diff --git a/litellm/litellm_core_utils/prompt_templates/common_utils.py b/litellm/litellm_core_utils/prompt_templates/common_utils.py
index aa2e07234d..739c3119cc 100644
--- a/litellm/litellm_core_utils/prompt_templates/common_utils.py
+++ b/litellm/litellm_core_utils/prompt_templates/common_utils.py
@@ -257,6 +257,15 @@ def detect_first_expected_role(
     return None
 
 
+def _counts_for_alternation(message: AllMessageValues) -> bool:
+    role = message.get("role")
+    if role == "user":
+        return True
+    if role == "assistant":
+        return not bool(message.get("tool_calls"))
+    return False
+
+
 def _insert_user_continue_message(
     messages: List[AllMessageValues],
     user_continue_message: Optional[ChatCompletionUserMessage],
@@ -275,14 +284,6 @@ def _insert_user_continue_message(
     if not messages:
         return messages
 
-    def _counts_for_alternation(message: AllMessageValues) -> bool:
-        role = message.get("role")
-        if role == "user":
-            return True
-        if role == "assistant":
-            return not bool(message.get("tool_calls"))
-        return False
-
     result_messages = messages.copy()  # Don't modify the input list
     continue_message = user_continue_message or DEFAULT_USER_CONTINUE_MESSAGE
 
@@ -346,37 +347,33 @@ def _insert_assistant_continue_message(
     """
     if not ensure_alternating_roles or len(messages) <= 1:
         return messages
-
-    def _counts_for_alternation(message: AllMessageValues) -> bool:
-        role = message.get("role")
-        if role == "user":
-            return True
-        if role == "assistant":
-            return not bool(message.get("tool_calls"))
-        return False
-
-    # Create a new list to store modified messages
-    modified_messages: List[AllMessageValues] = []
+    continue_message = assistant_continue_message or DEFAULT_ASSISTANT_CONTINUE_MESSAGE
+    insert_before_indexes = set()
 
     for i, message in enumerate(messages):
+        if message.get("role") != "user":
+            continue
+
+        next_counted_index = i + 1
+        while next_counted_index < len(messages) and not _counts_for_alternation(
+            messages[next_counted_index]
+        ):
+            next_counted_index += 1
+
+        if (
+            next_counted_index < len(messages)
+            and messages[next_counted_index].get("role") == "user"
+        ):
+            # Insert before the next counted user turn.
+            # This avoids splitting assistant tool-call -> tool chains.
+            insert_before_indexes.add(next_counted_index)
+
+    modified_messages: List[AllMessageValues] = []
+    for idx, message in enumerate(messages):
+        if idx in insert_before_indexes:
+            modified_messages.append(continue_message)
         modified_messages.append(message)
 
-        if message.get("role") == "user" and _counts_for_alternation(message):
-            next_counted_index = i + 1
-            while next_counted_index < len(messages) and not _counts_for_alternation(
-                messages[next_counted_index]
-            ):
-                next_counted_index += 1
-
-            if (
-                next_counted_index < len(messages)
-                and messages[next_counted_index].get("role") == "user"
-            ):
-                continue_message = (
-                    assistant_continue_message or DEFAULT_ASSISTANT_CONTINUE_MESSAGE
-                )
-                modified_messages.append(continue_message)
-
     return modified_messages
 
 
diff --git a/tests/llm_translation/test_prompt_factory.py b/tests/llm_translation/test_prompt_factory.py
index 12efb47e06..355c23ae17 100644
--- a/tests/llm_translation/test_prompt_factory.py
+++ b/tests/llm_translation/test_prompt_factory.py
@@ -858,6 +858,50 @@ def test_ensure_alternating_roles_three_consecutive_assistants():
     ]
 
 
+def test_ensure_alternating_roles_does_not_split_tool_call_chain():
+    messages = [
+        {"role": "user", "content": "Search for X"},
+        {
+            "role": "assistant",
+            "content": None,
+            "tool_calls": [
+                {
+                    "id": "c1",
+                    "type": "function",
+                    "function": {"name": "search", "arguments": "{}"},
+                }
+            ],
+        },
+        {"role": "tool", "tool_call_id": "c1", "content": "results"},
+        {"role": "user", "content": "Thanks, now do Y"},
+    ]
+
+    transformed_messages = get_completion_messages(
+        messages=messages,
+        assistant_continue_message=None,
+        user_continue_message=None,
+        ensure_alternating_roles=True,
+    )
+
+    assert transformed_messages == [
+        {"role": "user", "content": "Search for X"},
+        {
+            "role": "assistant",
+            "content": None,
+            "tool_calls": [
+                {
+                    "id": "c1",
+                    "type": "function",
+                    "function": {"name": "search", "arguments": "{}"},
+                }
+            ],
+        },
+        {"role": "tool", "tool_call_id": "c1", "content": "results"},
+        {"role": "assistant", "content": "Please continue."},
+        {"role": "user", "content": "Thanks, now do Y"},
+    ]
+
+
 def test_alternating_roles_e2e():
     from litellm.llms.custom_httpx.http_handler import HTTPHandler
     import json