diff --git a/src/agents/command/attempt-execution.helpers.ts b/src/agents/command/attempt-execution.helpers.ts
index 784603f60cc..7c55f727f5b 100644
--- a/src/agents/command/attempt-execution.helpers.ts
+++ b/src/agents/command/attempt-execution.helpers.ts
@@ -185,13 +185,13 @@ async function jsonlFileHasOrphanedTrailingToolUse(filePath: string): Promise<bo
         }
         const message = rec?.message as Record<string, unknown> | undefined;
         const role = message?.role;
-        const blocks = toToolContentBlocks(message?.content);
-        if (!blocks) {
-          continue;
-        }
         if (role === "assistant") {
           lastAssistantToolUseIds = new Set();
           answeredToolResultIds = new Set();
+          const blocks = toToolContentBlocks(message?.content);
+          if (!blocks) {
+            continue;
+          }
           for (const block of blocks) {
             if (isClaudeTranscriptToolUseBlock(block)) {
               const id = resolveToolUseId(block);
@@ -206,6 +206,10 @@ async function jsonlFileHasOrphanedTrailingToolUse(filePath: string): Promise<bo
             }
           }
         } else if (role === "user") {
+          const blocks = toToolContentBlocks(message?.content);
+          if (!blocks) {
+            continue;
+          }
           for (const block of blocks) {
             if (isClaudeTranscriptToolResultBlock(block)) {
               const id = resolveToolUseId(block);
diff --git a/src/agents/command/attempt-execution.test.ts b/src/agents/command/attempt-execution.test.ts
index 038f6fcb27c..9c15ae9e388 100644
--- a/src/agents/command/attempt-execution.test.ts
+++ b/src/agents/command/attempt-execution.test.ts
@@ -934,6 +934,29 @@ describe("claudeCliSessionTranscriptHasOrphanedToolUse", () => {
     ).toBe(false);
   });
 
+  it("returns false when a later string assistant message supersedes an old orphan", async () => {
+    await writeJsonlSession("buried-string", [
+      {
+        type: "assistant",
+        message: {
+          role: "assistant",
+          content: [{ type: "tool_use", id: "toolu_old_string", name: "Bash", input: {} }],
+        },
+      },
+      {
+        type: "assistant",
+        message: { role: "assistant", content: "moving on" },
+      },
+    ]);
+    expect(
+      await claudeCliSessionTranscriptHasOrphanedToolUse({
+        sessionId: "buried-string",
+        workspaceDir,
+        homeDir: tmpDir,
+      }),
+    ).toBe(false);
+  });
+
   it("rejects path-like session ids instead of escaping the Claude projects tree", async () => {
     await writeJsonlSession("safe", []);
     expect(