diff --git a/agent/context_compressor.py b/agent/context_compressor.py
index b0d92fc011d..6ee5d6cffea 100644
--- a/agent/context_compressor.py
+++ b/agent/context_compressor.py
@@ -95,6 +95,15 @@ _SUMMARY_END_MARKER = (
     "respond to the message below, not the summary above ---"
 )
 
+# When the summary must be merged into the first tail message (the alternation
+# corner case where a standalone summary role would collide with both head and
+# tail), the tail message's own prior content is preserved BEFORE the summary,
+# wrapped in these delimiters so the model doesn't read it as a fresh message.
+# The summary prefix therefore lands AFTER _MERGED_SUMMARY_DELIMITER rather than
+# at the start of the message, so _is_context_summary_content must look past it.
+_MERGED_PRIOR_CONTEXT_HEADER = "[PRIOR CONTEXT — for reference only; not a new message]"
+_MERGED_SUMMARY_DELIMITER = "[END OF PRIOR CONTEXT — COMPACTION SUMMARY BELOW]"
+
 # Handoff prefixes that shipped in earlier releases. A summary persisted under
 # one of these can be inherited into a resumed lineage (#35344); when it is
 # re-normalized on re-compaction we must strip the OLD prefix too, otherwise the
@@ -2007,6 +2016,13 @@ This compaction should PRIORITISE preserving all information related to the focu
         stale directive it carried stays embedded in the body.
         """
         text = (summary or "").strip()
+        # Merge-into-tail summaries wrap prior tail content before the summary
+        # body. Drop everything up to and including the delimiter so only the
+        # real summary body is carried forward on re-compaction — otherwise the
+        # [PRIOR CONTEXT] header and stale tail content leak into the next
+        # summarizer prompt.
+        if _MERGED_SUMMARY_DELIMITER in text:
+            text = text.split(_MERGED_SUMMARY_DELIMITER, 1)[1].strip()
         for prefix in (SUMMARY_PREFIX, LEGACY_SUMMARY_PREFIX, *_HISTORICAL_SUMMARY_PREFIXES):
             if text.startswith(prefix):
                 text = text[len(prefix):].lstrip()
@@ -2027,6 +2043,13 @@ This compaction should PRIORITISE preserving all information related to the focu
     @staticmethod
     def _is_context_summary_content(content: Any) -> bool:
         text = _content_text_for_contains(content).lstrip()
+        # Merge-into-tail summaries wrap prior tail content before the summary,
+        # so the handoff prefix lands after _MERGED_SUMMARY_DELIMITER rather than
+        # at the start. Detect the summary in that region too, otherwise callers
+        # (auto-focus skip, carry-forward summary find, last-real-user anchor)
+        # mistake a merged summary message for a real user turn.
+        if _MERGED_SUMMARY_DELIMITER in text:
+            text = text.split(_MERGED_SUMMARY_DELIMITER, 1)[1].lstrip()
         if text.startswith(SUMMARY_PREFIX) or text.startswith(LEGACY_SUMMARY_PREFIX):
             return True
         return any(text.startswith(p) for p in _HISTORICAL_SUMMARY_PREFIXES)
@@ -2898,13 +2921,13 @@ This compaction should PRIORITISE preserving all information related to the focu
                 # before the summary.
                 old_content = msg.get("content", "")
                 suffix = (
-                    "\n\n[END OF PRIOR CONTEXT — COMPACTION SUMMARY BELOW]\n\n"
+                    "\n\n" + _MERGED_SUMMARY_DELIMITER + "\n\n"
                     + summary + "\n\n"
                     + _SUMMARY_END_MARKER
                 )
                 msg["content"] = _append_text_to_content(
                     _append_text_to_content(old_content, suffix, prepend=False),
-                    "[PRIOR CONTEXT — for reference only; not a new message]\n",
+                    _MERGED_PRIOR_CONTEXT_HEADER + "\n",
                     prepend=True,
                 )
                 # Mark the merged message so frontends can identify it as
diff --git a/tests/agent/test_compressor_assistant_tail_anchor.py b/tests/agent/test_compressor_assistant_tail_anchor.py
index 68d2d9f14eb..a8be6dc3fef 100644
--- a/tests/agent/test_compressor_assistant_tail_anchor.py
+++ b/tests/agent/test_compressor_assistant_tail_anchor.py
@@ -357,7 +357,10 @@ class TestCompactionRollupReproduction:
     in ``web/src/pages/SessionsPage.tsx``)."""
 
     def test_compress_keeps_visible_reply_text(self, compressor):
-        from agent.context_compressor import SUMMARY_PREFIX
+        from agent.context_compressor import (
+            SUMMARY_PREFIX,
+            COMPRESSED_SUMMARY_METADATA_KEY,
+        )
         c = compressor
         c.tail_token_budget = 10
         # ``_generate_summary`` normally wraps the LLM body in
@@ -392,10 +395,12 @@ class TestCompactionRollupReproduction:
             return_value=_mocked,
         ):
             result = c.compress(messages, current_tokens=90_000)
-        # 1. A summary message exists (compression actually ran).
+        # 1. A summary message exists (compression actually ran). Detect via
+        # the canonical metadata key rather than a content prefix: merge-into-
+        # tail summaries wrap prior content before the summary, so the prefix
+        # is no longer at the start of the message content (#56372).
         assert any(
-            isinstance(m.get("content"), str)
-            and m["content"].startswith(SUMMARY_PREFIX)
+            m.get(COMPRESSED_SUMMARY_METADATA_KEY)
             for m in result
         ), "compress() did not insert a summary message"
         # 2. The visible reply text must survive somewhere — either
@@ -419,7 +424,10 @@ class TestCompactionRollupReproduction:
         as its OWN assistant message — not merged with anything.
         This is the common case; the merge-into-tail path is the
         edge case for double-collision."""
-        from agent.context_compressor import SUMMARY_PREFIX
+        from agent.context_compressor import (
+            SUMMARY_PREFIX,
+            COMPRESSED_SUMMARY_METADATA_KEY,
+        )
         c = compressor
         c.tail_token_budget = 10
         _mocked = f"{SUMMARY_PREFIX}\nrolled-up middle summary"
@@ -449,11 +457,11 @@ class TestCompactionRollupReproduction:
             return_value=_mocked,
         ):
             result = c.compress(messages, current_tokens=90_000)
-        # Standalone summary present:
+        # Summary present (detect via the canonical metadata key — merge-into-
+        # tail summaries no longer start with SUMMARY_PREFIX after #56372):
         summary_rows = [
             m for m in result
-            if isinstance(m.get("content"), str)
-            and m["content"].startswith(SUMMARY_PREFIX)
+            if m.get(COMPRESSED_SUMMARY_METADATA_KEY)
         ]
         assert len(summary_rows) == 1
         # Visible reply as its OWN distinct assistant message
@@ -463,7 +471,7 @@ class TestCompactionRollupReproduction:
             if m.get("role") == "assistant"
             and isinstance(m.get("content"), str)
             and "THE VISIBLE REPLY THE USER JUST READ" in m["content"]
-            and not m["content"].startswith(SUMMARY_PREFIX)
+            and not m.get(COMPRESSED_SUMMARY_METADATA_KEY)
         ]
         assert len(reply_rows) == 1, (
             "REGRESSION (#29824): expected exactly one standalone "
diff --git a/tests/agent/test_context_compressor.py b/tests/agent/test_context_compressor.py
index ee95e8a6e4d..026ee37d951 100644
--- a/tests/agent/test_context_compressor.py
+++ b/tests/agent/test_context_compressor.py
@@ -2009,6 +2009,42 @@ class TestCompressWithClient:
         assert text.index("SUMMARY_BODY") < text.index(end)
         assert text.rstrip().endswith(end)
 
+    def test_merged_tail_summary_still_detected_and_stripped(self):
+        """Regression for #56372 salvage: the merge-into-tail reorder moves the
+        summary prefix AFTER the [PRIOR CONTEXT] wrapper, so content-prefix
+        detection (_is_context_summary_content) and body extraction
+        (_strip_summary_prefix) must look past the delimiter. Otherwise a merged
+        summary is mistaken for a real user turn (breaking the last-real-user
+        anchor and carry-forward summary find) and the wrapper + stale tail
+        content leaks into the next summarizer prompt.
+        """
+        from agent.context_compressor import (
+            SUMMARY_PREFIX,
+            _SUMMARY_END_MARKER,
+            _MERGED_PRIOR_CONTEXT_HEADER,
+            _MERGED_SUMMARY_DELIMITER,
+        )
+
+        merged = (
+            _MERGED_PRIOR_CONTEXT_HEADER + "\n"
+            "old tail content here\n\n"
+            + _MERGED_SUMMARY_DELIMITER + "\n\n"
+            + SUMMARY_PREFIX + "\nTHE_SUMMARY_BODY\n\n"
+            + _SUMMARY_END_MARKER
+        )
+
+        # Detected as a summary despite the prefix not being at the start.
+        assert ContextCompressor._is_context_summary_content(merged) is True
+        # Stripping yields only the real summary body — no wrapper, no stale
+        # tail content, no prefix, no end marker.
+        body = ContextCompressor._strip_summary_prefix(merged)
+        assert body == "THE_SUMMARY_BODY"
+
+        # Standalone (non-merged) summaries still work unchanged.
+        standalone = SUMMARY_PREFIX + "\nSTANDALONE_BODY\n\n" + _SUMMARY_END_MARKER
+        assert ContextCompressor._is_context_summary_content(standalone) is True
+        assert ContextCompressor._strip_summary_prefix(standalone) == "STANDALONE_BODY"
+
     def test_double_collision_user_head_assistant_tail(self):
         """Reverse double collision: head ends with 'user', tail starts with 'assistant'.
         summary='assistant' collides with tail, 'user' collides with head → merge."""