From 91ba66db9ee7d4aea0dde5dff125d1a524293934 Mon Sep 17 00:00:00 2001
From: moe-berri <moe@berri.ai>
Date: Mon, 14 Sep 2026 14:25:31 -0700
Subject: [PATCH] fix(memory): retain duplicate directive cache positions

---
 litellm/proxy/memory/continuation.py          | 17 +++++++-------
 .../proxy/memory/test_memory_v2_boundaries.py | 23 +++++++++++++++++++
 2 files changed, 32 insertions(+), 8 deletions(-)

diff --git a/litellm/proxy/memory/continuation.py b/litellm/proxy/memory/continuation.py
index c916b76c532..8cd6e0ea49e 100644
--- a/litellm/proxy/memory/continuation.py
+++ b/litellm/proxy/memory/continuation.py
@@ -179,16 +179,17 @@ class MemoryContinuations:
             prefix: Final = result[: -(patch.replaces - 1)] if patch.replaces > 1 else result
             # Clients move cache breakpoints between turns. Reuse their current
             # directives rather than restoring an obsolete cached copy.
-            directives: Final = MappingProxyType(
-                {
-                    prefix_hashes((item,), self.route)[0]: item
-                    for item in items[index + 1 - patch.replaces : index + 1]
-                    if item.get("role") == "system"
-                }
+            current_directives: Final = tuple(
+                item for item in items[index + 1 - patch.replaces : index + 1] if item.get("role") == "system"
             )
+            positions: Final = tuple(
+                position for position, item in enumerate(patch.replacement) if item.get("role") == "system"
+            )
+            if len(positions) != len(current_directives):
+                raise HTTPException(status_code=409, detail="Invalid memory continuation directives")
+            directives: Final = MappingProxyType(dict(zip(positions, current_directives)))
             replacement: Final = tuple(
-                directives.get(prefix_hashes((item,), self.route)[0], item) if item.get("role") == "system" else item
-                for item in patch.replacement
+                directives.get(position, item) for position, item in enumerate(patch.replacement)
             )
             return _append_items(prefix, replacement, self.route)
 
diff --git a/tests/test_litellm/proxy/memory/test_memory_v2_boundaries.py b/tests/test_litellm/proxy/memory/test_memory_v2_boundaries.py
index 650c71939e5..64d0a2be176 100644
--- a/tests/test_litellm/proxy/memory/test_memory_v2_boundaries.py
+++ b/tests/test_litellm/proxy/memory/test_memory_v2_boundaries.py
@@ -655,6 +655,29 @@ async def test_claude_output_directives_reach_search_answer_and_reflection_round
     assert sum(message["role"] == "system" for message in object_items(loop.data.get("messages"))) == 1
 
 
+@pytest.mark.asyncio
+async def test_duplicate_directives_preserve_each_current_cache_breakpoint(prisma_edge: MagicMock) -> None:
+    first = {"role": "system", "content": [{"type": "text", "text": "Same directive"}]}
+    second = {
+        "role": "system",
+        "content": [{"type": "text", "text": "Same directive", "cache_control": {"type": "ephemeral"}}],
+    }
+    assistant = {"role": "assistant", "content": [{"type": "text", "text": "Reply"}]}
+    items = (first, second, assistant)
+    continuations = MemoryContinuations(store(prisma_edge), "anthropic_messages")
+    patch = MemoryContinuation(
+        replaces=3, replacement=({"role": "user", "content": "Memory reference"}, second, first, assistant)
+    )
+    prisma_edge.db.litellm_memorycontinuation.find_many.return_value = [
+        SimpleNamespace(
+            id=continuations.identifier(prefix_hashes(items, "anthropic_messages")[-1]), payload=patch.model_dump()
+        )
+    ]
+    restored = await continuations.restore(items)
+    assert restored[1:3] == (first, second)
+    assert restored[-1] == assistant
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize("bad_id,count", [(True, 1), (False, 17)])
 async def test_invalid_model_calls_are_rejected_before_storage(