diff --git a/agent/context_compressor.py b/agent/context_compressor.py
index 6859a28a0..48b97bda7 100644
--- a/agent/context_compressor.py
+++ b/agent/context_compressor.py
@@ -2224,9 +2224,21 @@ This compaction should PRIORITISE preserving all information related to the focu
     def _find_last_user_message_idx(
         self, messages: List[Dict[str, Any]], head_end: int
     ) -> int:
-        """Return the index of the last user-role message at or after *head_end*, or -1."""
+        """Return the index of the last user-role message at or after *head_end*, or -1.
+
+        A context-compaction handoff banner can be inserted as a ``role="user"``
+        message (see the summary-role selection in ``compress``). It is internal
+        continuity state, not a real user turn, so it must not be picked as the
+        tail anchor — otherwise ``_ensure_last_user_message_in_tail`` protects
+        the summary and rolls the genuine last user message into the next
+        compaction, re-triggering the active-task loss the anchor exists to
+        prevent.
+        """
         for i in range(len(messages) - 1, head_end - 1, -1):
-            if messages[i].get("role") == "user":
+            msg = messages[i]
+            if msg.get("role") == "user" and not self._is_context_summary_content(
+                msg.get("content")
+            ):
                 return i
         return -1
 
diff --git a/tests/agent/test_compressor_assistant_tail_anchor.py b/tests/agent/test_compressor_assistant_tail_anchor.py
index e28bc8213..68d2d9f14 100644
--- a/tests/agent/test_compressor_assistant_tail_anchor.py
+++ b/tests/agent/test_compressor_assistant_tail_anchor.py
@@ -477,6 +477,51 @@ class TestCompactionRollupReproduction:
 # ---------------------------------------------------------------------------
 
 
+class TestFindLastUserMessageIdxSkipsSummaryMarker:
+    """A context-compaction handoff banner is inserted with ``role="user"``
+    when the head ends in an assistant/tool message (see the summary-role
+    selection in ``compress``). ``_find_last_user_message_idx`` must NOT treat
+    that banner as the latest user turn — otherwise, on a resumed or
+    multi-compaction session, ``_ensure_last_user_message_in_tail`` anchors the
+    tail to the summary and rolls the genuine last user message into the next
+    compaction, re-triggering the active-task loss the anchor exists to prevent.
+    (Salvaged from #36626 / issue #36624.)
+    """
+
+    def test_skips_user_role_context_summary_marker(self, compressor):
+        from agent.context_compressor import SUMMARY_PREFIX
+
+        messages = [
+            {"role": "system", "content": "sys"},
+            {"role": "user", "content": "REAL current task"},
+            {"role": "assistant", "content": "working on it"},
+            # A handoff summary re-inserted as a user-role message after resume.
+            {"role": "user", "content": f"{SUMMARY_PREFIX}\n## Active Task\nold"},
+            {"role": "assistant", "content": "continuing from the real task"},
+        ]
+        # Latest *real* user message is index 1, not the summary at index 3.
+        assert compressor._find_last_user_message_idx(messages, head_end=1) == 1
+
+    def test_returns_real_user_when_no_summary_present(self, compressor):
+        messages = [
+            {"role": "system", "content": "sys"},
+            {"role": "user", "content": "first"},
+            {"role": "assistant", "content": "reply"},
+            {"role": "user", "content": "second"},
+        ]
+        assert compressor._find_last_user_message_idx(messages, head_end=1) == 3
+
+    def test_all_user_messages_are_summaries_returns_minus_one(self, compressor):
+        from agent.context_compressor import SUMMARY_PREFIX
+
+        messages = [
+            {"role": "system", "content": "sys"},
+            {"role": "assistant", "content": "reply"},
+            {"role": "user", "content": f"{SUMMARY_PREFIX}\nhandoff"},
+        ]
+        assert compressor._find_last_user_message_idx(messages, head_end=1) == -1
+
+
 class TestSourceGuardrail:
     @pytest.fixture
     def source(self) -> str: