diff --git a/litellm/llms/bedrock/chat/converse_transformation.py b/litellm/llms/bedrock/chat/converse_transformation.py
index 03fbc35a97f..5281e6ae670 100644
--- a/litellm/llms/bedrock/chat/converse_transformation.py
+++ b/litellm/llms/bedrock/chat/converse_transformation.py
@@ -77,6 +77,7 @@ from litellm.llms.bedrock.common_utils import (
     bedrock_model_supports_regex_lookaround,
     bedrock_native_output_format,
     bedrock_native_output_is_opt_in,
+    bedrock_native_output_retry_requested,
     bedrock_supports_tool_search,
     deployment_model_info,
     requests_output_config_format,
@@ -1425,6 +1426,16 @@ class AmazonConverseConfig(BaseConfig):
             deployment_model_info(litellm_params),
         )
 
+    def uses_native_output(
+        self, model: str, optional_params: Mapping[str, object], litellm_params: Mapping[str, object]
+    ) -> bool:
+        return bedrock_native_output_retry_requested(
+            bedrock_capability_model(model, litellm_params.get("base_model")),
+            optional_params,
+            self.custom_llm_provider or "bedrock_converse",
+            deployment_model_info(litellm_params),
+        )
+
     def update_optional_params_with_thinking_tokens(self, non_default_params: dict, optional_params: dict):
         """
         Handles scenario where max tokens is not specified. For anthropic models (anthropic api/bedrock/vertex ai), this requires having the max tokens being set and being greater than the thinking token budget.
diff --git a/litellm/llms/bedrock/chat/invoke_transformations/anthropic_claude_transformation.py b/litellm/llms/bedrock/chat/invoke_transformations/anthropic_claude_transformation.py
index 62e1bee5217..1c38642e062 100644
--- a/litellm/llms/bedrock/chat/invoke_transformations/anthropic_claude_transformation.py
+++ b/litellm/llms/bedrock/chat/invoke_transformations/anthropic_claude_transformation.py
@@ -34,6 +34,7 @@ from litellm.llms.bedrock.common_utils import (
     bedrock_capability_model,
     bedrock_chat_uses_native_structured_output,
     bedrock_cleaned_output_schema,
+    bedrock_native_output_retry_requested,
     bedrock_supports_tool_search,
     deployment_model_info,
     get_anthropic_beta_from_headers,
@@ -161,6 +162,13 @@ class AmazonAnthropicClaudeConfig(AmazonInvokeConfig, AnthropicConfig):
     ) -> bool:
         return requests_opt_in_native_output(model, optional_params, deployment_model_info(litellm_params))
 
+    def uses_native_output(
+        self, model: str, optional_params: Mapping[str, object], litellm_params: Mapping[str, object]
+    ) -> bool:
+        return bedrock_native_output_retry_requested(
+            model, optional_params, model_info=deployment_model_info(litellm_params)
+        )
+
     def map_openai_params(
         self,
         non_default_params: dict,
diff --git a/litellm/llms/bedrock/chat/native_output_fallback.py b/litellm/llms/bedrock/chat/native_output_fallback.py
index 8069c3cf7e7..79742d0810c 100644
--- a/litellm/llms/bedrock/chat/native_output_fallback.py
+++ b/litellm/llms/bedrock/chat/native_output_fallback.py
@@ -1,4 +1,5 @@
 from collections.abc import Callable, Coroutine
+from dataclasses import dataclass
 from functools import partial
 from typing import Final, TypeAlias
 
@@ -6,6 +7,7 @@ from litellm.llms.anthropic.common_utils import is_claude_strict_tools_rejection
 from litellm.llms.base_llm.chat.transformation import BaseLLMException
 from litellm.llms.bedrock.common_utils import (
     NativeOutputFallback,
+    bedrock_strict_tools_fallback,
     is_bedrock_native_output_rejection,
     warn_bedrock_native_output_rejected,
     warn_bedrock_strict_tools_dropped,
@@ -17,7 +19,15 @@ NativeOutputResponse: TypeAlias = ModelResponse | CustomStreamWrapper
 NativeOutputAttemptResult: TypeAlias = NativeOutputResponse | Coroutine[object, object, NativeOutputResponse]
 NativeOutputAttempt: TypeAlias = Callable[[NativeOutputFallback | None], NativeOutputAttemptResult]
 NativeOutputFallbackFactory: TypeAlias = Callable[[], NativeOutputFallback | None]
-_RetryFor: TypeAlias = Callable[[BaseLLMException], NativeOutputFallback | None]
+
+
+@dataclass(frozen=True, slots=True)
+class _SelectedFallback:
+    fallback: NativeOutputFallback
+    native_output_retry: bool
+
+
+_RetryFor: TypeAlias = Callable[[BaseLLMException], _SelectedFallback | None]
 
 
 def _native_output_retry(
@@ -47,17 +57,42 @@ def _fallback_for(
     fallback: NativeOutputFallbackFactory | None,
     strict_tools_fallback: NativeOutputFallbackFactory | None,
     model: str,
-) -> NativeOutputFallback | None:
+) -> _SelectedFallback | None:
     native_output_retry: Final = _native_output_retry(error, fallback, model)
     if native_output_retry is not None:
-        return native_output_retry
-    return _strict_tools_retry(error, strict_tools_fallback, model)
+        return _SelectedFallback(native_output_retry, native_output_retry=True)
+    strict_tools_retry: Final = _strict_tools_retry(error, strict_tools_fallback, model)
+    if strict_tools_retry is None:
+        return None
+    return _SelectedFallback(strict_tools_retry, native_output_retry=False)
+
+
+def _strict_tools_retry_after_native_output_retry(
+    error: BaseLLMException,
+    retry: _SelectedFallback,
+    strict_tools_fallback: NativeOutputFallbackFactory | None,
+    model: str,
+) -> NativeOutputFallback | None:
+    if (
+        not retry.native_output_retry
+        or strict_tools_fallback is None
+        or not is_claude_strict_tools_rejection(error.status_code, error.message)
+    ):
+        return None
+    composed_retry: Final = bedrock_strict_tools_fallback(
+        model, retry.fallback.optional_params, retry.fallback.litellm_params
+    )
+    if composed_retry is not None:
+        warn_bedrock_strict_tools_dropped(model)
+    return composed_retry
 
 
 async def _await_with_native_output_fallback(
     first_attempt: Coroutine[object, object, NativeOutputResponse],
     attempt: NativeOutputAttempt,
     retry_for: _RetryFor,
+    strict_tools_fallback: NativeOutputFallbackFactory | None,
+    model: str,
 ) -> NativeOutputResponse:
     try:
         return await first_attempt
@@ -65,8 +100,17 @@ async def _await_with_native_output_fallback(
         retry: Final = retry_for(error)
         if retry is None:
             raise
-        second_attempt: Final = attempt(retry)
-    return await second_attempt if isinstance(second_attempt, Coroutine) else second_attempt
+    try:
+        second_attempt: Final = attempt(retry.fallback)
+        return await second_attempt if isinstance(second_attempt, Coroutine) else second_attempt
+    except BaseLLMException as error:
+        composed_retry: Final = _strict_tools_retry_after_native_output_retry(
+            error, retry, strict_tools_fallback, model
+        )
+        if composed_retry is None:
+            raise
+    third_attempt: Final = attempt(composed_retry)
+    return await third_attempt if isinstance(third_attempt, Coroutine) else third_attempt
 
 
 def call_with_native_output_fallback(
@@ -86,7 +130,15 @@ def call_with_native_output_fallback(
         retry: Final = retry_for(error)
         if retry is None:
             raise
-        return attempt(retry)
+        try:
+            return attempt(retry.fallback)
+        except BaseLLMException as retry_error:
+            composed_retry: Final = _strict_tools_retry_after_native_output_retry(
+                retry_error, retry, strict_tools_fallback, model
+            )
+            if composed_retry is None:
+                raise
+            return attempt(composed_retry)
     if isinstance(first_attempt, Coroutine):
-        return _await_with_native_output_fallback(first_attempt, attempt, retry_for)
+        return _await_with_native_output_fallback(first_attempt, attempt, retry_for, strict_tools_fallback, model)
     return first_attempt
diff --git a/litellm/llms/bedrock/common_utils.py b/litellm/llms/bedrock/common_utils.py
index dfee28a7cc9..3385c89c3a7 100644
--- a/litellm/llms/bedrock/common_utils.py
+++ b/litellm/llms/bedrock/common_utils.py
@@ -292,6 +292,15 @@ def _bedrock_model_supports(model: str, key: str, custom_llm_provider: str = "be
     return supports_factory(model=model, custom_llm_provider=custom_llm_provider, key=key)
 
 
+def _bedrock_native_output_enabled(
+    model: str, custom_llm_provider: str, model_info: Mapping[str, object] | None
+) -> bool:
+    deployment_flag: Final = (model_info or {}).get("supports_native_structured_output")
+    if isinstance(deployment_flag, bool):
+        return deployment_flag
+    return _bedrock_model_supports(model, "supports_native_structured_output", custom_llm_provider)
+
+
 _DEPLOYMENT_MODEL_INFO: Final = TypeAdapter(dict[str, object])
 
 
@@ -312,9 +321,9 @@ def _bedrock_native_output_opt_in(
 def bedrock_supports_native_structured_output(
     model: str, custom_llm_provider: str = "bedrock", model_info: Mapping[str, object] | None = None
 ) -> bool:
-    return _bedrock_model_supports(
-        model, "supports_native_structured_output", custom_llm_provider
-    ) or _bedrock_native_output_opt_in(model, custom_llm_provider, model_info)
+    return _bedrock_native_output_enabled(model, custom_llm_provider, model_info) or _bedrock_native_output_opt_in(
+        model, custom_llm_provider, model_info
+    )
 
 
 def _bedrock_map_native_output_flag(model: str) -> object:
@@ -349,7 +358,7 @@ def bedrock_chat_opts_into_native_structured_output(
     custom_llm_provider: str = "bedrock",
     model_info: Mapping[str, object] | None = None,
 ) -> bool:
-    return _bedrock_model_supports(model, "supports_native_structured_output", custom_llm_provider) or (
+    return _bedrock_native_output_enabled(model, custom_llm_provider, model_info) or (
         thinking_requested and _bedrock_native_output_opt_in(model, custom_llm_provider, model_info)
     )
 
@@ -370,15 +379,15 @@ def bedrock_chat_uses_native_structured_output(
 def bedrock_native_output_is_deployment_opt_in(
     model: str, custom_llm_provider: str = "bedrock", model_info: Mapping[str, object] | None = None
 ) -> bool:
-    return not _bedrock_model_supports(
-        model, "supports_native_structured_output", custom_llm_provider
-    ) and _bedrock_native_output_opt_in(model, custom_llm_provider, model_info)
+    return not _bedrock_native_output_enabled(model, custom_llm_provider, model_info) and _bedrock_native_output_opt_in(
+        model, custom_llm_provider, model_info
+    )
 
 
 def bedrock_native_output_is_opt_in(
     model: str, custom_llm_provider: str = "bedrock", model_info: Mapping[str, object] | None = None
 ) -> bool:
-    return not _bedrock_model_supports(model, "supports_native_structured_output", custom_llm_provider) and (
+    return not _bedrock_native_output_enabled(model, custom_llm_provider, model_info) and (
         _bedrock_native_output_opt_in(model, custom_llm_provider, model_info)
         or _bedrock_native_output_replaces_unforceable_tool(model, model_info)
     )
@@ -387,7 +396,21 @@ def bedrock_native_output_is_opt_in(
 def without_bedrock_native_output_opt_in(litellm_params: Mapping[str, object]) -> Mapping[str, object]:
     return {
         **litellm_params,
-        "model_info": {**deployment_model_info(litellm_params), "supports_bedrock_native_structured_output": False},
+        "model_info": {
+            **deployment_model_info(litellm_params),
+            "supports_bedrock_native_structured_output": False,
+        },
+    }
+
+
+def for_bedrock_json_tool_retry(litellm_params: Mapping[str, object]) -> Mapping[str, object]:
+    opt_in_disabled: Final = without_bedrock_native_output_opt_in(litellm_params)
+    return {
+        **opt_in_disabled,
+        "model_info": {
+            **deployment_model_info(opt_in_disabled),
+            "supports_native_structured_output": False,
+        },
     }
 
 
@@ -395,6 +418,7 @@ _BEDROCK_NATIVE_OUTPUT_UNSUPPORTED: Final = "output_config.format: Extra inputs
 _BEDROCK_NATIVE_OUTPUT_REJECTIONS: Final = (
     _BEDROCK_NATIVE_OUTPUT_UNSUPPORTED,
     "compilation exceeded limits: Schema is too complex",
+    "The compiled grammar is too large",
     "output_config.format.schema:",
 )
 
@@ -475,8 +499,27 @@ def requests_output_config_format(optional_params: Mapping[str, object]) -> bool
 
 
 def requests_native_output(anthropic_optional_params: Mapping[str, object]) -> bool:
-    return isinstance(anthropic_optional_params.get("output_format"), Mapping) or requests_output_config_format(
-        anthropic_optional_params
+    output_config: Final = json_object_or_none(anthropic_optional_params.get("outputConfig"))
+    return (
+        isinstance(anthropic_optional_params.get("output_format"), Mapping)
+        or requests_output_config_format(anthropic_optional_params)
+        or (
+            anthropic_optional_params.get("json_mode") is True
+            and output_config is not None
+            and isinstance(output_config.get("textFormat"), Mapping)
+        )
+    )
+
+
+def bedrock_native_output_retry_requested(
+    model: str,
+    optional_params: Mapping[str, object],
+    custom_llm_provider: str = "bedrock",
+    model_info: Mapping[str, object] | None = None,
+) -> bool:
+    return requests_native_output(optional_params) and (
+        bedrock_native_output_is_opt_in(model, custom_llm_provider, model_info)
+        or _bedrock_native_output_enabled(model, custom_llm_provider, model_info)
     )
 
 
@@ -518,7 +561,7 @@ def bedrock_native_output_schema(
     model_info: Mapping[str, object] | None = None,
 ) -> Mapping[str, object] | None:
     native_schema: Final = bedrock_cleaned_output_schema(model, schema, custom_llm_provider)
-    if _bedrock_model_supports(model, "supports_native_structured_output", custom_llm_provider):
+    if _bedrock_native_output_enabled(model, custom_llm_provider, model_info):
         return schema if native_schema is None else native_schema
     if _bedrock_native_output_opt_in(model, custom_llm_provider, model_info):
         return native_schema
diff --git a/litellm/llms/bedrock/messages/invoke_transformations/anthropic_claude_transformation.py b/litellm/llms/bedrock/messages/invoke_transformations/anthropic_claude_transformation.py
index 8b4e2e5b5c5..51f37364245 100644
--- a/litellm/llms/bedrock/messages/invoke_transformations/anthropic_claude_transformation.py
+++ b/litellm/llms/bedrock/messages/invoke_transformations/anthropic_claude_transformation.py
@@ -40,15 +40,17 @@ from litellm.llms.bedrock.common_utils import (
     BEDROCK_INVOKE_CONTEXT_MANAGEMENT_EDIT_BETAS,
     BedrockError,
     apply_bedrock_invoke_structured_output,
-    bedrock_native_output_is_deployment_opt_in,
+    bedrock_native_output_format,
+    bedrock_native_output_retry_requested,
     bedrock_supports_tool_search,
     ensure_bedrock_anthropic_messages_tool_names,
+    for_bedrock_json_tool_retry,
     get_anthropic_beta_from_headers,
     is_bedrock_native_output_rejection,
+    json_object_or_none,
     normalize_bedrock_opus_output_config_effort,
     normalize_custom_field_on_tools,
     normalize_tool_input_schema_types_for_bedrock_invoke,
-    requests_native_output,
     requests_output_config_format,
     strip_unsupported_bedrock_invoke_output_config_keys,
     supports_bedrock_prompt_cache_ttl,
@@ -133,13 +135,24 @@ class AmazonAnthropicClaudeMessagesConfig(
     ) -> GenericLiteLLMParams | None:
         model_info: Final = _MODEL_INFO.validate_python(litellm_params.model_info)
         if not (
-            requests_native_output(anthropic_messages_optional_request_params)
-            and bedrock_native_output_is_deployment_opt_in(model, model_info=model_info)
+            bedrock_native_output_retry_requested(
+                model, anthropic_messages_optional_request_params, model_info=model_info
+            )
         ):
             return None
-        return litellm_params.model_copy(
-            update={"model_info": {**(model_info or {}), "supports_bedrock_native_structured_output": False}}
+        legacy_output_format: Final = json_object_or_none(
+            anthropic_messages_optional_request_params.get("output_format")
         )
+        output_config: Final = json_object_or_none(anthropic_messages_optional_request_params.get("output_config"))
+        output_config_format: Final = (
+            json_object_or_none(output_config.get("format")) if output_config is not None else None
+        )
+        output_format: Final = legacy_output_format if legacy_output_format is not None else output_config_format
+        if output_format is None or (bedrock_native_output_format(model, output_format, model_info=model_info) is None):
+            return None
+        retry_params: Final = for_bedrock_json_tool_retry({"model_info": model_info})
+        retry_model_info: Final = _MODEL_INFO.validate_python(retry_params.get("model_info"))
+        return litellm_params.model_copy(update={"model_info": retry_model_info})
 
     def should_retry_anthropic_messages_without_native_output(
         self, e: httpx.HTTPStatusError, request_body: Mapping[str, object], model: str
diff --git a/litellm/main.py b/litellm/main.py
index 8cb133bf76b..6b9964a450f 100644
--- a/litellm/main.py
+++ b/litellm/main.py
@@ -143,7 +143,7 @@ from litellm.llms.bedrock.common_utils import (
     bedrock_route_for_request,
     bedrock_strict_tools_fallback,
     deployment_model_info,
-    without_bedrock_native_output_opt_in,
+    for_bedrock_json_tool_retry,
     without_bedrock_route_prefix,
 )
 from litellm.llms.bedrock_mantle.chat.claude_transformation import bedrock_mantle_chat_config
@@ -4369,7 +4369,7 @@ def _native_output_fallback(
     first_attempt_params: Mapping[str, object],
     first_attempt_litellm_params: Mapping[str, object],
 ) -> NativeOutputFallback:
-    litellm_params: Final = without_bedrock_native_output_opt_in(first_attempt_litellm_params)
+    litellm_params: Final = for_bedrock_json_tool_retry(first_attempt_litellm_params)
     remapped_params: Final = ctx.optional_params_for_model_info(deployment_model_info(litellm_params))
     return NativeOutputFallback(
         optional_params={
@@ -4500,7 +4500,7 @@ def _complete_bedrock(ctx: CompletionDispatchContext) -> _CompletionDispatchResu
             converse_attempt,
             (
                 partial(_converse_native_output_fallback, ctx, converse_params, dict(litellm_params))
-                if AmazonConverseConfig().uses_opt_in_native_output(converse_model, converse_params, litellm_params)
+                if AmazonConverseConfig().uses_native_output(converse_model, converse_params, litellm_params)
                 else None
             ),
             converse_model,
@@ -4556,7 +4556,7 @@ def _complete_bedrock(ctx: CompletionDispatchContext) -> _CompletionDispatchResu
             (
                 partial(_native_output_fallback, ctx, invoke_params, dict(litellm_params))
                 if isinstance(provider_config, AmazonAnthropicClaudeConfig)
-                and provider_config.uses_opt_in_native_output(model, invoke_params, litellm_params)
+                and provider_config.uses_native_output(model, invoke_params, litellm_params)
                 else None
             ),
             model,
diff --git a/litellm/model_prices_and_context_window_backup.json b/litellm/model_prices_and_context_window_backup.json
index a29f97ee9ea..ad57685da04 100644
--- a/litellm/model_prices_and_context_window_backup.json
+++ b/litellm/model_prices_and_context_window_backup.json
@@ -2242,7 +2242,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2331,7 +2331,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2420,7 +2420,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2504,7 +2504,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2593,7 +2593,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2715,7 +2715,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2759,7 +2759,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2803,7 +2803,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2847,7 +2847,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2891,7 +2891,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -75504,7 +75504,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -75544,7 +75544,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
diff --git a/model_prices_and_context_window.json b/model_prices_and_context_window.json
index a29f97ee9ea..ad57685da04 100644
--- a/model_prices_and_context_window.json
+++ b/model_prices_and_context_window.json
@@ -2242,7 +2242,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2331,7 +2331,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2420,7 +2420,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2504,7 +2504,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2593,7 +2593,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
@@ -2715,7 +2715,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2759,7 +2759,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2803,7 +2803,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2847,7 +2847,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -2891,7 +2891,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -75504,7 +75504,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_bedrock_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
@@ -75544,7 +75544,7 @@
         "supports_tool_choice": true,
         "supports_vision": true,
         "supports_xhigh_reasoning_effort": true,
-        "supports_native_structured_output": false,
+        "supports_native_structured_output": true,
         "supports_max_reasoning_effort": true,
         "supports_output_config": true,
         "supports_parallel_tool_use_config": true,
diff --git a/tests/unit/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude_transformation.py b/tests/unit/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude_transformation.py
index 93f6e237fc7..053574d7dd6 100644
--- a/tests/unit/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude_transformation.py
+++ b/tests/unit/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude_transformation.py
@@ -2047,8 +2047,9 @@ def _invoke_chat_params(
 )
 @pytest.mark.parametrize("model", ["us.anthropic.claude-opus-4-8", "global.anthropic.claude-sonnet-5"])
 def test_invoke_uses_opt_in_native_output_when_the_opt_in_drove_native_output(
-    local_model_cost_map, model, thinking_params
+    local_model_cost_map, model, thinking_params, monkeypatch
 ):
+    monkeypatch.setitem(litellm.model_cost[model], "supports_native_structured_output", False)
     optional_params: Final = _invoke_chat_params(
         model, None, {"response_format": _CITY_RESPONSE_FORMAT, **thinking_params}
     )
@@ -2083,6 +2084,15 @@ def test_invoke_uses_opt_in_native_output_is_false_when_native_output_did_not_co
     )
 
 
+def test_invoke_uses_default_native_output_for_schema_retry(local_model_cost_map: None) -> None:
+    model: Final = "us.anthropic.claude-opus-5"
+    optional_params: Final = _invoke_chat_params(
+        model, None, {"response_format": _CITY_RESPONSE_FORMAT, "thinking": {"type": "disabled"}}
+    )
+
+    assert AmazonAnthropicClaudeConfig().uses_native_output(model, optional_params, {})
+
+
 @pytest.mark.parametrize(
     ("forced_tool_use", "map_flag", "model_info", "thinking_params", "native"),
     [
diff --git a/tests/unit/llms/bedrock/chat/test_converse_transformation.py b/tests/unit/llms/bedrock/chat/test_converse_transformation.py
index b8eb5858fda..b37d6977c10 100644
--- a/tests/unit/llms/bedrock/chat/test_converse_transformation.py
+++ b/tests/unit/llms/bedrock/chat/test_converse_transformation.py
@@ -5244,6 +5244,44 @@ def test_models_whose_thinking_stops_under_native_output_keep_the_json_tool_only
     assert ("toolConfig" in request) is not native
 
 
+@pytest.mark.usefixtures("local_model_cost_map")
+@pytest.mark.parametrize(
+    ("model", "thinking_params", "native"),
+    [
+        ("us.anthropic.claude-opus-5", None, True),
+        ("us.anthropic.claude-opus-5", {"thinking": {"type": "adaptive"}}, True),
+        ("us.anthropic.claude-opus-5", {"thinking": {"type": "disabled"}}, True),
+        ("us.anthropic.claude-opus-4-8", None, True),
+        ("us.anthropic.claude-opus-4-8", {"thinking": {"type": "adaptive"}}, True),
+        ("us.anthropic.claude-opus-4-8", {"thinking": {"type": "disabled"}}, True),
+        ("us-gov.anthropic.claude-opus-5", None, False),
+        ("us-gov.anthropic.claude-opus-4-8", None, False),
+    ],
+    ids=[
+        "opus-5-unset",
+        "opus-5-adaptive",
+        "opus-5-disabled",
+        "opus-4-8-unset",
+        "opus-4-8-adaptive",
+        "opus-4-8-disabled",
+        "opus-5-us-gov",
+        "opus-4-8-us-gov",
+    ],
+)
+def test_opus_5_and_4_8_cost_map_defaults_use_native_output_across_thinking_modes(
+    model: str, thinking_params: Mapping[str, object] | None, native: bool
+) -> None:
+    _, request = _converse_request_for_json_schema(model, False, thinking_params)
+
+    if native:
+        assert request["outputConfig"]["textFormat"]["type"] == "json_schema"
+        assert "toolConfig" not in request
+        return
+
+    assert "outputConfig" not in request
+    assert [tool["toolSpec"]["name"] for tool in request["toolConfig"]["tools"]] == ["json_tool_call"]
+
+
 def _converse_capital_answer(request: httpx.Request) -> httpx.Response:
     return httpx.Response(
         200,
@@ -11599,7 +11637,10 @@ _OUTPUT_CONFIG_FORMAT: Final = {
     ids=["adaptive", "reasoning_effort", "budget", "output_config_format"],
 )
 @pytest.mark.parametrize("model", ["us.anthropic.claude-opus-4-8", "global.anthropic.claude-sonnet-5"])
-def test_uses_opt_in_native_output_when_the_opt_in_drove_native_output(local_model_cost_map, model, request_params):
+def test_uses_opt_in_native_output_when_the_opt_in_drove_native_output(
+    local_model_cost_map, monkeypatch, model, request_params
+):
+    monkeypatch.setitem(litellm.model_cost[model], "supports_native_structured_output", False)
     optional_params: Final = _converse_params(model, None, request_params)
 
     assert AmazonConverseConfig().uses_opt_in_native_output(model, optional_params, {"model_info": {"id": "d1"}})
@@ -11630,7 +11671,10 @@ def test_uses_opt_in_native_output_is_false_when_native_output_did_not_come_from
     assert not AmazonConverseConfig().uses_opt_in_native_output(model, optional_params, {"model_info": model_info})
 
 
-def test_uses_opt_in_native_output_reads_the_base_model_of_an_application_inference_profile(local_model_cost_map):
+def test_uses_opt_in_native_output_reads_the_base_model_of_an_application_inference_profile(
+    local_model_cost_map, monkeypatch
+):
+    monkeypatch.setitem(litellm.model_cost["us.anthropic.claude-opus-4-8"], "supports_native_structured_output", False)
     profile: Final = "arn:aws:bedrock:us-east-1:000000000000:application-inference-profile/profile-id"
     litellm_params: Final = {"base_model": "bedrock/us.anthropic.claude-opus-4-8"}
     optional_params: Final = _converse_params(
@@ -11698,8 +11742,9 @@ _BEDROCK_SCHEMA_REFUSAL: Final = "output_config.format.schema: pattern is too co
 )
 @pytest.mark.respx(assert_all_called=True)
 def test_a_refused_native_schema_is_sent_again_only_when_the_retry_drops_native_output(
-    caller_params: dict, expected_calls: int, respx_mock: respx.Router, local_model_cost_map: None
+    caller_params: dict, expected_calls: int, respx_mock: respx.Router, local_model_cost_map: None, monkeypatch
 ) -> None:
+    monkeypatch.setitem(litellm.model_cost["us.anthropic.claude-opus-4-8"], "supports_native_structured_output", False)
     route: Final = respx_mock.post(url__regex=r"/converse$").mock(
         return_value=httpx.Response(400, json={"message": _BEDROCK_SCHEMA_REFUSAL})
     )
@@ -11722,6 +11767,61 @@ def test_a_refused_native_schema_is_sent_again_only_when_the_retry_drops_native_
     assert all("outputConfig" not in json.loads(call.request.content) for call in route.calls[1:])
 
 
+@pytest.mark.respx(assert_all_called=True)
+def test_a_default_native_schema_rejection_retries_with_the_json_tool(
+    respx_mock: respx.Router, local_model_cost_map: None
+) -> None:
+    route: Final = respx_mock.post(url__regex=r"/converse$").mock(
+        return_value=httpx.Response(400, json={"message": _BEDROCK_SCHEMA_REFUSAL})
+    )
+
+    with pytest.raises(litellm.BadRequestError, match=re.escape(_BEDROCK_SCHEMA_REFUSAL)):
+        completion(
+            model="bedrock/converse/us.anthropic.claude-opus-5",
+            messages=[{"role": "user", "content": "What is the capital of France?"}],
+            response_format=CAPITAL_RESPONSE_FORMAT,
+            thinking={"type": "disabled"},
+            num_retries=0,
+            aws_access_key_id="fake",
+            aws_secret_access_key="fake",
+            aws_region_name="us-east-1",
+            client=HTTPHandler(),
+        )
+
+    assert route.call_count == 2
+    first_request: Final = json.loads(route.calls[0].request.content)
+    retry_request: Final = json.loads(route.calls[1].request.content)
+    assert "outputConfig" in first_request and "toolConfig" not in first_request
+    assert "toolConfig" in retry_request and "outputConfig" not in retry_request
+
+
+@pytest.mark.respx(assert_all_called=True)
+def test_an_unforceable_tool_native_schema_rejection_retries_with_the_json_tool(
+    respx_mock: respx.Router, local_model_cost_map: None
+) -> None:
+    route: Final = respx_mock.post(url__regex=r"/converse$").mock(
+        return_value=httpx.Response(400, json={"message": _BEDROCK_SCHEMA_REFUSAL})
+    )
+
+    with pytest.raises(litellm.BadRequestError, match=re.escape(_BEDROCK_SCHEMA_REFUSAL)):
+        completion(
+            model="bedrock/converse/anthropic.claude-fable-5-1",
+            messages=[{"role": "user", "content": "What is the capital of France?"}],
+            response_format=CAPITAL_RESPONSE_FORMAT,
+            num_retries=0,
+            aws_access_key_id="fake",
+            aws_secret_access_key="fake",
+            aws_region_name="us-east-1",
+            client=HTTPHandler(),
+        )
+
+    assert route.call_count == 2
+    first_request: Final = json.loads(route.calls[0].request.content)
+    retry_request: Final = json.loads(route.calls[1].request.content)
+    assert "outputConfig" in first_request and "toolConfig" not in first_request
+    assert "toolConfig" in retry_request and "outputConfig" not in retry_request
+
+
 CONTROL_PLANE_ENDPOINT: Final = "https://bedrock-fips.us-east-1.amazonaws.com"
 
 
diff --git a/tests/unit/llms/bedrock/chat/test_invoke_handler.py b/tests/unit/llms/bedrock/chat/test_invoke_handler.py
index 4424f7640a3..2faa089e1c3 100644
--- a/tests/unit/llms/bedrock/chat/test_invoke_handler.py
+++ b/tests/unit/llms/bedrock/chat/test_invoke_handler.py
@@ -1214,7 +1214,7 @@ async def test_converse_json_schema_stream_sends_claude_prose_only_when_claude_s
 
     transport: Final = httpx.MockTransport(handle_request)
     request: Final = {
-        "model": "bedrock/us.anthropic.claude-opus-5",
+        "model": "bedrock/anthropic.claude-opus-5",
         "messages": [{"role": "user", "content": "What is the LCM of 24 and 120? Reply in JSON."}],
         "response_format": {
             "type": "json_schema",
diff --git a/tests/unit/llms/bedrock/chat/test_native_output_fallback.py b/tests/unit/llms/bedrock/chat/test_native_output_fallback.py
index 9ee8c14f5d6..81832d7d8bf 100644
--- a/tests/unit/llms/bedrock/chat/test_native_output_fallback.py
+++ b/tests/unit/llms/bedrock/chat/test_native_output_fallback.py
@@ -13,10 +13,33 @@ _MODEL: Final = "us.anthropic.claude-opus-4-8"
 _FALLBACK: Final = NativeOutputFallback(
     optional_params={"tools": "json_tool_call"}, litellm_params={"model_info": {"opted_out": True}}
 )
+_NATIVE_RETRY_WITH_STRICT_TOOLS: Final = NativeOutputFallback(
+    optional_params={
+        "tools": (
+            {"function": {"name": "json_schema", "strict": True}},
+            {"function": {"name": "custom", "strict": True}},
+        )
+    },
+    litellm_params={
+        "model_info": {
+            "supports_native_structured_output": False,
+            "supports_bedrock_native_structured_output": False,
+        }
+    },
+)
+_COMPOSED_FALLBACK: Final = NativeOutputFallback(
+    optional_params={"tools": [{"function": {"name": "json_schema"}}, {"function": {"name": "custom"}}]},
+    litellm_params=_NATIVE_RETRY_WITH_STRICT_TOOLS.litellm_params,
+)
 _REJECTION: Final = BedrockError(
     status_code=400,
     message='{"message":"The model returned the following errors: output_config.format: Extra inputs are not permitted"}',
 )
+_GRAMMAR_REJECTION: Final = BedrockError(
+    status_code=400,
+    message='{"message":"The model returned the following errors: The compiled grammar is too large, which would cause '
+    'performance issues. Simplify your tool schemas or reduce the number of strict tools."}',
+)
 _SCHEMA_REFUSAL: Final = BedrockError(
     status_code=400, message='{"message":"output_config.format.schema: pattern is too complex for structured output"}'
 )
@@ -58,8 +81,15 @@ _MODES: Final = pytest.mark.parametrize("asynchronous", [False, True], ids=["syn
 
 
 @_MODES
-def test_a_native_output_rejection_is_sent_again_once_with_the_fallback_params(asynchronous: bool) -> None:
-    bedrock: Final = ScriptedBedrock(errors=(_REJECTION, None), asynchronous=asynchronous)
+@pytest.mark.parametrize(
+    "rejection",
+    [_REJECTION, _GRAMMAR_REJECTION],
+    ids=["format_not_permitted", "compiled_grammar_too_large"],
+)
+def test_a_native_output_rejection_is_sent_again_once_with_the_fallback_params(
+    asynchronous: bool, rejection: BedrockError
+) -> None:
+    bedrock: Final = ScriptedBedrock(errors=(rejection, None), asynchronous=asynchronous)
 
     response: Final = _call(bedrock, _FALLBACK)
 
@@ -77,6 +107,19 @@ def test_a_second_native_output_rejection_reaches_the_caller(asynchronous: bool)
     assert len(bedrock.sent) == 2
 
 
+@_MODES
+def test_a_grammar_rejection_after_a_native_retry_reaches_the_caller_without_strict_tools_fallback(
+    asynchronous: bool,
+) -> None:
+    bedrock: Final = ScriptedBedrock(errors=(_GRAMMAR_REJECTION, _GRAMMAR_REJECTION), asynchronous=asynchronous)
+
+    with pytest.raises(BedrockError) as raised:
+        _resolve(call_with_native_output_fallback(bedrock, lambda: _FALLBACK, _MODEL))
+
+    assert raised.value is _GRAMMAR_REJECTION
+    assert bedrock.sent == (None, _FALLBACK)
+
+
 @_MODES
 @pytest.mark.parametrize(
     ("error", "fallback"),
@@ -155,13 +198,16 @@ _OTHER_400S_WITH_A_STRICT_TOOL: Final = tuple(
 
 
 def _call_with_strict_tools_fallback(
-    bedrock: ScriptedBedrock, fallback: NativeOutputFallback | None, strict_tools_fallback: NativeOutputFallback | None
+    bedrock: ScriptedBedrock,
+    fallback: NativeOutputFallback | None,
+    strict_tools_fallback: NativeOutputFallback | None,
+    model: str = _MODEL,
 ) -> object:
     return _resolve(
         call_with_native_output_fallback(
             bedrock,
             None if fallback is None else lambda: fallback,
-            _MODEL,
+            model,
             strict_tools_fallback=None if strict_tools_fallback is None else lambda: strict_tools_fallback,
         )
     )
@@ -223,3 +269,18 @@ def test_each_rejection_is_sent_again_with_its_own_fallback_when_both_are_set(
     _call_with_strict_tools_fallback(bedrock, _FALLBACK, _STRICT_FALLBACK)
 
     assert bedrock.sent == (None, retried_with)
+
+
+@_MODES
+def test_a_strict_tools_rejection_after_native_retry_composes_both_fallbacks(asynchronous: bool) -> None:
+    bedrock: Final = ScriptedBedrock(
+        errors=(_GRAMMAR_REJECTION, _GRAMMAR_REJECTION, None),
+        asynchronous=asynchronous,
+    )
+
+    response: Final = _call_with_strict_tools_fallback(
+        bedrock, _NATIVE_RETRY_WITH_STRICT_TOOLS, _STRICT_FALLBACK, "us.anthropic.claude-sonnet-4-6"
+    )
+
+    assert isinstance(response, ModelResponse) and response.id == "answer-3"
+    assert bedrock.sent == (None, _NATIVE_RETRY_WITH_STRICT_TOOLS, _COMPOSED_FALLBACK)
diff --git a/tests/unit/llms/bedrock/files/test_bedrock_files_transformation.py b/tests/unit/llms/bedrock/files/test_bedrock_files_transformation.py
index 512e1f325f4..a9edbd69ee3 100644
--- a/tests/unit/llms/bedrock/files/test_bedrock_files_transformation.py
+++ b/tests/unit/llms/bedrock/files/test_bedrock_files_transformation.py
@@ -2047,7 +2047,7 @@ class TestBedrockBatchAnthropicRowParams:
 
     @pytest.mark.parametrize(
         ("model", "native_output"),
-        [("bedrock/us.anthropic.claude-opus-4-8", False), (MODEL, True)],
+        [("bedrock/us.anthropic.claude-sonnet-5-5", False), (MODEL, True)],
         ids=["opt_in_native_output_model", "native_output_model"],
     )
     def test_thinking_json_schema_rows_use_native_output_only_on_models_that_always_take_it(
diff --git a/tests/unit/llms/bedrock/messages/invoke_transformations/test_anthropic_claude_transformation.py b/tests/unit/llms/bedrock/messages/invoke_transformations/test_anthropic_claude_transformation.py
index 07fabbf2393..ff4e3650464 100644
--- a/tests/unit/llms/bedrock/messages/invoke_transformations/test_anthropic_claude_transformation.py
+++ b/tests/unit/llms/bedrock/messages/invoke_transformations/test_anthropic_claude_transformation.py
@@ -4016,7 +4016,10 @@ _NATIVE_OUTPUT_REJECTION: Final = {
     "message": "The model returned the following errors: compilation exceeded limits: Schema is too complex."
 }
 _STALE_SIGNATURE_ERROR: Final = {"message": "messages.1.content.0: Invalid `signature` in `thinking` block"}
-_OPTED_OUT: Final = {"supports_bedrock_native_structured_output": False}
+_OPTED_OUT: Final = {
+    "supports_native_structured_output": False,
+    "supports_bedrock_native_structured_output": False,
+}
 _CONSTRAINED_SCHEMA: Final = {
     "type": "object",
     "properties": {
@@ -4158,21 +4161,21 @@ async def test_bedrock_messages_native_output_rejection_and_signature_400_each_g
 
 @pytest.mark.usefixtures("local_model_cost_map")
 @pytest.mark.parametrize(
-    ("model", "model_info", "error"),
+    ("model", "model_info", "error", "should_retry"),
     [
-        ("us.anthropic.claude-opus-4-8", None, {"message": "messages.0.content: Field required"}),
-        ("us.anthropic.claude-sonnet-4-6", None, _NATIVE_OUTPUT_REJECTION),
-        ("us.anthropic.claude-opus-4-8", _OPTED_OUT, _NATIVE_OUTPUT_REJECTION),
+        ("us.anthropic.claude-opus-4-8", None, {"message": "messages.0.content: Field required"}, False),
+        ("us.anthropic.claude-sonnet-4-6", None, _NATIVE_OUTPUT_REJECTION, True),
+        ("us.anthropic.claude-opus-4-8", _OPTED_OUT, _NATIVE_OUTPUT_REJECTION, False),
     ],
-    ids=["other_400", "native_model", "deployment_opt_out"],
+    ids=["other_400", "native_rejection", "deployment_opt_out"],
 )
-async def test_bedrock_messages_400_is_not_retried_unless_it_rejects_opt_in_native_output(
-    model: str, model_info: Mapping[str, object] | None, error: Mapping[str, object]
+async def test_bedrock_messages_retries_only_native_output_rejections(
+    model: str, model_info: Mapping[str, object] | None, error: Mapping[str, object], should_retry: bool
 ) -> None:
     bedrock, raised = await _send_bedrock_messages(model, model_info, [(400, error), (200, _ANTHROPIC_MESSAGE)])
 
-    assert isinstance(raised, litellm.BadRequestError)
-    assert len(bedrock.bodies) == 1
+    assert (raised is None) is should_retry
+    assert len(bedrock.bodies) == (2 if should_retry else 1)
 
 
 @pytest.mark.usefixtures("local_model_cost_map")
diff --git a/tests/unit/llms/bedrock/test_bedrock_common_utils.py b/tests/unit/llms/bedrock/test_bedrock_common_utils.py
index 80715105b7f..d8e9726358c 100644
--- a/tests/unit/llms/bedrock/test_bedrock_common_utils.py
+++ b/tests/unit/llms/bedrock/test_bedrock_common_utils.py
@@ -13,6 +13,7 @@ from litellm.llms.bedrock.common_utils import(
     bedrock_strict_tools_fallback,
     deployment_model_info,
     extract_model_name_from_bedrock_arn,
+    for_bedrock_json_tool_retry,
     get_bedrock_base_model,
     get_bedrock_cross_region_inference_regions,
     is_bedrock_native_output_rejection,
@@ -2328,6 +2329,10 @@ def test_bedrock_capability_model_reads_base_model_only_for_application_profile_
 
 _FORMAT_REJECTION: Final = "The model returned the following errors: output_config.format: Extra inputs are not permitted"
 _COMPILE_REJECTION: Final = "The model returned the following errors: compilation exceeded limits: Schema is too complex."
+_GRAMMAR_REJECTION: Final = (
+    "The model returned the following errors: The compiled grammar is too large, which would cause performance issues. "
+    "Simplify your tool schemas or reduce the number of strict tools."
+)
 _SCHEMA_PATTERN_REJECTION: Final = (
     "The model returned the following errors: output_config.format.schema: Unsupported regex feature in pattern "
     "field: pattern is too complex for structured output: reduce the {n,m} upper bound, narrow the character class "
@@ -2340,6 +2345,7 @@ _SCHEMA_PATTERN_REJECTION: Final = (
     [
         (400, f'{{"message":"{_FORMAT_REJECTION}"}}', True),
         (400, f'{{"message":"{_COMPILE_REJECTION}"}}', True),
+        (400, _GRAMMAR_REJECTION, True),
         (400, f'{{"message":"{_SCHEMA_PATTERN_REJECTION}"}}', True),
         (400, "Malformed input request: #: extraneous key [output_config] is not permitted", False),
         (400, "The model returned the following errors: messages.0.content: Field required", False),
@@ -2349,6 +2355,7 @@ _SCHEMA_PATTERN_REJECTION: Final = (
     ids=[
         "format_not_permitted",
         "schema_too_complex",
+        "compiled_grammar_too_large",
         "schema_pattern_too_complex",
         "other_key_not_permitted",
         "other_400",
@@ -2365,7 +2372,7 @@ def test_is_bedrock_native_output_rejection_matches_only_the_400s_that_reject_na
 @pytest.mark.parametrize(
     ("model", "model_info", "expected"),
     [
-        ("us.anthropic.claude-opus-4-8", None, True),
+        ("us.anthropic.claude-opus-4-8", None, False),
         ("global.anthropic.claude-sonnet-5", None, True),
         ("us-gov.anthropic.claude-opus-4-8", None, False),
         ("us.anthropic.claude-opus-4-8", {"supports_bedrock_native_structured_output": False}, False),
@@ -2389,9 +2396,43 @@ def test_without_bedrock_native_output_opt_in_turns_the_opt_in_off_and_keeps_the
         "us.anthropic.claude-opus-4-8", model_info=deployment_model_info(turned_off)
     )
     assert turned_off["api_base"] == "https://bedrock.example"
-    assert deployment_model_info(turned_off)["id"] == "deployment-1"
+    assert deployment_model_info(turned_off) == {
+        "id": "deployment-1",
+        "supports_bedrock_native_structured_output": False,
+    }
     assert litellm_params["model_info"] == {"id": "deployment-1"}
 
+    native_default: Final = without_bedrock_native_output_opt_in(
+        {"model_info": {"supports_native_structured_output": True}}
+    )
+    assert deployment_model_info(native_default) == {
+        "supports_native_structured_output": True,
+        "supports_bedrock_native_structured_output": False,
+    }
+
+
+def test_for_bedrock_json_tool_retry_disables_both_native_output_flags(local_model_cost_map: None) -> None:
+    litellm_params: Final = {
+        "model_info": {
+            "id": "deployment-1",
+            "supports_native_structured_output": True,
+            "supports_bedrock_native_structured_output": True,
+        }
+    }
+
+    retry_params: Final = for_bedrock_json_tool_retry(litellm_params)
+
+    assert deployment_model_info(retry_params) == {
+        "id": "deployment-1",
+        "supports_native_structured_output": False,
+        "supports_bedrock_native_structured_output": False,
+    }
+    assert litellm_params["model_info"] == {
+        "id": "deployment-1",
+        "supports_native_structured_output": True,
+        "supports_bedrock_native_structured_output": True,
+    }
+
 
 def test_bedrock_response_stream_shape_is_unavailable_when_botocore_describes_the_service_as_a_list():
     import litellm.llms.bedrock.common_utils as mod
diff --git a/tests/unit/test_utils_get_model_info.py b/tests/unit/test_utils_get_model_info.py
index 302a7d60cdd..d08742be4af 100644
--- a/tests/unit/test_utils_get_model_info.py
+++ b/tests/unit/test_utils_get_model_info.py
@@ -332,6 +332,18 @@ def _cross_region_profiles(
     )
 
 
+_BEDROCK_PROFILE_ONLY_NATIVE_OUTPUT_MODELS: Final = frozenset(
+    {
+        "anthropic.claude-opus-5-5",
+        "anthropic.claude-fable-5-1",
+        "anthropic.claude-sonnet-5",
+        "anthropic.claude-haiku-5-5",
+        "anthropic.claude-opus-5",
+        "anthropic.claude-opus-4-8",
+    }
+)
+
+
 def test_get_model_info_bedrock_cross_region_capability_parity():
     """
     Cross-region inference profiles carry litellm_provider "bedrock_converse", so the
@@ -362,6 +374,13 @@ def test_get_model_info_bedrock_cross_region_capability_parity():
             if _govcloud_may_lag(k, cap):
                 assert base_value or not v[cap], f"{cap} is on {k} but not on {base_model_key}"
                 continue
+            if (
+                cap == "supports_native_structured_output"
+                and base_model_key in _BEDROCK_PROFILE_ONLY_NATIVE_OUTPUT_MODELS
+                and v[cap] is True
+            ):
+                assert base_value is False, f"{cap} is already enabled on bare model {base_model_key}"
+                continue
             assert (
                 v[cap] == base_value
             ), f"{cap} is {v[cap]} on {k} but {base_value} on {base_model_key}"