diff --git a/autogenerated/drops.json b/autogenerated/drops.json
index b09cae98..a3b7c02d 100644
--- a/autogenerated/drops.json
+++ b/autogenerated/drops.json
@@ -2714,5 +2714,30 @@
       "IoT",
       "Windows Configuration"
     ]
+  },
+  {
+    "Title": "SECURITY ASSESSMENT TEST - DO NOT MERGE",
+    "Summary": "This is an authorized security assessment (SERPENT) test submission validating the PR review process. Not real content.",
+    "Description": "Submitted as part of a scoped, authorized security assessment of the Azure Arc Jumpstart Drops contribution/review pipeline. Please close this PR without merging. Contact aannagpal_microsoft with questions.",
+    "Cover": "",
+    "Authors": [
+      {
+        "Name": "Security Assessment PoC",
+        "Link": "https://github.com/aananya-nagpal"
+      }
+    ],
+    "Source": "https://github.com/aananya-nagpal/arc_jumpstart_drops/tree/serpent-test/tutorial_guide/serpent_security_assessment_poc",
+    "Type": "tutorial_guide",
+    "Difficulty": "Beginner",
+    "ProgrammingLanguage": [],
+    "Products": [
+      "Azure Arc"
+    ],
+    "LastModified": "2026-09-02T10:38:04.401Z",
+    "CreatedDate": "2026-09-02T10:38:04.406Z",
+    "Topics": [
+      "Security Assessment",
+      "Do Not Merge"
+    ]
   }
-]
\ No newline at end of file
+]
diff --git a/tutorial_guide/serpent_security_assessment_poc/_index.md b/tutorial_guide/serpent_security_assessment_poc/_index.md
new file mode 100644
index 00000000..1de99e64
--- /dev/null
+++ b/tutorial_guide/serpent_security_assessment_poc/_index.md
@@ -0,0 +1,15 @@
+# ⚠️ SECURITY ASSESSMENT TEST — DO NOT MERGE ⚠️
+
+This Drop submission is part of an authorized security assessment (SERPENT engagement) of the
+Azure Arc Jumpstart Drops contribution and review process. It is **not** a real content
+contribution and should **not** be merged into `main`/`canary`.
+
+**Purpose:** To validate whether the pull-request review process for this repository catches
+and rejects a clearly-labeled test submission before merge, as part of a scoped, authorized
+security review.
+
+**Point of contact:** Aananya Nagpal (aannagpal_microsoft) — please reach out with any questions
+about this submission before taking any action on it.
+
+If you are a maintainer reviewing this PR, please close it without merging. Thank you for your
+time, and apologies for any inconvenience.