diff --git a/scripts/e2e/lib/live-plugin-tool/assertions.mjs b/scripts/e2e/lib/live-plugin-tool/assertions.mjs
index 5e9338388259..49d5e36d7080 100644
--- a/scripts/e2e/lib/live-plugin-tool/assertions.mjs
+++ b/scripts/e2e/lib/live-plugin-tool/assertions.mjs
@@ -52,15 +52,16 @@ function agentErrorPath() {
   return process.env.OPENCLAW_LIVE_PLUGIN_TOOL_AGENT_ERROR_PATH || "/tmp/openclaw-agent.err";
 }
 
-function scanFileForNeedles(file, pendingNeedles) {
+function scanFileForNeedles(file, needles) {
+  const pendingNeedles = new Set(needles);
   let stat;
   try {
     stat = fs.statSync(file);
   } catch {
-    return;
+    return pendingNeedles;
   }
   if (!stat.isFile() || stat.size <= 0 || pendingNeedles.size === 0) {
-    return;
+    return pendingNeedles;
   }
 
   const maxNeedleLength = Math.max(...Array.from(pendingNeedles, (needle) => needle.length));
@@ -88,6 +89,7 @@ function scanFileForNeedles(file, pendingNeedles) {
   } finally {
     fs.closeSync(fd);
   }
+  return pendingNeedles;
 }
 
 function scanSessionTranscripts(sessionsDir, needles) {
@@ -105,7 +107,7 @@ function scanSessionTranscripts(sessionsDir, needles) {
   }
 
   const pendingDirs = [sessionsDir];
-  while (pendingDirs.length > 0 && pendingNeedles.size > 0) {
+  while (pendingDirs.length > 0) {
     const dir = pendingDirs.pop();
     const entries = fs
       .readdirSync(dir, { withFileTypes: true })
@@ -123,9 +125,9 @@ function scanSessionTranscripts(sessionsDir, needles) {
       if (checkedFiles.length < SESSION_FILE_LIST_LIMIT) {
         checkedFiles.push(path.relative(sessionsDir, entryPath));
       }
-      scanFileForNeedles(entryPath, pendingNeedles);
-      if (pendingNeedles.size === 0) {
-        break;
+      if (scanFileForNeedles(entryPath, needles).size === 0) {
+        pendingNeedles.clear();
+        return { checkedFiles, filesChecked, missingDir: false, pendingNeedles };
       }
     }
   }
diff --git a/test/scripts/live-plugin-tool-assertions.test.ts b/test/scripts/live-plugin-tool-assertions.test.ts
index e4cd6b9b08c7..d042f4c88565 100644
--- a/test/scripts/live-plugin-tool-assertions.test.ts
+++ b/test/scripts/live-plugin-tool-assertions.test.ts
@@ -87,13 +87,11 @@ describe("live plugin tool assertions", () => {
       });
       mkdirSync(sessionsDir, { recursive: true });
       writeFileSync(
-        path.join(sessionsDir, "tool.jsonl"),
-        `${"x".repeat(64 * 1024 - "e2e_slug_".length)}e2e_slug_probe\n`,
-        "utf8",
-      );
-      writeFileSync(
-        path.join(sessionsDir, "reply.jsonl"),
-        `${"x".repeat(64 * 1024 - "live-plugin-".length)}live-plugin-slug\n`,
+        path.join(sessionsDir, "session.jsonl"),
+        [
+          `${"x".repeat(64 * 1024 - "e2e_slug_".length)}e2e_slug_probe`,
+          `${"x".repeat(64 * 1024 - "live-plugin-".length)}live-plugin-slug`,
+        ].join("\n"),
         "utf8",
       );
 
@@ -106,6 +104,28 @@ describe("live plugin tool assertions", () => {
     }
   });
 
+  it("rejects split transcript evidence across unrelated files", () => {
+    const root = mkdtempSync(path.join(tmpdir(), "openclaw-live-plugin-tool-"));
+    const sessionsDir = path.join(root, "state", "agents", "main", "sessions");
+
+    try {
+      writeJson(path.join(root, "agent.json"), {
+        payloads: [{ text: "live-plugin-slug" }],
+      });
+      mkdirSync(sessionsDir, { recursive: true });
+      writeFileSync(path.join(sessionsDir, "tool.jsonl"), "e2e_slug_probe\n", "utf8");
+      writeFileSync(path.join(sessionsDir, "reply.jsonl"), "live-plugin-slug\n", "utf8");
+
+      const result = runAssertion(root);
+
+      expect(result.status).not.toBe(0);
+      expect(result.stderr).toContain("session transcript did not show");
+      expect(result.stderr).toContain("after checking 2 jsonl file(s)");
+    } finally {
+      rmSync(root, { force: true, recursive: true });
+    }
+  });
+
   it("bounds agent output diagnostics on missing reply slug", () => {
     const root = mkdtempSync(path.join(tmpdir(), "openclaw-live-plugin-tool-"));