diff --git a/packages/server/src/server/agent/providers/claude/agent.history-load.test.ts b/packages/server/src/server/agent/providers/claude/agent.history-load.test.ts
new file mode 100644
index 0000000000..223e2001f5
--- /dev/null
+++ b/packages/server/src/server/agent/providers/claude/agent.history-load.test.ts
@@ -0,0 +1,93 @@
+import { mkdirSync, mkdtempSync, rmSync } from "node:fs";
+import * as os from "node:os";
+import * as path from "node:path";
+import pino from "pino";
+import { afterEach, beforeEach, describe, expect, test, vi } from "vitest";
+
+import { ClaudeAgentClient } from "./agent.js";
+import { claudeProjectDirSync } from "./project-dir.js";
+
+/**
+ * A resumed Claude agent whose transcript is missing or unreadable opens with an empty timeline.
+ * The daemon log at its default level has to say which, and where it looked.
+ */
+
+const SESSION_ID = "history-load-session";
+
+interface LogRecord {
+  level: number;
+  msg: string;
+  sessionId?: string;
+  historyPath?: string;
+  err?: { message?: string };
+}
+
+describe("ClaudeAgentSession persisted history load", () => {
+  let tempRoot: string;
+  let cwd: string;
+  let configDir: string;
+  let records: LogRecord[];
+
+  async function resume(): Promise<void> {
+    const client = new ClaudeAgentClient({
+      logger: pino({ level: "info" }, { write: (line: string) => records.push(JSON.parse(line)) }),
+      queryFactory: vi.fn(() => {
+        throw new Error("history load must not start a query");
+      }),
+      resolveVersion: async () => "2.1.220",
+    });
+    const session = await client.resumeSession(
+      { provider: "claude", sessionId: SESSION_ID },
+      { cwd },
+    );
+    await session.close();
+  }
+
+  function transcriptPath(): string {
+    return path.join(claudeProjectDirSync(cwd, { configDir }), `${SESSION_ID}.jsonl`);
+  }
+
+  beforeEach(() => {
+    tempRoot = mkdtempSync(path.join(os.tmpdir(), "claude-history-load-"));
+    cwd = path.join(tempRoot, "repo");
+    configDir = path.join(tempRoot, "claude-config");
+    mkdirSync(cwd, { recursive: true });
+    vi.stubEnv("CLAUDE_CONFIG_DIR", configDir);
+    records = [];
+  });
+
+  afterEach(() => {
+    vi.unstubAllEnvs();
+    rmSync(tempRoot, { recursive: true, force: true });
+  });
+
+  test("logs the resolved transcript path when the transcript does not exist", async () => {
+    await resume();
+
+    expect(records).toContainEqual(
+      expect.objectContaining({
+        level: pino.levels.values.info,
+        msg: "No Claude transcript to load history from",
+        sessionId: SESSION_ID,
+        historyPath: transcriptPath(),
+      }),
+    );
+  });
+
+  test("logs a warning with the error when the transcript cannot be read", async () => {
+    // A directory at the transcript path exists but cannot be read as a file.
+    mkdirSync(transcriptPath(), { recursive: true });
+
+    await resume();
+
+    expect(records).toContainEqual(
+      expect.objectContaining({
+        level: pino.levels.values.warn,
+        msg: "Failed to load Claude history from transcript",
+        sessionId: SESSION_ID,
+        historyPath: transcriptPath(),
+        err: expect.objectContaining({ message: expect.stringContaining("EISDIR") }),
+      }),
+    );
+  });
+});
diff --git a/packages/server/src/server/agent/providers/claude/agent.ts b/packages/server/src/server/agent/providers/claude/agent.ts
index b6a366370b..e5153e2102 100644
--- a/packages/server/src/server/agent/providers/claude/agent.ts
+++ b/packages/server/src/server/agent/providers/claude/agent.ts
@@ -4881,10 +4881,15 @@ class ClaudeAgentSession implements AgentSession {
   }
 
   private loadPersistedHistory(sessionId: string): void {
+    let historyPath: string | null = null;
     try {
       this.taskState.reset();
-      const historyPath = this.resolveHistoryPath(sessionId);
+      historyPath = this.resolveHistoryPath(sessionId);
       if (!historyPath || !fs.existsSync(historyPath)) {
+        this.logger.info(
+          { sessionId, cwd: this.config.cwd, historyPath },
+          "No Claude transcript to load history from",
+        );
         return;
       }
       const content = fs.readFileSync(historyPath, "utf8");
@@ -4893,8 +4898,11 @@ class ClaudeAgentSession implements AgentSession {
         readClaudeSidechainHistory(historyPath),
       );
       this.ingestPersistedHistory(content, replay);
-    } catch {
-      // ignore history load failures
+    } catch (error) {
+      this.logger.warn(
+        { err: error, sessionId, historyPath },
+        "Failed to load Claude history from transcript",
+      );
     }
   }