessionId,
           sessionKey,
           message: parsedMessage,
           savedImages: await persistedImagesPromise,