diff --git a/litellm/integrations/anthropic_cache_control_hook.py b/litellm/integrations/anthropic_cache_control_hook.py
index c54b42bf0ca..9e95678af93 100644
--- a/litellm/integrations/anthropic_cache_control_hook.py
+++ b/litellm/integrations/anthropic_cache_control_hook.py
@@ -439,6 +439,7 @@ class AnthropicCacheControlHook(CustomPromptManagement):
         """
         used_blocks = AnthropicCacheControlHook.count_request_cache_breakpoints(messages)
 
+        taken: set[int] = set()
         limit_reached = False
         for point in points:
             if used_blocks >= max_blocks:
@@ -449,7 +450,9 @@ class AnthropicCacheControlHook(CustomPromptManagement):
                 type="ephemeral"
             )
 
-            for target_index in AnthropicCacheControlHook._resolve_target_indices(point=point, messages=messages):
+            for target_index in AnthropicCacheControlHook._resolve_target_indices(
+                point=point, messages=messages, taken=taken
+            ):
                 if used_blocks >= max_blocks:
                     limit_reached = True
                     break
@@ -463,6 +466,7 @@ class AnthropicCacheControlHook(CustomPromptManagement):
                 )
                 if AnthropicCacheControlHook._message_has_cache_control(messages[target_index]):
                     used_blocks += 1
+                    taken.add(target_index)
 
             if limit_reached:
                 break
@@ -477,9 +481,16 @@ class AnthropicCacheControlHook(CustomPromptManagement):
 
     @staticmethod
     def _resolve_target_indices(
-        point: CacheControlMessageInjectionPoint, messages: list[AllMessageValues]
+        point: CacheControlMessageInjectionPoint, messages: list[AllMessageValues], taken: set[int] | None = None
     ) -> list[int]:
-        """Resolve which message indices an injection point targets."""
+        """Resolve which message indices an injection point targets.
+
+        ``taken`` is the messages an earlier point in the same request already marked.
+        The walk goes past them: arriving on one, finding it marked and dropping the
+        point turns two configured breakpoints into one, and the four exist so that a
+        prefix which stops matching at one can still match at an earlier one.
+        """
+        already_marked: Final = taken or set()
         _targetted_index: Final[int | str | None] = point.get("index", None)
         targetted_index: int | None = None
         if isinstance(_targetted_index, str):
@@ -527,7 +538,7 @@ class AnthropicCacheControlHook(CustomPromptManagement):
         position = targetted_index
         while position >= 0:
             index = candidates[position]
-            if _message_accepts_cache_control(messages[index]):
+            if index not in already_marked and _message_accepts_cache_control(messages[index]):
                 return [index]
             position -= 1
         return []
diff --git a/tests/unit/integrations/test_anthropic_cache_control_hook.py b/tests/unit/integrations/test_anthropic_cache_control_hook.py
index c9af51e0392..ed0ef328fe4 100644
--- a/tests/unit/integrations/test_anthropic_cache_control_hook.py
+++ b/tests/unit/integrations/test_anthropic_cache_control_hook.py
@@ -4061,3 +4061,30 @@ async def test_anthropic_cache_control_hook_walks_back_off_a_thinking_only_turn(
         "content": [{"type": "text", "text": "a1", "cache_control": {"type": "ephemeral"}}],
     }
     assert marked[3] == {"role": "assistant", "content": [{"type": "thinking", "thinking": "t", "signature": "s"}]}
+
+
+@pytest.mark.asyncio
+async def test_anthropic_cache_control_hook_two_points_stay_two_breakpoints(monkeypatch: pytest.MonkeyPatch):
+    """
+    The second point walks past the message the first one marked. Arriving on it,
+    finding it marked and dropping the point turns two configured breakpoints into one,
+    and the four exist so a prefix that stops matching at one can match at an earlier one.
+    """
+    marked = await _marked_messages(
+        [
+            {"role": "user", "content": "open"},
+            {"role": "assistant", "content": "ack"},
+            {"role": "user", "content": ""},
+        ],
+        [{"location": "message", "index": -1}, {"location": "message", "index": -2}],
+        monkeypatch,
+    )
+
+    assert marked == [
+        {"role": "user", "content": [{"type": "text", "text": "open", "cache_control": {"type": "ephemeral"}}]},
+        {"role": "assistant", "content": [{"type": "text", "text": "ack", "cache_control": {"type": "ephemeral"}}]},
+        {
+            "role": "user",
+            "content": [{"type": "text", "text": "[System: Empty message content sanitised to satisfy protocol]"}],
+        },
+    ]