diff --git a/src/node/services/agentSession.ts b/src/node/services/agentSession.ts
index 8314d34e3..9f2ebee92 100644
--- a/src/node/services/agentSession.ts
+++ b/src/node/services/agentSession.ts
@@ -3,6 +3,7 @@ import { EventEmitter } from "events";
 import * as path from "path";
 import { stat, readFile } from "fs/promises";
 import { PlatformPaths } from "@/common/utils/paths";
+import { log } from "@/node/services/log";
 import { createMuxMessage } from "@/common/types/message";
 import type { Config } from "@/node/config";
 import type { AIService } from "@/node/services/aiService";
@@ -247,48 +248,57 @@ export class AgentSession {
   private async emitHistoricalEvents(
     listener: (event: AgentSessionChatEvent) => void
   ): Promise<void> {
-    // Read partial BEFORE iterating history so we can skip the corresponding
-    // placeholder message (which has empty parts). The partial has the real content.
-    const streamInfo = this.aiService.getStreamInfo(this.workspaceId);
-    const partial = await this.partialService.readPartial(this.workspaceId);
-    const partialHistorySequence = partial?.metadata?.historySequence;
-
-    // Load chat history (persisted messages from chat.jsonl)
-    const historyResult = await this.historyService.getHistory(this.workspaceId);
-    if (historyResult.success) {
-      for (const message of historyResult.data) {
-        // Skip the placeholder message if we have a partial with the same historySequence.
-        // The placeholder has empty parts; the partial has the actual content.
-        // Without this, both get loaded and the empty placeholder may be shown as "last message".
-        if (
-          partialHistorySequence !== undefined &&
-          message.metadata?.historySequence === partialHistorySequence
-        ) {
-          continue;
+    // try/catch/finally guarantees caught-up is always sent, even if replay fails.
+    // Without caught-up, the frontend stays in "Loading workspace..." forever.
+    try {
+      // Read partial BEFORE iterating history so we can skip the corresponding
+      // placeholder message (which has empty parts). The partial has the real content.
+      const streamInfo = this.aiService.getStreamInfo(this.workspaceId);
+      const partial = await this.partialService.readPartial(this.workspaceId);
+      const partialHistorySequence = partial?.metadata?.historySequence;
+
+      // Load chat history (persisted messages from chat.jsonl)
+      const historyResult = await this.historyService.getHistory(this.workspaceId);
+      if (historyResult.success) {
+        for (const message of historyResult.data) {
+          // Skip the placeholder message if we have a partial with the same historySequence.
+          // The placeholder has empty parts; the partial has the actual content.
+          // Without this, both get loaded and the empty placeholder may be shown as "last message".
+          if (
+            partialHistorySequence !== undefined &&
+            message.metadata?.historySequence === partialHistorySequence
+          ) {
+            continue;
+          }
+          // Add type: "message" for discriminated union (messages from chat.jsonl don't have it)
+          listener({ workspaceId: this.workspaceId, message: { ...message, type: "message" } });
         }
-        // Add type: "message" for discriminated union (messages from chat.jsonl don't have it)
-        listener({ workspaceId: this.workspaceId, message: { ...message, type: "message" } });
       }
-    }
-
-    if (streamInfo) {
-      await this.aiService.replayStream(this.workspaceId);
-    } else if (partial) {
-      // Add type: "message" for discriminated union (partials from disk don't have it)
-      listener({ workspaceId: this.workspaceId, message: { ...partial, type: "message" } });
-    }
 
-    // Replay init state BEFORE caught-up (treat as historical data)
-    // This ensures init events are buffered correctly by the frontend,
-    // preserving their natural timing characteristics from the hook execution.
-    await this.initStateManager.replayInit(this.workspaceId);
+      if (streamInfo) {
+        await this.aiService.replayStream(this.workspaceId);
+      } else if (partial) {
+        // Add type: "message" for discriminated union (partials from disk don't have it)
+        listener({ workspaceId: this.workspaceId, message: { ...partial, type: "message" } });
+      }
 
-    // Send caught-up after ALL historical data (including init events)
-    // This signals frontend that replay is complete and future events are real-time
-    listener({
-      workspaceId: this.workspaceId,
-      message: { type: "caught-up" },
-    });
+      // Replay init state BEFORE caught-up (treat as historical data)
+      // This ensures init events are buffered correctly by the frontend,
+      // preserving their natural timing characteristics from the hook execution.
+      await this.initStateManager.replayInit(this.workspaceId);
+    } catch (error) {
+      log.error("Failed to replay history for workspace", {
+        workspaceId: this.workspaceId,
+        error,
+      });
+    } finally {
+      // Send caught-up after ALL historical data (including init events)
+      // This signals frontend that replay is complete and future events are real-time
+      listener({
+        workspaceId: this.workspaceId,
+        message: { type: "caught-up" },
+      });
+    }
   }
 
   async ensureMetadata(args: {