diff --git a/litellm/llms/anthropic/experimental_pass_through/messages/mid_conversation_system.py b/litellm/llms/anthropic/experimental_pass_through/messages/mid_conversation_system.py
index c4fd7bcd320..ddefec6bac9 100644
--- a/litellm/llms/anthropic/experimental_pass_through/messages/mid_conversation_system.py
+++ b/litellm/llms/anthropic/experimental_pass_through/messages/mid_conversation_system.py
@@ -1,4 +1,5 @@
 from collections.abc import Mapping, Sequence
+from itertools import groupby
 from typing import Final
 
 CONVERTED_SYSTEM_NOTE: Final = (
@@ -39,39 +40,31 @@ def opens_with_tool_results(message: object) -> bool:
     )
 
 
-def system_run_before(messages: Sequence[Mapping[str, object]], index: int) -> Sequence[Mapping[str, object]]:
-    start: Final = next(
-        (j + 1 for j in range(index - 1, -1, -1) if not is_system_role_message(messages[j])),
-        0,
-    )
-    return messages[start:index]
-
-
-def system_run_end(messages: Sequence[Mapping[str, object]], index: int) -> int:
-    return next(
-        (j for j in range(index, len(messages)) if not is_system_role_message(messages[j])),
-        len(messages),
-    )
-
-
-def reordered_around_tool_results(
-    messages: Sequence[Mapping[str, object]], index: int
+def system_run_placed_after_tool_results(
+    system_run: Sequence[Mapping[str, object]], follower_run: Sequence[Mapping[str, object]]
 ) -> tuple[Mapping[str, object], ...]:
-    message: Final = messages[index]
-    if opens_with_tool_results(message):
-        return (message, *system_run_before(messages, index))
-    if not is_system_role_message(message):
-        return (message,)
-    run_end: Final = system_run_end(messages, index)
-    follower: Final = messages[run_end] if run_end < len(messages) else None
-    return () if opens_with_tool_results(follower) else (message,)
+    if follower_run and opens_with_tool_results(follower_run[0]):
+        return (follower_run[0], *system_run, *follower_run[1:])
+    return (*system_run, *follower_run)
 
 
 def system_turns_after_tool_results(
     messages: Sequence[Mapping[str, object]],
 ) -> tuple[Mapping[str, object], ...]:
-    return tuple(
-        message for index in range(len(messages)) for message in reordered_around_tool_results(messages, index)
+    runs: Final = tuple(tuple(run) for _, run in groupby(messages, key=is_system_role_message))
+    if not runs:
+        return ()
+    first_system_run: Final = 0 if is_system_role_message(runs[0][0]) else 1
+    paired_runs: Final = tuple(
+        (runs[i], runs[i + 1] if i + 1 < len(runs) else ()) for i in range(first_system_run, len(runs), 2)
+    )
+    return (
+        *(runs[0] if first_system_run else ()),
+        *(
+            m
+            for system_run, follower_run in paired_runs
+            for m in system_run_placed_after_tool_results(system_run, follower_run)
+        ),
     )
 
 
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mid_conversation_system.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mid_conversation_system.py
index 776dbd98833..33f3f388995 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mid_conversation_system.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mid_conversation_system.py
@@ -1,3 +1,5 @@
+import time
+
 from litellm.llms.anthropic.experimental_pass_through.messages.mid_conversation_system import (
     CONVERTED_SYSTEM_NOTE,
     convert_mid_conversation_system_turns,
@@ -60,3 +62,19 @@ def test_convert_mid_conversation_system_turns_moves_system_after_tool_result():
     assert result[1] is tool_result
     assert result[2]["role"] == "user"
     assert result[2]["content"][0]["text"] == CONVERTED_SYSTEM_NOTE
+
+
+def test_convert_mid_conversation_system_turns_handles_long_system_run_in_linear_time():
+    system_run = [{"role": "system", "content": f"reminder {i}"} for i in range(20_000)]
+    tool_result = {
+        "role": "user",
+        "content": [{"type": "tool_result", "tool_use_id": "toolu_1", "content": "Rainy"}],
+    }
+
+    started = time.perf_counter()
+    result = convert_mid_conversation_system_turns([{"role": "user", "content": "hi"}, *system_run, tool_result])
+    elapsed = time.perf_counter() - started
+
+    assert elapsed < 5
+    assert result[1] is tool_result
+    assert [m["content"][1]["text"] for m in result[2:]] == [m["content"] for m in system_run]