diff --git a/litellm/__init__.py b/litellm/__init__.py
index 8e5dd68a186..2eaab2ca9fb 100644
--- a/litellm/__init__.py
+++ b/litellm/__init__.py
@@ -219,6 +219,7 @@ bedrock_request_metadata_fields: Optional[Sequence[str]] = (
 store_audit_logs: bool | None = None
 skip_system_message_in_guardrail: bool = False
 skip_tool_message_in_guardrail: bool = False
+skip_assistant_message_in_guardrail: bool = False
 ### end of callbacks #############
 
 email: Optional[str] = (
diff --git a/litellm/llms/anthropic/chat/guardrail_translation/handler.py b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
index 6436cd832c7..d483fe8896c 100644
--- a/litellm/llms/anthropic/chat/guardrail_translation/handler.py
+++ b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
@@ -51,6 +51,7 @@ from litellm.llms.base_llm.guardrail_translation.utils import (
     anthropic_tool_name,
     anthropic_tool_names,
     effective_scan_only_tool_results_for_guardrail,
+    effective_skip_assistant_message_for_guardrail,
     effective_skip_system_message_for_guardrail,
     effective_skip_tool_message_for_guardrail,
     list_field,
@@ -832,6 +833,7 @@ class AnthropicMessagesHandler(BaseTranslation):
 
         skip_system: Final = effective_skip_system_message_for_guardrail(guardrail_to_apply)
         skip_tool: Final = effective_skip_tool_message_for_guardrail(guardrail_to_apply)
+        skip_assistant: Final = effective_skip_assistant_message_for_guardrail(guardrail_to_apply)
         scan_only_tool_results: Final = effective_scan_only_tool_results_for_guardrail(guardrail_to_apply)
 
         # The top-level prompt is translated on its own below so it can be hoisted in front of
@@ -867,6 +869,7 @@ class AnthropicMessagesHandler(BaseTranslation):
             scan_only_tool_results=scan_only_tool_results,
             skip_system=False,
             skip_tool=skip_tool,
+            skip_assistant=skip_assistant,
         )
         structured_messages: Final = [full_structured_messages[index] for index in scoped_message_indices]
 
@@ -892,6 +895,7 @@ class AnthropicMessagesHandler(BaseTranslation):
                 msg_idx=msg_idx,
                 skip_system_message=skip_system,
                 skip_tool_message=skip_tool,
+                skip_assistant_message=skip_assistant,
                 scan_only_tool_results=scan_only_tool_results,
             )
             for msg_idx, message in enumerate(messages)
@@ -1254,6 +1258,7 @@ class AnthropicMessagesHandler(BaseTranslation):
         skip_system_message: bool = False,
         skip_tool_message: bool = False,
         scan_only_tool_results: bool = False,
+        skip_assistant_message: bool = False,
     ) -> ExtractedInput:
         """Extract text content and images from a message.
 
@@ -1267,6 +1272,8 @@ class AnthropicMessagesHandler(BaseTranslation):
             return cls._extract_midturn_system_text(message=message, msg_idx=msg_idx)
         if skip_tool_message and role.lower() == "tool":
             return EMPTY_EXTRACTED_INPUT
+        if skip_assistant_message and role.lower() == "assistant":
+            return EMPTY_EXTRACTED_INPUT
 
         content: Final = message.get("content", None)
         if isinstance(content, str):
diff --git a/litellm/llms/base_llm/guardrail_translation/utils.py b/litellm/llms/base_llm/guardrail_translation/utils.py
index fb886e42780..b48f6ccfa05 100644
--- a/litellm/llms/base_llm/guardrail_translation/utils.py
+++ b/litellm/llms/base_llm/guardrail_translation/utils.py
@@ -216,6 +216,15 @@ def _message_role(message: AllMessageValues) -> str:
     return str((message or {}).get("role") or "").lower()
 
 
+def effective_skip_assistant_message_for_guardrail(guardrail_to_apply: object) -> bool:
+    per: Final = getattr(guardrail_to_apply, "skip_assistant_message_in_guardrail", None)
+    if isinstance(per, bool):
+        return per
+    import litellm
+
+    return litellm.skip_assistant_message_in_guardrail
+
+
 def openai_messages_without_system(
     messages: Sequence[AllMessageValues],
 ) -> tuple[AllMessageValues, ...]:
@@ -231,16 +240,21 @@ def openai_messages_without_tool(
 def filter_messages_by_skip_flags(
     guardrail_to_apply: object, messages: Sequence[AllMessageValues]
 ) -> tuple[tuple[AllMessageValues, ...], bool]:
-    system_filtered = (
+    system_filtered: Final = (
         openai_messages_without_system(messages)
         if effective_skip_system_message_for_guardrail(guardrail_to_apply)
         else tuple(messages)
     )
-    fully_filtered = (
+    tool_filtered: Final = (
         openai_messages_without_tool(system_filtered)
         if effective_skip_tool_message_for_guardrail(guardrail_to_apply)
         else system_filtered
     )
+    fully_filtered: Final = (
+        tuple(message for message in tool_filtered if _message_role(message) != "assistant")
+        if effective_skip_assistant_message_for_guardrail(guardrail_to_apply)
+        else tool_filtered
+    )
     return fully_filtered, len(fully_filtered) != len(messages)
 
 
@@ -254,11 +268,14 @@ def role_out_of_guardrail_scope(
     skip_system_message: bool,
     skip_tool_message: bool,
     scan_only_tool_results: bool = False,
+    skip_assistant_message: bool = False,
 ) -> bool:
     if skip_system_message and role == "system":
         return True
     if skip_tool_message and role == "tool":
         return True
+    if skip_assistant_message and role == "assistant":
+        return True
     return scan_only_tool_results and role not in ("tool", "function")
 
 
@@ -268,6 +285,7 @@ def scoped_structured_message_indices(
     scan_only_tool_results: bool,
     skip_system: bool,
     skip_tool: bool,
+    skip_assistant: bool = False,
 ) -> tuple[int, ...]:
     return tuple(
         index
@@ -276,6 +294,7 @@ def scoped_structured_message_indices(
             _message_role(message),
             skip_system_message=skip_system,
             skip_tool_message=skip_tool,
+            skip_assistant_message=skip_assistant,
             scan_only_tool_results=scan_only_tool_results,
         )
     )
diff --git a/litellm/llms/bedrock/passthrough/guardrail_translation/handler.py b/litellm/llms/bedrock/passthrough/guardrail_translation/handler.py
index 3514a5e6e5c..b9e633374f5 100644
--- a/litellm/llms/bedrock/passthrough/guardrail_translation/handler.py
+++ b/litellm/llms/bedrock/passthrough/guardrail_translation/handler.py
@@ -23,6 +23,7 @@ from litellm.llms.base_llm.guardrail_translation.base_translation import (
 )
 from litellm.llms.base_llm.guardrail_translation.utils import (
     effective_scan_only_tool_results_for_guardrail,
+    effective_skip_assistant_message_for_guardrail,
     effective_skip_system_message_for_guardrail,
     effective_skip_tool_message_for_guardrail,
     scoped_structured_message_indices,
@@ -238,6 +239,7 @@ def _extract_converse_texts(
     skip_system: bool,
     skip_tool: bool,
     scan_only_tool_results: bool = False,
+    skip_assistant: bool = False,
 ) -> tuple[list[str], list[_StringHolder]]:
     """
     Walk a Bedrock Converse request body and collect text content.
@@ -279,6 +281,8 @@ def _extract_converse_texts(
     for message in body.get("messages") or []:
         if not isinstance(message, dict):
             continue
+        if skip_assistant and "role" in message and message["role"] == "assistant":
+            continue
         for block in message.get("content") or []:
             if not isinstance(block, dict):
                 continue
@@ -307,11 +311,18 @@ class _Scope:
     skip_system: bool
     skip_tool: bool
     scan_only_tool_results: bool
+    skip_assistant: bool = False
 
 
 def _texts_applied_rows(body: Mapping[str, object], texts: Sequence[str], scope: _Scope) -> tuple[ConverseRow, ...]:
     rewritten: Final = _BODY_BY_REFERENCE.validate_python(json.loads(json.dumps(body)))
-    _, holders = _extract_converse_texts(rewritten, scope.skip_system, scope.skip_tool, scope.scan_only_tool_results)
+    _, holders = _extract_converse_texts(
+        rewritten,
+        scope.skip_system,
+        scope.skip_tool,
+        scope.scan_only_tool_results,
+        skip_assistant=scope.skip_assistant,
+    )
     _write_back_texts(texts, holders)
     request: Final = parse_converse_request(rewritten)
     return converse_rows(request, include_tool_calls=not scope.skip_tool) if request else ()
@@ -540,7 +551,13 @@ def _edits_drop_a_text_change(
     if len(guardrailed_texts) != len(texts):
         return True
     rewritten: Final = _BODY_BY_REFERENCE.validate_python(json.loads(json.dumps(body)))
-    _, holders = _extract_converse_texts(rewritten, scope.skip_system, scope.skip_tool, scope.scan_only_tool_results)
+    _, holders = _extract_converse_texts(
+        rewritten,
+        scope.skip_system,
+        scope.skip_tool,
+        scope.scan_only_tool_results,
+        skip_assistant=scope.skip_assistant,
+    )
     writes: Final = _holder_edits(rewritten, edits, frozenset())
     if writes is None:
         return True
@@ -1391,12 +1408,14 @@ class BedrockPassthroughGuardrailHandler(BaseTranslation):
             skip_system=effective_skip_system_message_for_guardrail(guardrail_to_apply),
             skip_tool=effective_skip_tool_message_for_guardrail(guardrail_to_apply),
             scan_only_tool_results=effective_scan_only_tool_results_for_guardrail(guardrail_to_apply),
+            skip_assistant=effective_skip_assistant_message_for_guardrail(guardrail_to_apply),
         )
         texts, holders = _extract_converse_texts(
             request_body,
             scope.skip_system,
             scope.skip_tool,
             scope.scan_only_tool_results,
+            skip_assistant=scope.skip_assistant,
         )
         request: Final = parse_converse_request(request_body) if reads_rows else None
         rows: Final = converse_rows(request, include_tool_calls=not scope.skip_tool) if request else ()
@@ -1405,6 +1424,7 @@ class BedrockPassthroughGuardrailHandler(BaseTranslation):
             scan_only_tool_results=scope.scan_only_tool_results,
             skip_system=scope.skip_system,
             skip_tool=scope.skip_tool,
+            skip_assistant=scope.skip_assistant,
         )
 
         if not texts and not scoped_indices:
diff --git a/litellm/llms/openai/chat/guardrail_translation/handler.py b/litellm/llms/openai/chat/guardrail_translation/handler.py
index 5c5204ef2f4..079bcf43bd4 100644
--- a/litellm/llms/openai/chat/guardrail_translation/handler.py
+++ b/litellm/llms/openai/chat/guardrail_translation/handler.py
@@ -37,6 +37,7 @@ from litellm.llms.base_llm.guardrail_translation.base_translation import (
 from litellm.llms.base_llm.guardrail_translation.utils import (
     blocked_chat_stream_usage,
     effective_scan_only_tool_results_for_guardrail,
+    effective_skip_assistant_message_for_guardrail,
     effective_skip_system_message_for_guardrail,
     effective_skip_tool_message_for_guardrail,
     list_field,
@@ -116,6 +117,7 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
 
         skip_system: Final = effective_skip_system_message_for_guardrail(guardrail_to_apply)
         skip_tool: Final = effective_skip_tool_message_for_guardrail(guardrail_to_apply)
+        skip_assistant: Final = effective_skip_assistant_message_for_guardrail(guardrail_to_apply)
         scan_only_tool_results: Final = effective_scan_only_tool_results_for_guardrail(guardrail_to_apply)
 
         texts_to_check: Final[list[str]] = []
@@ -136,6 +138,7 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
                 tool_call_task_mappings=tool_call_task_mappings,
                 skip_system_message=skip_system,
                 skip_tool_message=skip_tool,
+                skip_assistant_message=skip_assistant,
                 scan_only_tool_results=scan_only_tool_results,
             )
 
@@ -152,6 +155,7 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
                 scan_only_tool_results=scan_only_tool_results,
                 skip_system=skip_system,
                 skip_tool=skip_tool,
+                skip_assistant=skip_assistant,
             )
             if structured_messages:
                 inputs["structured_messages"] = [structured_messages[index] for index in scoped_message_indices]
@@ -285,6 +289,7 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
         skip_system_message: bool = False,
         skip_tool_message: bool = False,
         scan_only_tool_results: bool = False,
+        skip_assistant_message: bool = False,
     ) -> None:
         """
         Extract text content, images, and tool calls from a message.
@@ -295,6 +300,7 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
             str(message.get("role") or "").lower(),
             skip_system_message=skip_system_message,
             skip_tool_message=skip_tool_message,
+            skip_assistant_message=skip_assistant_message,
             scan_only_tool_results=scan_only_tool_results,
         ):
             return
diff --git a/litellm/proxy/_lazy_openapi_snapshot.json b/litellm/proxy/_lazy_openapi_snapshot.json
index 5cb63c98d56..fe64a347318 100644
--- a/litellm/proxy/_lazy_openapi_snapshot.json
+++ b/litellm/proxy/_lazy_openapi_snapshot.json
@@ -16749,6 +16749,18 @@
               "description": "Minimum severity to block (high, medium, low)",
               "title": "Severity Threshold"
             },
+            "skip_assistant_message_in_guardrail": {
+              "anyOf": [
+                {
+                  "type": "boolean"
+                },
+                {
+                  "type": "null"
+                }
+              ],
+              "description": "When True, skip assistant-role messages in request history when building guardrail evaluation inputs. When False, include them even if the global litellm.skip_assistant_message_in_guardrail setting is True. When None, inherit the global setting. Does not skip checks on newly generated responses.",
+              "title": "Skip Assistant Message In Guardrail"
+            },
             "skip_system_message_in_guardrail": {
               "anyOf": [
                 {
@@ -19870,6 +19882,18 @@
               "description": "The Singulr Guardrail ID. Get guardrail ID from Singulr Platform.",
               "title": "Singulr Guardrail Id"
             },
+            "skip_assistant_message_in_guardrail": {
+              "anyOf": [
+                {
+                  "type": "boolean"
+                },
+                {
+                  "type": "null"
+                }
+              ],
+              "description": "When True, skip assistant-role messages in request history when building guardrail evaluation inputs. When False, include them even if the global litellm.skip_assistant_message_in_guardrail setting is True. When None, inherit the global setting. Does not skip checks on newly generated responses.",
+              "title": "Skip Assistant Message In Guardrail"
+            },
             "skip_system_message_in_guardrail": {
               "anyOf": [
                 {
diff --git a/litellm/proxy/guardrails/guardrail_hooks/crowdstrike_aidr/crowdstrike_aidr.py b/litellm/proxy/guardrails/guardrail_hooks/crowdstrike_aidr/crowdstrike_aidr.py
index ee3a957f607..3052e98a8f2 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/crowdstrike_aidr/crowdstrike_aidr.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/crowdstrike_aidr/crowdstrike_aidr.py
@@ -14,6 +14,7 @@ from litellm.integrations.custom_guardrail import (
     log_guardrail_information,
 )
 from litellm.llms.base_llm.guardrail_translation.utils import (
+    effective_skip_assistant_message_for_guardrail,
     effective_skip_system_message_for_guardrail,
     effective_skip_tool_message_for_guardrail,
 )
@@ -469,7 +470,11 @@ class CrowdStrikeAIDRHandler(CustomGuardrail):
 
     @override
     def structured_messages_cover_full_request(self) -> bool:
-        return effective_skip_system_message_for_guardrail(self) or effective_skip_tool_message_for_guardrail(self)
+        return (
+            effective_skip_system_message_for_guardrail(self)
+            or effective_skip_tool_message_for_guardrail(self)
+            or effective_skip_assistant_message_for_guardrail(self)
+        )
 
     @override
     def supports_structured_messages(self) -> bool:
@@ -482,7 +487,7 @@ class CrowdStrikeAIDRHandler(CustomGuardrail):
         sent_indices: tuple[int, ...],
         request_data: dict[str, object],
     ) -> list[AllMessageValues] | None:
-        if effective_skip_system_message_for_guardrail(self) or effective_skip_tool_message_for_guardrail(self):
+        if self.structured_messages_cover_full_request():
             request_messages: Final = request_data.get("messages")
             full_messages = (
                 cast("list[AllMessageValues]", request_messages)
diff --git a/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py b/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py
index 3e5c54b4501..8e42818c4ee 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/lakera_ai_v2.py
@@ -16,10 +16,12 @@ from litellm.integrations.custom_guardrail import (
     CustomGuardrail,
 )
 from litellm.llms.base_llm.guardrail_translation.utils import (
+    effective_skip_assistant_message_for_guardrail,
     effective_skip_system_message_for_guardrail,
     effective_skip_tool_message_for_guardrail,
     filter_messages_by_skip_flags,
     merge_guardrailed_scoped_messages,
+    role_out_of_guardrail_scope,
 )
 from litellm.llms.custom_httpx.http_handler import (
     get_async_httpx_client,
@@ -106,14 +108,19 @@ def _pre_masking_scope_indices(
     on length and the caller's strict positional zip raises."""
     skip_system: Final = effective_skip_system_message_for_guardrail(guardrail)
     skip_tool: Final = effective_skip_tool_message_for_guardrail(guardrail)
+    skip_assistant: Final = effective_skip_assistant_message_for_guardrail(guardrail)
     return tuple(
         idx
         for idx, message in enumerate(messages)
         if isinstance(message, dict)
         and isinstance(message.get("content"), str)
         and message["content"]
-        and not (skip_system and str(message.get("role") or "").lower() == "system")
-        and not (skip_tool and str(message.get("role") or "").lower() == "tool")
+        and not role_out_of_guardrail_scope(
+            str(message.get("role") or "").lower(),
+            skip_system_message=skip_system,
+            skip_tool_message=skip_tool,
+            skip_assistant_message=skip_assistant,
+        )
     )
 
 
@@ -259,6 +266,7 @@ class LakeraAIGuardrail(CustomGuardrail):
         skip_system_message_in_guardrail: bool | None = None,
         skip_tool_message_in_guardrail: bool | None = None,
         advisory_system_message: str | None = None,
+        skip_assistant_message_in_guardrail: bool | None = None,
         **kwargs,
     ):
         """
@@ -295,6 +303,7 @@ class LakeraAIGuardrail(CustomGuardrail):
         self.dev_info: bool | None = dev_info
         self.skip_system_message_in_guardrail = skip_system_message_in_guardrail
         self.skip_tool_message_in_guardrail = skip_tool_message_in_guardrail
+        self.skip_assistant_message_in_guardrail = skip_assistant_message_in_guardrail
         self.on_flagged = on_flagged or "block"
         self.advisory_system_message = advisory_system_message
         kwargs.setdefault("supported_event_hooks", list(self.get_supported_event_hooks()))
diff --git a/litellm/proxy/guardrails/guardrail_initializers.py b/litellm/proxy/guardrails/guardrail_initializers.py
index ebf1d8560ed..653ec80ff95 100644
--- a/litellm/proxy/guardrails/guardrail_initializers.py
+++ b/litellm/proxy/guardrails/guardrail_initializers.py
@@ -87,6 +87,7 @@ def initialize_lakera_v2(litellm_params: LitellmParams, guardrail: Guardrail):
         on_flagged=litellm_params.on_flagged,
         skip_system_message_in_guardrail=litellm_params.skip_system_message_in_guardrail,
         skip_tool_message_in_guardrail=litellm_params.skip_tool_message_in_guardrail,
+        skip_assistant_message_in_guardrail=litellm_params.skip_assistant_message_in_guardrail,
         advisory_system_message=litellm_params.advisory_system_message,
         timeout=litellm_params.timeout,
     )
diff --git a/litellm/proxy/guardrails/guardrail_registry.py b/litellm/proxy/guardrails/guardrail_registry.py
index 24b30e65e2b..74749049fb1 100644
--- a/litellm/proxy/guardrails/guardrail_registry.py
+++ b/litellm/proxy/guardrails/guardrail_registry.py
@@ -652,6 +652,7 @@ def _configure_callback_scoping(
     for scoping_param in (
         "skip_system_message_in_guardrail",
         "skip_tool_message_in_guardrail",
+        "skip_assistant_message_in_guardrail",
         "scan_only_tool_results",
     ):
         setattr(custom_guardrail_callback, scoping_param, getattr(litellm_params, scoping_param, None))
diff --git a/litellm/types/guardrails.py b/litellm/types/guardrails.py
index 718a651bdee..09c0accf9b7 100644
--- a/litellm/types/guardrails.py
+++ b/litellm/types/guardrails.py
@@ -1093,6 +1093,16 @@ class BaseLitellmParams(ContentFilterConfigModel):  # works for new and patch up
         ),
     )
 
+    skip_assistant_message_in_guardrail: bool | None = Field(
+        default=None,
+        description=(
+            "When True, skip assistant-role messages in request history when building "
+            "guardrail evaluation inputs. When False, include them even if the global "
+            "litellm.skip_assistant_message_in_guardrail setting is True. When None, "
+            "inherit the global setting. Does not skip checks on newly generated responses."
+        ),
+    )
+
     scan_only_tool_results: bool | None = Field(
         default=None,
         description=(
diff --git a/tests/unit/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py b/tests/unit/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
index c2ee58b67ed..0b178d62fb4 100644
--- a/tests/unit/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
+++ b/tests/unit/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
@@ -8,7 +8,8 @@ with guardrail transformations, specifically testing edge cases with empty choic
 import json
 import logging
 import re
-from typing import Any, Literal, Optional, Final
+from copy import deepcopy
+from typing import Any, Final, Literal, Optional
 from unittest.mock import MagicMock, patch
 
 import pytest
@@ -24,6 +25,45 @@ from litellm.llms.anthropic.messages.adapters.transformation import truncate_too
 from litellm.types.utils import ChatCompletionMessageToolCall, GenericGuardrailAPIInputs
 
 
+@pytest.mark.parametrize("skip_assistant", [False, True])
+@pytest.mark.asyncio
+async def test_skip_assistant_keeps_tool_results_and_mask_writeback(skip_assistant: bool) -> None:
+    guardrail: Final = MockMaskingGuardrail()
+    guardrail.skip_assistant_message_in_guardrail = skip_assistant
+    data: Final = {
+        "model": "test-model",
+        "messages": [
+            {"role": "user", "content": "hello"},
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "text", "text": "previous reply"},
+                    {"type": "tool_use", "id": "call_1", "name": "search", "input": {"q": "old"}},
+                ],
+            },
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "call_1", "content": "tool result"},
+                    {"type": "text", "text": "prohibited correction"},
+                ],
+            },
+        ],
+    }
+    original_assistant: Final = deepcopy(data["messages"][1])
+
+    await AnthropicMessagesHandler().process_input_messages(data, guardrail)
+
+    assert guardrail.inputs is not None
+    assert ("previous reply" in guardrail.inputs["texts"]) is not skip_assistant
+    assert "tool result" in guardrail.inputs["texts"]
+    assert bool(guardrail.inputs.get("tool_calls")) is not skip_assistant
+    assert any(message["role"] == "assistant" for message in guardrail.inputs["structured_messages"]) is not skip_assistant
+    assert data["messages"][1] == original_assistant
+    assert data["messages"][2]["content"][0]["content"] == "tool result"
+    assert data["messages"][2]["content"][1]["text"] == "[MASKED]"
+
+
 class MockPassThroughGuardrail(CustomGuardrail):
     """Mock guardrail that passes through without blocking - for testing streaming fallback behavior"""
 
diff --git a/tests/unit/llms/bedrock/passthrough/guardrail_translation/test_handler.py b/tests/unit/llms/bedrock/passthrough/guardrail_translation/test_handler.py
index 1c0ce5a334a..c2b75f998ea 100644
--- a/tests/unit/llms/bedrock/passthrough/guardrail_translation/test_handler.py
+++ b/tests/unit/llms/bedrock/passthrough/guardrail_translation/test_handler.py
@@ -75,6 +75,7 @@ def _make_guardrail(apply_result: dict) -> MagicMock:
     g.apply_guardrail = AsyncMock(return_value=apply_result)
     g.skip_system_message_in_guardrail = False
     g.skip_tool_message_in_guardrail = False
+    g.skip_assistant_message_in_guardrail = False
     return g
 
 
@@ -1381,6 +1382,45 @@ class TestDeAnonymizeConverseStream:
         assert result is stream_bytes
 
 
+@pytest.mark.parametrize("endpoint", ["model/test/converse", "model/test/converse-stream"])
+@pytest.mark.asyncio
+async def test_skip_assistant_preserves_converse_history_and_masks_user(endpoint: str) -> None:
+    assistant: Final = {
+        "role": "assistant",
+        "content": [
+            {"text": "old reply"},
+            {
+                "toolUse": {
+                    "toolUseId": "t1",
+                    "name": "search",
+                    "input": {"q": "old"},
+                }
+            },
+        ],
+    }
+    data: Final = {
+        "endpoint": endpoint,
+        "data": {
+            "messages": [
+                assistant,
+                {"role": "user", "content": [{"text": "private"}]},
+            ]
+        },
+    }
+    original_assistant: Final = copy.deepcopy(assistant)
+    guardrail: Final = MagicMock()
+    guardrail.apply_guardrail = AsyncMock(return_value={"texts": ["[MASKED]"]})
+    guardrail.skip_system_message_in_guardrail = False
+    guardrail.skip_tool_message_in_guardrail = False
+    guardrail.skip_assistant_message_in_guardrail = True
+
+    await BedrockPassthroughGuardrailHandler().process_input_messages(data, guardrail)
+
+    assert guardrail.apply_guardrail.call_args.kwargs["inputs"]["texts"] == ["private"]
+    assert data["data"]["messages"][0] == original_assistant
+    assert data["data"]["messages"][1]["content"][0]["text"] == "[MASKED]"
+
+
 class _ScriptedGuardrail(CustomGuardrail):
     def __init__(
         self,
@@ -1739,6 +1779,41 @@ _CARD_TOOL_CALL = {"card": "4111", "tags": ["a"]}
 
 
 class TestConverseRowEditWriteBack:
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("split_rows", [False, True], ids=["same-user-row", "separate-user-rows"])
+    async def test_skip_assistant_keeps_complementary_rewrites_atomic(self, split_rows: bool) -> None:
+        assistant: Final = {"role": "assistant", "content": [{"text": "old reply"}]}
+        blocks: Final = [{"text": "card 4111"}, {"text": "name Alice"}]
+        users: Final = (
+            [{"role": "user", "content": [block]} for block in blocks]
+            if split_rows
+            else [{"role": "user", "content": blocks}]
+        )
+        data: Final = _converse_request({"messages": [assistant, *users]})
+        original: Final = copy.deepcopy(data)
+        guardrail: Final = _ScriptedGuardrail(
+            lambda inputs: {
+                **_with_structured_text(inputs, "Alice", "[NAME]"),
+                "texts": ["card [CARD]", "name Alice"],
+            }
+        )
+        guardrail.skip_assistant_message_in_guardrail = True
+
+        if split_rows:
+            with pytest.raises(UnappliableRequestRewrite):
+                await BedrockPassthroughGuardrailHandler().process_input_messages(data, guardrail)
+            assert data["data"] == original["data"]
+        else:
+            result: Final = await BedrockPassthroughGuardrailHandler().process_input_messages(data, guardrail)
+            assert result["data"]["messages"] == [
+                original["data"]["messages"][0],
+                {"role": "user", "content": [{"text": "card [CARD]"}, {"text": "name [NAME]"}]},
+            ]
+
+        assert data["data"]["messages"][0] == original["data"]["messages"][0]
+        assert guardrail.received[-1]["texts"] == ["card 4111", "name Alice"]
+        assert [row["role"] for row in guardrail.received[-1]["structured_messages"]] == ["user"] * len(users)
+
     @pytest.mark.asyncio
     async def test_row_mask_of_a_request_field_is_written_back_into_that_field(self):
         data = _profile_converse_data()
@@ -2829,9 +2904,11 @@ class TestConverseStreamGuardrailRelay:
             [f"Card: {_TEST_CARD}. More text here"],
         ]
 
+    @pytest.mark.parametrize("skip_assistant", [False, True])
     @pytest.mark.asyncio
-    async def test_stream_held_until_moderated_applies_masks_per_block(self, monkeypatch):
+    async def test_stream_held_until_moderated_applies_masks_per_block(self, monkeypatch, skip_assistant: bool):
         guardrail = _CardMaskingGuardrail()
+        guardrail.skip_assistant_message_in_guardrail = skip_assistant
 
         relayed = await _relay_through_post_call_guardrail(
             _card_stream(), guardrail, monkeypatch, holds_until_moderated=True
@@ -2848,6 +2925,7 @@ class TestConverseStreamGuardrailRelay:
             "messageStop",
         ]
         assert TestDeAnonymizeConverseStream._deltas_by_block(relayed, "text") == {0: "Card: ****.", 1: "Thanks!"}
+        assert guardrail.received_texts == [[f"Card: {_TEST_CARD}.", "Thanks!"]]
         assert relayed.endswith(b"".join(_card_stream()[3:]))
 
     @pytest.mark.parametrize(
diff --git a/tests/unit/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py b/tests/unit/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py
index 5d71cbe9afc..3d3e314865a 100644
--- a/tests/unit/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py
+++ b/tests/unit/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py
@@ -7,11 +7,12 @@ with guardrail transformations, including tool calls.
 
 import json
 from collections.abc import Mapping
-from typing import Any, Literal, Optional
+from copy import deepcopy
+from typing import Any, Final, Literal, Optional
 
 import pytest
 
-
+import litellm
 from litellm.integrations.custom_guardrail import CustomGuardrail
 from litellm.llms.base_llm.guardrail_translation.base_translation import StreamingScanKey
 from litellm.llms.openai.chat.guardrail_translation.handler import (
@@ -27,6 +28,68 @@ from litellm.types.utils import (
 )
 
 
+@pytest.mark.parametrize(
+    "global_skip,per_guardrail_skip,expected_skip",
+    [(False, None, False), (True, None, True), (False, True, True), (True, False, False)],
+)
+@pytest.mark.asyncio
+async def test_skip_assistant_preserves_history_and_scans_other_roles(
+    monkeypatch: pytest.MonkeyPatch,
+    global_skip: bool,
+    per_guardrail_skip: bool | None,
+    expected_skip: bool,
+) -> None:
+    monkeypatch.setattr(litellm, "skip_assistant_message_in_guardrail", global_skip, raising=False)
+    guardrail: Final = MockGuardrail()
+    guardrail.skip_assistant_message_in_guardrail = per_guardrail_skip
+    data: Final = {
+        "messages": [
+            {"role": "user", "content": "hello"},
+            {
+                "role": "assistant",
+                "content": "previous reply",
+                "tool_calls": [
+                    {"id": "call_1", "type": "function", "function": {"name": "f", "arguments": '{"q":"old"}'}}
+                ],
+            },
+            {"role": "tool", "content": "tool result", "tool_call_id": "call_1"},
+        ],
+    }
+    original_assistant: Final = deepcopy(data["messages"][1])
+
+    result: Final = await OpenAIChatCompletionsHandler().process_input_messages(data, guardrail)
+
+    assert guardrail.last_inputs is not None
+    assert guardrail.last_inputs["texts"] == (
+        ["hello", "tool result"] if expected_skip else ["hello", "previous reply", "tool result"]
+    )
+    assert [message["role"] for message in guardrail.last_inputs["structured_messages"]] == (
+        ["user", "tool"] if expected_skip else ["user", "assistant", "tool"]
+    )
+    assert guardrail.tool_calls_modified is not expected_skip
+    assert result["messages"][0]["content"] == "HELLO"
+    assert result["messages"][2]["content"] == "TOOL RESULT"
+    if expected_skip:
+        assert result["messages"][1] == original_assistant
+    else:
+        assert result["messages"][1]["content"] == "PREVIOUS REPLY"
+
+
+@pytest.mark.asyncio
+async def test_skip_assistant_history_does_not_skip_new_output() -> None:
+    guardrail: Final = MockGuardrail()
+    guardrail.skip_assistant_message_in_guardrail = True
+    handler: Final = OpenAIChatCompletionsHandler()
+    data: Final = {"messages": [{"role": "assistant", "content": "old reply"}]}
+
+    assert await handler.process_input_messages(data, guardrail) == data
+    assert guardrail.last_inputs is None
+
+    response: Final = ModelResponse(choices=[Choices(message=Message(role="assistant", content="new reply"))])
+    result: Final = await handler.process_output_response(response, guardrail)
+    assert result.choices[0].message.content == "NEW REPLY"
+
+
 class MockGuardrail(CustomGuardrail):
     """Mock guardrail for testing that transforms text and tool calls"""
 
diff --git a/tests/unit/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py b/tests/unit/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py
index 23288a6136f..54a2d0884fc 100644
--- a/tests/unit/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py
+++ b/tests/unit/proxy/guardrails/guardrail_hooks/test_lakera_ai_v2.py
@@ -5,8 +5,11 @@ PR checklist requires at least one test in tests/test_litellm/.
 Additional tests live in tests/guardrails_tests/test_lakera_v2.py.
 """
 
-import importlib, logging, os
+import importlib
+import logging
+import os
 from collections.abc import Mapping
+from copy import deepcopy
 from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -21,6 +24,7 @@ from litellm.llms.base_llm.guardrail_translation.utils import (
 from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.guardrails.guardrail_hooks.lakera_ai_v2 import (
     LakeraAIGuardrail,
+    _apply_redacted_messages_back_preserving_fields,
     _build_lakera_inspection_messages,
     humanize_lakera_block_reasons,
 )
@@ -29,6 +33,23 @@ from litellm.types.utils import ModelResponse
 from tests._vcr_conftest_common import install_live_call_probe, record_vcr_outcome
 
 
+def test_skip_assistant_filters_inspection_and_preserves_masking_positions() -> None:
+    guardrail: Final = LakeraAIGuardrail(api_key="test_key", skip_assistant_message_in_guardrail=True)
+    messages: Final = [
+        {"role": "assistant", "content": "old reply", "name": "helper"},
+        {"role": "user", "content": "private"},
+    ]
+    original_assistant: Final = deepcopy(messages[0])
+    filtered, was_skipped = guardrail._filter_skipped_messages(messages)
+    assert filtered == (messages[1],)
+    assert was_skipped is True
+    data: Final = {"messages": messages}
+
+    _apply_redacted_messages_back_preserving_fields(guardrail, data, [{"role": "user", "content": "[MASKED]"}])
+
+    assert data["messages"] == [original_assistant, {"role": "user", "content": "[MASKED]"}]
+
+
 @pytest.mark.asyncio
 async def test_lakera_post_call_success_hook_returns_model_response_when_pii_masked():
     """
diff --git a/ui/litellm-dashboard/src/lib/http/schema.d.ts b/ui/litellm-dashboard/src/lib/http/schema.d.ts
index 2272b4bea43..5c587ab8e30 100644
--- a/ui/litellm-dashboard/src/lib/http/schema.d.ts
+++ b/ui/litellm-dashboard/src/lib/http/schema.d.ts
@@ -28138,6 +28138,11 @@ export interface components {
              * @description Minimum severity to block (high, medium, low)
              */
             severity_threshold?: string | null;
+            /**
+             * Skip Assistant Message In Guardrail
+             * @description When True, skip assistant-role messages in request history when building guardrail evaluation inputs. When False, include them even if the global litellm.skip_assistant_message_in_guardrail setting is True. When None, inherit the global setting. Does not skip checks on newly generated responses.
+             */
+            skip_assistant_message_in_guardrail?: boolean | null;
             /**
              * Skip System Message In Guardrail
              * @description When True, unified guardrails skip system-role messages when building evaluation inputs (texts and structured_messages). When False, system messages are included even if litellm_settings sets a global skip. When None, use the global litellm.skip_system_message_in_guardrail setting. For Anthropic /v1/messages, the flag applies only to the trusted top-level system prompt. In-sequence system entries are untrusted client input and remain in texts and structured_messages.
@@ -38430,6 +38435,11 @@ export interface components {
              * @description The Singulr Guardrail ID. Get guardrail ID from Singulr Platform.
              */
             singulr_guardrail_id?: string | null;
+            /**
+             * Skip Assistant Message In Guardrail
+             * @description When True, skip assistant-role messages in request history when building guardrail evaluation inputs. When False, include them even if the global litellm.skip_assistant_message_in_guardrail setting is True. When None, inherit the global setting. Does not skip checks on newly generated responses.
+             */
+            skip_assistant_message_in_guardrail?: boolean | null;
             /**
              * Skip System Message In Guardrail
              * @description When True, unified guardrails skip system-role messages when building evaluation inputs (texts and structured_messages). When False, system messages are included even if litellm_settings sets a global skip. When None, use the global litellm.skip_system_message_in_guardrail setting. For Anthropic /v1/messages, the flag applies only to the trusted top-level system prompt. In-sequence system entries are untrusted client input and remain in texts and structured_messages.