fix(session): prevent duplicate archive and message loss in enforce_file_cap

When retain_recent_legal_suffix hits the else branch (tail has no user
messages), it takes a non-contiguous slice from the middle of the session.
enforce_file_cap incorrectly assumed dropped messages were always a prefix
(before[:dropped_count]), causing user messages to be both archived and
retained, and some messages to silently disappear.

Fix by having retain_recent_legal_suffix return the actual dropped message
list using identity-based diff, so enforce_file_cap no longer needs to
guess which messages were removed.

nanobot/session/manager.py

@@ -269,13 +269,19 @@ class Session:
         self.updated_at = datetime.now()
         self.metadata.pop("_last_summary", None)
 
-    def retain_recent_legal_suffix(self, max_messages: int) -> None:
+    def retain_recent_legal_suffix(self, max_messages: int) -> list[dict]:
-        """Keep a legal recent suffix constrained by a hard message cap."""
+        """Keep a legal recent suffix constrained by a hard message cap.
+
+        Returns the list of messages that were removed.
+        """
         if max_messages <= 0:
+            dropped = list(self.messages)
             self.clear()
-            return
+            return dropped
         if len(self.messages) <= max_messages:
-            return
+            return []
+
+        original = list(self.messages)
 
         retained = list(self.messages[-max_messages:])
 
@@ -306,10 +312,16 @@ class Session:
             if start:
                 retained = retained[start:]
 
-        dropped = len(self.messages) - len(retained)
+        # Compute actually-dropped messages using identity comparison so that
+        # even when retained is a non-contiguous slice of original (the else
+        # branch above), we never duplicate or lose messages.
+        retained_ids = set(id(m) for m in retained)
+        dropped = [m for m in original if id(m) not in retained_ids]
+
         self.messages = retained
-        self.last_consolidated = max(0, self.last_consolidated - dropped)
+        self.last_consolidated = max(0, self.last_consolidated - len(dropped))
         self.updated_at = datetime.now()
+        return dropped
 
     def enforce_file_cap(
         self,
@@ -320,23 +332,19 @@ class Session:
         if limit <= 0 or len(self.messages) <= limit:
             return
 
-        before = list(self.messages)
         before_last_consolidated = self.last_consolidated
-        before_count = len(before)
+        dropped = self.retain_recent_legal_suffix(limit)
-        self.retain_recent_legal_suffix(limit)
+        if not dropped:
-        dropped_count = before_count - len(self.messages)
-        if dropped_count <= 0:
             return
 
-        dropped = before[:dropped_count]
+        already_consolidated = min(before_last_consolidated, len(dropped))
-        already_consolidated = min(before_last_consolidated, dropped_count)
         archive_chunk = dropped[already_consolidated:]
         if archive_chunk and on_archive:
             on_archive(archive_chunk)
         logger.info(
             "Session file cap hit for {}: dropped {}, raw-archived {}, kept {}",
             self.key,
-            dropped_count,
+            len(dropped),
             len(archive_chunk),
             len(self.messages),
         )

tests/agent/test_session_manager_history.py

@@ -538,3 +538,105 @@ def test_retain_recent_legal_suffix_hard_cap_with_long_non_user_chain():
     session.retain_recent_legal_suffix(6)
 
     assert len(session.messages) <= 6
+
+
+# --- enforce_file_cap archive correctness (issue #4128) ---
+
+
+def test_retain_recent_legal_suffix_returns_dropped_messages():
+    """retain_recent_legal_suffix returns the actually-dropped messages."""
+    session = Session(key="test:return-dropped")
+    for i in range(10):
+        session.messages.append({"role": "user", "content": f"msg{i}"})
+
+    dropped = session.retain_recent_legal_suffix(4)
+
+    assert len(dropped) == 6
+    assert [m["content"] for m in dropped] == [f"msg{i}" for i in range(6)]
+    assert len(session.messages) == 4
+
+
+def test_retain_recent_legal_suffix_returns_empty_when_no_drop():
+    """No messages dropped → empty list returned."""
+    session = Session(key="test:no-drop")
+    for i in range(3):
+        session.messages.append({"role": "user", "content": f"msg{i}"})
+
+    dropped = session.retain_recent_legal_suffix(4)
+
+    assert dropped == []
+    assert len(session.messages) == 3
+
+
+def test_retain_recent_legal_suffix_returns_all_on_zero():
+    """max_messages=0 clears session and returns all messages."""
+    session = Session(key="test:zero-return")
+    for i in range(5):
+        session.messages.append({"role": "user", "content": f"msg{i}"})
+
+    dropped = session.retain_recent_legal_suffix(0)
+
+    assert len(dropped) == 5
+    assert session.messages == []
+
+
+def test_enforce_file_cap_no_duplicate_archive_in_else_branch():
+    """When the tail is assistant-only, enforce_file_cap must not archive
+    messages that are also retained (the bug from issue #4128)."""
+    from unittest.mock import MagicMock
+
+    session = Session(key="test:else-archive")
+    # Build: 15 user messages, then 10 assistant messages (no user in tail)
+    for i in range(15):
+        session.messages.append({"role": "user", "content": f"u{i}"})
+    for i in range(10):
+        session.messages.append({"role": "assistant", "content": f"a{i}"})
+
+    archive_fn = MagicMock()
+    session.enforce_file_cap(on_archive=archive_fn, limit=6)
+
+    # Verify retained messages
+    retained_contents = [m["content"] for m in session.messages]
+    assert len(session.messages) <= 6
+
+    # Verify archived messages have NO overlap with retained
+    if archive_fn.called:
+        archived = archive_fn.call_args.args[0]
+        archived_ids = set(id(m) for m in archived)
+        retained_ids = set(id(m) for m in session.messages)
+        assert not archived_ids & retained_ids, (
+            f"Duplicate messages in archive and retained: "
+            f"overlap contents = {[m['content'] for m in archived if id(m) in retained_ids]}"
+        )
+
+
+def test_enforce_file_cap_no_message_loss_in_else_branch():
+    """In the else branch, no messages should silently disappear — every
+    message must be either retained or archived."""
+    from unittest.mock import MagicMock
+
+    session = Session(key="test:else-no-loss")
+    all_messages = []
+    for i in range(15):
+        msg = {"role": "user", "content": f"u{i}"}
+        session.messages.append(msg)
+        all_messages.append(msg)
+    for i in range(10):
+        msg = {"role": "assistant", "content": f"a{i}"}
+        session.messages.append(msg)
+        all_messages.append(msg)
+
+    archive_fn = MagicMock()
+    session.enforce_file_cap(on_archive=archive_fn, limit=6)
+
+    # Collect all messages accounted for (retained + archived)
+    accounted = set(id(m) for m in session.messages)
+    if archive_fn.called:
+        for m in archive_fn.call_args.args[0]:
+            accounted.add(id(m))
+
+    all_ids = set(id(m) for m in all_messages)
+    missing = all_ids - accounted
+    assert not missing, (
+        f"Lost {len(missing)} message(s) — neither retained nor archived"
+    )