diff --git a/.generator/schemas/v2/openapi.yaml b/.generator/schemas/v2/openapi.yaml
index 96018843d0..4b65adabc6 100644
--- a/.generator/schemas/v2/openapi.yaml
+++ b/.generator/schemas/v2/openapi.yaml
@@ -988,6 +988,14 @@ components:
       required: true
       schema:
         type: string
+    LLMObsAnnotationQueueInteractionIDPathParameter:
+      description: The ID of the interaction within the annotation queue.
+      example: "interaction-456"
+      in: path
+      name: interaction_id
+      required: true
+      schema:
+        type: string
     LLMObsDatasetIDPathParameter:
       description: The ID of the Agent Observability dataset.
       example: "9f64e5c7-dc5a-45c8-a17c-1b85f0bec97d"
@@ -56046,14 +56054,14 @@ components:
         annotations:
           description: List of annotations for this interaction.
           items:
-            $ref: "#/components/schemas/LLMObsAnnotationItem"
+            $ref: "#/components/schemas/LLMObsAnnotationItemResponse"
           type: array
         can_annotate:
           description: Whether the current caller can annotate this interaction.
           example: true
           type: boolean
         content_id:
-          description: Upstream entity identifier (trace ID, session ID, or deterministic display_block ID).
+          description: Upstream entity identifier (trace ID, session ID, or deterministic display_block or frontend ID).
           example: "trace-abc-123"
           type: string
         created_at:
@@ -56063,6 +56071,8 @@ components:
           type: string
         display_block:
           $ref: "#/components/schemas/LLMObsContentBlocks"
+        frontend:
+          $ref: "#/components/schemas/LLMObsFrontendContent"
         id:
           description: Unique identifier of the interaction.
           example: "interaction-456"
@@ -56093,11 +56103,44 @@ components:
         - can_annotate
         - annotations
       type: object
+    LLMObsAnnotatedInteractionDataAttributesResponse:
+      description: Attributes containing the annotated interaction.
+      properties:
+        annotated_interaction:
+          $ref: "#/components/schemas/LLMObsAnnotatedInteractionItem"
+      required:
+        - annotated_interaction
+      type: object
+    LLMObsAnnotatedInteractionDataResponse:
+      description: Data object for a single annotated interaction.
+      properties:
+        attributes:
+          $ref: "#/components/schemas/LLMObsAnnotatedInteractionDataAttributesResponse"
+        id:
+          description: The annotation queue ID.
+          example: "00000000-0000-0000-0000-000000000001"
+          type: string
+        type:
+          $ref: "#/components/schemas/LLMObsAnnotatedInteractionsType"
+      required:
+        - id
+        - type
+        - attributes
+      type: object
     LLMObsAnnotatedInteractionItem:
       description: An interaction with its associated annotations.
       oneOf:
         - $ref: "#/components/schemas/LLMObsTraceAnnotatedInteractionItem"
         - $ref: "#/components/schemas/LLMObsDisplayBlockAnnotatedInteractionItem"
+        - $ref: "#/components/schemas/LLMObsFrontendAnnotatedInteractionItem"
+    LLMObsAnnotatedInteractionResponse:
+      description: Response containing a single annotated interaction.
+      properties:
+        data:
+          $ref: "#/components/schemas/LLMObsAnnotatedInteractionDataResponse"
+      required:
+        - data
+      type: object
     LLMObsAnnotatedInteractionsByTraceDataAttributesResponse:
       description: Attributes of the cross-queue annotated interactions response.
       properties:
@@ -56236,51 +56279,6 @@ components:
       type: string
       x-enum-varnames:
         - PERMISSION_DENIED
-    LLMObsAnnotationItem:
-      description: A single annotation on an interaction.
-      properties:
-        created_at:
-          description: Timestamp when the annotation was created.
-          example: "2024-01-15T10:30:00Z"
-          format: date-time
-          type: string
-        created_by:
-          description: Identifier of the user who created the annotation.
-          example: "00000000-0000-0000-0000-000000000002"
-          type: string
-        id:
-          description: Unique identifier of the annotation.
-          example: "annotation-789"
-          type: string
-        interaction_id:
-          description: Identifier of the interaction this annotation belongs to.
-          example: "interaction-456"
-          type: string
-        label_values:
-          additionalProperties: {}
-          description: Label values for this annotation.
-          example:
-            - label_schema_id: "abc-123"
-              value: "good"
-          type: object
-        modified_at:
-          description: Timestamp when the annotation was last modified.
-          example: "2024-01-15T10:30:00Z"
-          format: date-time
-          type: string
-        modified_by:
-          description: Identifier of the user who last modified the annotation.
-          example: "00000000-0000-0000-0000-000000000002"
-          type: string
-      required:
-        - id
-        - interaction_id
-        - label_values
-        - created_by
-        - created_at
-        - modified_by
-        - modified_at
-      type: object
     LLMObsAnnotationItemResponse:
       description: A single annotation on an interaction, as returned by the API.
       properties:
@@ -56539,11 +56537,13 @@ components:
       oneOf:
         - $ref: "#/components/schemas/LLMObsTraceInteractionItem"
         - $ref: "#/components/schemas/LLMObsDisplayBlockInteractionItem"
+        - $ref: "#/components/schemas/LLMObsFrontendInteractionItem"
     LLMObsAnnotationQueueInteractionResponseItem:
       description: A single interaction result.
       oneOf:
         - $ref: "#/components/schemas/LLMObsTraceInteractionResponseItem"
         - $ref: "#/components/schemas/LLMObsDisplayBlockInteractionResponseItem"
+        - $ref: "#/components/schemas/LLMObsFrontendInteractionResponseItem"
     LLMObsAnnotationQueueInteractionsDataAttributesRequest:
       description: Attributes for adding interactions to an annotation queue.
       properties:
@@ -56915,6 +56915,7 @@ components:
         - experiment_trace
         - session
         - display_block
+        - frontend
       example: trace
       type: string
       x-enum-varnames:
@@ -56922,6 +56923,7 @@ components:
         - EXPERIMENT_TRACE
         - SESSION
         - DISPLAY_BLOCK
+        - FRONTEND
     LLMObsAzureOpenAIMetadata:
       description: Azure OpenAI-specific metadata for an integration account or inference request.
       properties:
@@ -58619,7 +58621,7 @@ components:
         annotations:
           description: List of annotations for this interaction.
           items:
-            $ref: "#/components/schemas/LLMObsAnnotationItem"
+            $ref: "#/components/schemas/LLMObsAnnotationItemResponse"
           type: array
         can_annotate:
           description: Whether the current caller can annotate this interaction.
@@ -59900,6 +59902,96 @@ components:
       required:
         - data
       type: object
+    LLMObsFrontendAnnotatedInteractionItem:
+      description: A frontend interaction with its associated annotations.
+      properties:
+        annotations:
+          description: List of annotations for this interaction.
+          items:
+            $ref: "#/components/schemas/LLMObsAnnotationItemResponse"
+          type: array
+        can_annotate:
+          description: Whether the current caller can annotate this interaction.
+          example: true
+          type: boolean
+        content_id:
+          description: Server-generated deterministic identifier derived from the content.
+          example: "9a87f3e2b1d4c5a6f8b3e2d1c4a7b5f6e3d2a1c4b7e5f8a3d6c2e1b4a7d5f8c2"
+          type: string
+        frontend:
+          $ref: "#/components/schemas/LLMObsFrontendContent"
+        id:
+          description: Unique identifier of the interaction.
+          example: "interaction-456"
+          type: string
+        type:
+          $ref: "#/components/schemas/LLMObsFrontendInteractionType"
+      required:
+        - id
+        - type
+        - content_id
+        - can_annotate
+        - annotations
+        - frontend
+      type: object
+    LLMObsFrontendContent:
+      description: Web content that makes up a `frontend` interaction.
+      properties:
+        code:
+          description: Caller-provided web content.
+          example: "<div>Hello world</div>"
+          type: string
+      required:
+        - code
+      type: object
+    LLMObsFrontendInteractionItem:
+      description: |-
+        An interaction whose rendered content is supplied directly as web
+        content. The server generates `content_id` deterministically from the
+        content.
+      properties:
+        frontend:
+          $ref: "#/components/schemas/LLMObsFrontendContent"
+        type:
+          $ref: "#/components/schemas/LLMObsFrontendInteractionType"
+      required:
+        - type
+        - frontend
+      type: object
+    LLMObsFrontendInteractionResponseItem:
+      description: A frontend interaction result.
+      properties:
+        already_existed:
+          description: Whether this interaction already existed in the queue.
+          example: false
+          type: boolean
+        content_id:
+          description: Server-generated deterministic identifier derived from the content.
+          example: "9a87f3e2b1d4c5a6f8b3e2d1c4a7b5f6e3d2a1c4b7e5f8a3d6c2e1b4a7d5f8c2"
+          type: string
+        frontend:
+          $ref: "#/components/schemas/LLMObsFrontendContent"
+        id:
+          description: Unique identifier of the interaction.
+          example: "00000000-0000-0000-0000-000000000000"
+          type: string
+        type:
+          $ref: "#/components/schemas/LLMObsFrontendInteractionType"
+      required:
+        - id
+        - type
+        - content_id
+        - already_existed
+        - frontend
+      type: object
+    LLMObsFrontendInteractionType:
+      description: Type discriminator for a `frontend` interaction.
+      enum:
+        - frontend
+      example: frontend
+      type: string
+      x-enum-varnames:
+        - FRONTEND
     LLMObsInferenceCode:
       description: A generated code snippet for running an inference request programmatically.
       properties:
@@ -62630,7 +62722,7 @@ components:
         annotations:
           description: List of annotations for this interaction.
           items:
-            $ref: "#/components/schemas/LLMObsAnnotationItem"
+            $ref: "#/components/schemas/LLMObsAnnotationItemResponse"
           type: array
         can_annotate:
           description: Whether the current caller can annotate this interaction.
@@ -166054,6 +166146,70 @@ paths:
       x-unstable: |-
         **Note**: This endpoint is in preview and is subject to change.
         If you have any feedback, contact [Datadog support](https://docs.datadoghq.com/help/).
+  /api/v2/llm-obs/v1/annotation-queues/{queue_id}/annotated-interactions/{interaction_id}:
+    get:
+      description: Retrieve a single interaction (trace, session, display block, or frontend content) and its annotations for a given annotation queue.
+      operationId: GetLLMObsAnnotatedInteraction
+      parameters:
+        - $ref: "#/components/parameters/LLMObsAnnotationQueueIDPathParameter"
+        - $ref: "#/components/parameters/LLMObsAnnotationQueueInteractionIDPathParameter"
+      responses:
+        "200":
+          content:
+            application/json:
+              examples:
+                default:
+                  value:
+                    data:
+                      attributes:
+                        annotated_interaction:
+                          annotations: []
+                          can_annotate: true
+                          content_id: trace-abc-123
+                          created_at: "2024-01-15T10:30:00Z"
+                          id: interaction-456
+                          modified_at: "2024-01-15T10:30:00Z"
+                          type: trace
+                      id: 00000000-0000-0000-0000-000000000001
+                      type: annotated_interactions
+              schema:
+                $ref: "#/components/schemas/LLMObsAnnotatedInteractionResponse"
+          description: OK
+        "400":
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/JSONAPIErrorResponse"
+          description: Bad Request
+        "401":
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/JSONAPIErrorResponse"
+          description: Unauthorized
+        "403":
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/JSONAPIErrorResponse"
+          description: Forbidden
+        "404":
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/JSONAPIErrorResponse"
+          description: Not Found
+        "429":
+          $ref: "#/components/responses/TooManyRequestsResponse"
+      security:
+        - apiKeyAuth: []
+          appKeyAuth: []
+      summary: Get an annotated queue interaction
+      tags:
+        - Agent Observability
+      x-unstable: |-
+        **Note**: This endpoint is in preview and is subject to change.
+        If you have any feedback, contact [Datadog support](https://docs.datadoghq.com/help/).
   /api/v2/llm-obs/v1/annotation-queues/{queue_id}/annotations:
     post:
       description: |-
@@ -166263,6 +166419,9 @@ paths:
         - `display_block`: omit `content_id` and provide the rendered content
           in `display_block`. The server generates `content_id` as a
           deterministic hash of the block list.
+        - `frontend`: omit `content_id` and provide the web content in
+          `frontend`. The server returns a deterministic `content_id` for the
+          content.
 
         Items of different types can be mixed in a single request.
       operationId: CreateLLMObsAnnotationQueueInteractions
@@ -166298,6 +166457,16 @@ paths:
                               type: json
                           type: display_block
                     type: interactions
+              frontend:
+                summary: Add a frontend interaction
+                value:
+                  data:
+                    attributes:
+                      interactions:
+                        - frontend:
+                            code: "<div>Hello world</div>"
+                          type: frontend
+                    type: interactions
             schema:
               $ref: "#/components/schemas/LLMObsAnnotationQueueInteractionsRequest"
         description: Add interactions payload.
@@ -166333,6 +166502,20 @@ paths:
                             type: display_block
                       id: 00000000-0000-0000-0000-000000000001
                       type: interactions
+                frontend:
+                  summary: frontend response
+                  value:
+                    data:
+                      attributes:
+                        interactions:
+                          - already_existed: false
+                            content_id: 9a87f3e2b1d4c5a6f8b3e2d1c4a7b5f6e3d2a1c4b7e5f8a3d6c2e1b4a7d5f8c2
+                            frontend:
+                              code: "<div>Hello world</div>"
+                            id: 00000000-0000-0000-0000-000000000000
+                            type: frontend
+                      id: 00000000-0000-0000-0000-000000000001
+                      type: interactions
               schema:
                 $ref: "#/components/schemas/LLMObsAnnotationQueueInteractionsResponse"
           description: Created
diff --git a/examples/v2/agent-observability/GetLLMObsAnnotatedInteraction.py b/examples/v2/agent-observability/GetLLMObsAnnotatedInteraction.py
new file mode 100644
index 0000000000..ff8cd09eb5
--- /dev/null
+++ b/examples/v2/agent-observability/GetLLMObsAnnotatedInteraction.py
@@ -0,0 +1,17 @@
+"""
+Get an annotated queue interaction returns "OK" response
+"""
+
+from datadog_api_client import ApiClient, Configuration
+from datadog_api_client.v2.api.agent_observability_api import AgentObservabilityApi
+
+configuration = Configuration()
+configuration.unstable_operations["get_llm_obs_annotated_interaction"] = True
+with ApiClient(configuration) as api_client:
+    api_instance = AgentObservabilityApi(api_client)
+    response = api_instance.get_llm_obs_annotated_interaction(
+        queue_id="queue_id",
+        interaction_id="interaction_id",
+    )
+
+    print(response)
diff --git a/src/datadog_api_client/configuration.py b/src/datadog_api_client/configuration.py
index 7c1e1cc136..fc665a8efd 100644
--- a/src/datadog_api_client/configuration.py
+++ b/src/datadog_api_client/configuration.py
@@ -286,6 +286,7 @@ def __init__(
                 "v2.delete_llm_obs_projects": False,
                 "v2.delete_llm_obs_prompt": False,
                 "v2.export_llm_obs_dataset": False,
+                "v2.get_llm_obs_annotated_interaction": False,
                 "v2.get_llm_obs_annotated_interactions": False,
                 "v2.get_llm_obs_annotated_interactions_by_trace_i_ds": False,
                 "v2.get_llm_obs_annotation_queue_label_schema": False,
diff --git a/src/datadog_api_client/v2/api/agent_observability_api.py b/src/datadog_api_client/v2/api/agent_observability_api.py
index 3cd16b79d1..a69983f550 100644
--- a/src/datadog_api_client/v2/api/agent_observability_api.py
+++ b/src/datadog_api_client/v2/api/agent_observability_api.py
@@ -24,6 +24,7 @@
 from datadog_api_client.v2.model.llm_obs_annotation_queue_request import LLMObsAnnotationQueueRequest
 from datadog_api_client.v2.model.llm_obs_annotation_queue_update_request import LLMObsAnnotationQueueUpdateRequest
 from datadog_api_client.v2.model.llm_obs_annotated_interactions_response import LLMObsAnnotatedInteractionsResponse
+from datadog_api_client.v2.model.llm_obs_annotated_interaction_response import LLMObsAnnotatedInteractionResponse
 from datadog_api_client.v2.model.llm_obs_annotations_response import LLMObsAnnotationsResponse
 from datadog_api_client.v2.model.llm_obs_annotations_request import LLMObsAnnotationsRequest
 from datadog_api_client.v2.model.llm_obs_delete_annotations_response import LLMObsDeleteAnnotationsResponse
@@ -741,6 +742,35 @@ def __init__(self, api_client=None):
             api_client=api_client,
         )
 
+        self._get_llm_obs_annotated_interaction_endpoint = _Endpoint(
+            settings={
+                "response_type": (LLMObsAnnotatedInteractionResponse,),
+                "auth": ["apiKeyAuth", "appKeyAuth"],
+                "endpoint_path": "/api/v2/llm-obs/v1/annotation-queues/{queue_id}/annotated-interactions/{interaction_id}",
+                "operation_id": "get_llm_obs_annotated_interaction",
+                "http_method": "GET",
+                "version": "v2",
+            },
+            params_map={
+                "queue_id": {
+                    "required": True,
+                    "openapi_types": (str,),
+                    "attribute": "queue_id",
+                    "location": "path",
+                },
+                "interaction_id": {
+                    "required": True,
+                    "openapi_types": (str,),
+                    "attribute": "interaction_id",
+                    "location": "path",
+                },
+            },
+            headers_map={
+                "accept": ["application/json"],
+            },
+            api_client=api_client,
+        )
+
         self._get_llm_obs_annotated_interactions_endpoint = _Endpoint(
             settings={
                 "response_type": (LLMObsAnnotatedInteractionsResponse,),
@@ -2277,6 +2307,9 @@ def create_llm_obs_annotation_queue_interactions(
         * ``display_block`` : omit ``content_id`` and provide the rendered content
           in ``display_block``. The server generates ``content_id`` as a
           deterministic hash of the block list.
+        * ``frontend`` : omit ``content_id`` and provide the web content in
+          ``frontend``. The server returns a deterministic ``content_id`` for the
+          content.
 
         Items of different types can be mixed in a single request.
 
@@ -2694,6 +2727,28 @@ def export_llm_obs_dataset(
 
         return self._export_llm_obs_dataset_endpoint.call_with_http_info(**kwargs)
 
+    def get_llm_obs_annotated_interaction(
+        self,
+        queue_id: str,
+        interaction_id: str,
+    ) -> LLMObsAnnotatedInteractionResponse:
+        """Get an annotated queue interaction.
+
+        Retrieve a single interaction (trace, session, display block, or frontend content) and its annotations for a given annotation queue.
+
+        :param queue_id: The ID of the Agent Observability annotation queue.
+        :type queue_id: str
+        :param interaction_id: The ID of the interaction within the annotation queue.
+        :type interaction_id: str
+        :rtype: LLMObsAnnotatedInteractionResponse
+        """
+        kwargs: Dict[str, Any] = {}
+        kwargs["queue_id"] = queue_id
+
+        kwargs["interaction_id"] = interaction_id
+
+        return self._get_llm_obs_annotated_interaction_endpoint.call_with_http_info(**kwargs)
+
     def get_llm_obs_annotated_interactions(
         self,
         queue_id: str,
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_by_trace_item.py b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_by_trace_item.py
index 56801353e9..101889095f 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_by_trace_item.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_by_trace_item.py
@@ -15,8 +15,9 @@
 
 
 if TYPE_CHECKING:
-    from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
+    from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
     from datadog_api_client.v2.model.llm_obs_content_block import LLMObsContentBlock
+    from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
     from datadog_api_client.v2.model.llm_obs_any_interaction_type import LLMObsAnyInteractionType
 
 
@@ -29,16 +30,18 @@ class LLMObsAnnotatedInteractionByTraceItem(ModelNormal):
 
     @cached_property
     def openapi_types(_):
-        from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
+        from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
         from datadog_api_client.v2.model.llm_obs_content_block import LLMObsContentBlock
+        from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
         from datadog_api_client.v2.model.llm_obs_any_interaction_type import LLMObsAnyInteractionType
 
         return {
-            "annotations": ([LLMObsAnnotationItem],),
+            "annotations": ([LLMObsAnnotationItemResponse],),
             "can_annotate": (bool,),
             "content_id": (str,),
             "created_at": (datetime,),
             "display_block": ([LLMObsContentBlock],),
+            "frontend": (LLMObsFrontendContent,),
             "id": (str,),
             "modified_at": (datetime,),
             "queue_id": (str,),
@@ -52,6 +55,7 @@ def openapi_types(_):
         "content_id": "content_id",
         "created_at": "created_at",
         "display_block": "display_block",
+        "frontend": "frontend",
         "id": "id",
         "modified_at": "modified_at",
         "queue_id": "queue_id",
@@ -61,7 +65,7 @@ def openapi_types(_):
 
     def __init__(
         self_,
-        annotations: List[LLMObsAnnotationItem],
+        annotations: List[LLMObsAnnotationItemResponse],
         can_annotate: bool,
         content_id: str,
         created_at: datetime,
@@ -71,18 +75,19 @@ def __init__(
         queue_name: str,
         type: LLMObsAnyInteractionType,
         display_block: Union[List[LLMObsContentBlock], UnsetType] = unset,
+        frontend: Union[LLMObsFrontendContent, UnsetType] = unset,
         **kwargs,
     ):
         """
         An annotated interaction returned by the cross-queue lookup, including the source queue metadata.
 
         :param annotations: List of annotations for this interaction.
-        :type annotations: [LLMObsAnnotationItem]
+        :type annotations: [LLMObsAnnotationItemResponse]
 
         :param can_annotate: Whether the current caller can annotate this interaction.
         :type can_annotate: bool
 
-        :param content_id: Upstream entity identifier (trace ID, session ID, or deterministic display_block ID).
+        :param content_id: Upstream entity identifier (trace ID, session ID, or deterministic display_block or frontend ID).
         :type content_id: str
 
         :param created_at: Timestamp when the interaction was added to the queue.
@@ -92,6 +97,9 @@ def __init__(
             Must contain at least one block.
         :type display_block: [LLMObsContentBlock], optional
 
+        :param frontend: Web content that makes up a ``frontend`` interaction.
+        :type frontend: LLMObsFrontendContent, optional
+
         :param id: Unique identifier of the interaction.
         :type id: str
 
@@ -109,6 +117,8 @@ def __init__(
         """
         if display_block is not unset:
             kwargs["display_block"] = display_block
+        if frontend is not unset:
+            kwargs["frontend"] = frontend
         super().__init__(kwargs)
 
         self_.annotations = annotations
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_data_attributes_response.py b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_data_attributes_response.py
new file mode 100644
index 0000000000..80bfdcf35d
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_data_attributes_response.py
@@ -0,0 +1,56 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+from typing import Union, TYPE_CHECKING
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+if TYPE_CHECKING:
+    from datadog_api_client.v2.model.llm_obs_annotated_interaction_item import LLMObsAnnotatedInteractionItem
+    from datadog_api_client.v2.model.llm_obs_trace_annotated_interaction_item import LLMObsTraceAnnotatedInteractionItem
+    from datadog_api_client.v2.model.llm_obs_display_block_annotated_interaction_item import (
+        LLMObsDisplayBlockAnnotatedInteractionItem,
+    )
+    from datadog_api_client.v2.model.llm_obs_frontend_annotated_interaction_item import (
+        LLMObsFrontendAnnotatedInteractionItem,
+    )
+
+
+class LLMObsAnnotatedInteractionDataAttributesResponse(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        from datadog_api_client.v2.model.llm_obs_annotated_interaction_item import LLMObsAnnotatedInteractionItem
+
+        return {
+            "annotated_interaction": (LLMObsAnnotatedInteractionItem,),
+        }
+
+    attribute_map = {
+        "annotated_interaction": "annotated_interaction",
+    }
+
+    def __init__(
+        self_,
+        annotated_interaction: Union[
+            LLMObsAnnotatedInteractionItem,
+            LLMObsTraceAnnotatedInteractionItem,
+            LLMObsDisplayBlockAnnotatedInteractionItem,
+            LLMObsFrontendAnnotatedInteractionItem,
+        ],
+        **kwargs,
+    ):
+        """
+        Attributes containing the annotated interaction.
+
+        :param annotated_interaction: An interaction with its associated annotations.
+        :type annotated_interaction: LLMObsAnnotatedInteractionItem
+        """
+        super().__init__(kwargs)
+
+        self_.annotated_interaction = annotated_interaction
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_data_response.py b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_data_response.py
new file mode 100644
index 0000000000..360c2f3987
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_data_response.py
@@ -0,0 +1,64 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+if TYPE_CHECKING:
+    from datadog_api_client.v2.model.llm_obs_annotated_interaction_data_attributes_response import (
+        LLMObsAnnotatedInteractionDataAttributesResponse,
+    )
+    from datadog_api_client.v2.model.llm_obs_annotated_interactions_type import LLMObsAnnotatedInteractionsType
+
+
+class LLMObsAnnotatedInteractionDataResponse(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        from datadog_api_client.v2.model.llm_obs_annotated_interaction_data_attributes_response import (
+            LLMObsAnnotatedInteractionDataAttributesResponse,
+        )
+        from datadog_api_client.v2.model.llm_obs_annotated_interactions_type import LLMObsAnnotatedInteractionsType
+
+        return {
+            "attributes": (LLMObsAnnotatedInteractionDataAttributesResponse,),
+            "id": (str,),
+            "type": (LLMObsAnnotatedInteractionsType,),
+        }
+
+    attribute_map = {
+        "attributes": "attributes",
+        "id": "id",
+        "type": "type",
+    }
+
+    def __init__(
+        self_,
+        attributes: LLMObsAnnotatedInteractionDataAttributesResponse,
+        id: str,
+        type: LLMObsAnnotatedInteractionsType,
+        **kwargs,
+    ):
+        """
+        Data object for a single annotated interaction.
+
+        :param attributes: Attributes containing the annotated interaction.
+        :type attributes: LLMObsAnnotatedInteractionDataAttributesResponse
+
+        :param id: The annotation queue ID.
+        :type id: str
+
+        :param type: Resource type for annotated interactions.
+        :type type: LLMObsAnnotatedInteractionsType
+        """
+        super().__init__(kwargs)
+
+        self_.attributes = attributes
+        self_.id = id
+        self_.type = type
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_item.py b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_item.py
index bbdf73ba35..32754e9310 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_item.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_item.py
@@ -16,7 +16,7 @@ def __init__(self, **kwargs):
         An interaction with its associated annotations.
 
         :param annotations: List of annotations for this interaction.
-        :type annotations: [LLMObsAnnotationItem]
+        :type annotations: [LLMObsAnnotationItemResponse]
 
         :param can_annotate: Whether the current caller can annotate this interaction.
         :type can_annotate: bool
@@ -39,6 +39,9 @@ def __init__(self, **kwargs):
         :param display_block: List of content blocks that make up a `display_block` interaction.
             Must contain at least one block.
         :type display_block: [LLMObsContentBlock]
+
+        :param frontend: Web content that makes up a `frontend` interaction.
+        :type frontend: LLMObsFrontendContent
         """
         super().__init__(kwargs)
 
@@ -57,10 +60,14 @@ def _composed_schemas(_):
         from datadog_api_client.v2.model.llm_obs_display_block_annotated_interaction_item import (
             LLMObsDisplayBlockAnnotatedInteractionItem,
         )
+        from datadog_api_client.v2.model.llm_obs_frontend_annotated_interaction_item import (
+            LLMObsFrontendAnnotatedInteractionItem,
+        )
 
         return {
             "oneOf": [
                 LLMObsTraceAnnotatedInteractionItem,
                 LLMObsDisplayBlockAnnotatedInteractionItem,
+                LLMObsFrontendAnnotatedInteractionItem,
             ],
         }
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_response.py b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_response.py
new file mode 100644
index 0000000000..59d1ccd9b3
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_annotated_interaction_response.py
@@ -0,0 +1,44 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+if TYPE_CHECKING:
+    from datadog_api_client.v2.model.llm_obs_annotated_interaction_data_response import (
+        LLMObsAnnotatedInteractionDataResponse,
+    )
+
+
+class LLMObsAnnotatedInteractionResponse(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        from datadog_api_client.v2.model.llm_obs_annotated_interaction_data_response import (
+            LLMObsAnnotatedInteractionDataResponse,
+        )
+
+        return {
+            "data": (LLMObsAnnotatedInteractionDataResponse,),
+        }
+
+    attribute_map = {
+        "data": "data",
+    }
+
+    def __init__(self_, data: LLMObsAnnotatedInteractionDataResponse, **kwargs):
+        """
+        Response containing a single annotated interaction.
+
+        :param data: Data object for a single annotated interaction.
+        :type data: LLMObsAnnotatedInteractionDataResponse
+        """
+        super().__init__(kwargs)
+
+        self_.data = data
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotated_interactions_data_attributes_response.py b/src/datadog_api_client/v2/model/llm_obs_annotated_interactions_data_attributes_response.py
index 5718c2519e..070797030a 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotated_interactions_data_attributes_response.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotated_interactions_data_attributes_response.py
@@ -17,6 +17,9 @@
     from datadog_api_client.v2.model.llm_obs_display_block_annotated_interaction_item import (
         LLMObsDisplayBlockAnnotatedInteractionItem,
     )
+    from datadog_api_client.v2.model.llm_obs_frontend_annotated_interaction_item import (
+        LLMObsFrontendAnnotatedInteractionItem,
+    )
 
 
 class LLMObsAnnotatedInteractionsDataAttributesResponse(ModelNormal):
@@ -39,6 +42,7 @@ def __init__(
                 LLMObsAnnotatedInteractionItem,
                 LLMObsTraceAnnotatedInteractionItem,
                 LLMObsDisplayBlockAnnotatedInteractionItem,
+                LLMObsFrontendAnnotatedInteractionItem,
             ]
         ],
         **kwargs,
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotation_item.py b/src/datadog_api_client/v2/model/llm_obs_annotation_item.py
deleted file mode 100644
index dd9408f296..0000000000
--- a/src/datadog_api_client/v2/model/llm_obs_annotation_item.py
+++ /dev/null
@@ -1,99 +0,0 @@
-# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
-# This product includes software developed at Datadog (https://www.datadoghq.com/).
-# Copyright 2019-Present Datadog, Inc.
-from __future__ import annotations
-
-from typing import Any, Dict
-
-from datadog_api_client.model_utils import (
-    ModelNormal,
-    cached_property,
-    date,
-    datetime,
-    none_type,
-    UUID,
-)
-
-
-class LLMObsAnnotationItem(ModelNormal):
-    @cached_property
-    def openapi_types(_):
-        return {
-            "created_at": (datetime,),
-            "created_by": (str,),
-            "id": (str,),
-            "interaction_id": (str,),
-            "label_values": (
-                {
-                    str: (
-                        bool,
-                        date,
-                        datetime,
-                        dict,
-                        float,
-                        int,
-                        list,
-                        str,
-                        UUID,
-                        none_type,
-                    )
-                },
-            ),
-            "modified_at": (datetime,),
-            "modified_by": (str,),
-        }
-
-    attribute_map = {
-        "created_at": "created_at",
-        "created_by": "created_by",
-        "id": "id",
-        "interaction_id": "interaction_id",
-        "label_values": "label_values",
-        "modified_at": "modified_at",
-        "modified_by": "modified_by",
-    }
-
-    def __init__(
-        self_,
-        created_at: datetime,
-        created_by: str,
-        id: str,
-        interaction_id: str,
-        label_values: Dict[str, Any],
-        modified_at: datetime,
-        modified_by: str,
-        **kwargs,
-    ):
-        """
-        A single annotation on an interaction.
-
-        :param created_at: Timestamp when the annotation was created.
-        :type created_at: datetime
-
-        :param created_by: Identifier of the user who created the annotation.
-        :type created_by: str
-
-        :param id: Unique identifier of the annotation.
-        :type id: str
-
-        :param interaction_id: Identifier of the interaction this annotation belongs to.
-        :type interaction_id: str
-
-        :param label_values: Label values for this annotation.
-        :type label_values: {str: (bool, date, datetime, dict, float, int, list, str, UUID, none_type,)}
-
-        :param modified_at: Timestamp when the annotation was last modified.
-        :type modified_at: datetime
-
-        :param modified_by: Identifier of the user who last modified the annotation.
-        :type modified_by: str
-        """
-        super().__init__(kwargs)
-
-        self_.created_at = created_at
-        self_.created_by = created_by
-        self_.id = id
-        self_.interaction_id = interaction_id
-        self_.label_values = label_values
-        self_.modified_at = modified_at
-        self_.modified_by = modified_by
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_item.py b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_item.py
index 7ef54bf709..94948b8a23 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_item.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_item.py
@@ -24,6 +24,9 @@ def __init__(self, **kwargs):
         :param display_block: List of content blocks that make up a `display_block` interaction.
             Must contain at least one block.
         :type display_block: [LLMObsContentBlock]
+
+        :param frontend: Web content that makes up a `frontend` interaction.
+        :type frontend: LLMObsFrontendContent
         """
         super().__init__(kwargs)
 
@@ -38,10 +41,12 @@ def _composed_schemas(_):
         # loading
         from datadog_api_client.v2.model.llm_obs_trace_interaction_item import LLMObsTraceInteractionItem
         from datadog_api_client.v2.model.llm_obs_display_block_interaction_item import LLMObsDisplayBlockInteractionItem
+        from datadog_api_client.v2.model.llm_obs_frontend_interaction_item import LLMObsFrontendInteractionItem
 
         return {
             "oneOf": [
                 LLMObsTraceInteractionItem,
                 LLMObsDisplayBlockInteractionItem,
+                LLMObsFrontendInteractionItem,
             ],
         }
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_response_item.py b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_response_item.py
index ce5d246f31..7a4068fb38 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_response_item.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interaction_response_item.py
@@ -36,6 +36,9 @@ def __init__(self, **kwargs):
         :param display_block: List of content blocks that make up a `display_block` interaction.
             Must contain at least one block.
         :type display_block: [LLMObsContentBlock]
+
+        :param frontend: Web content that makes up a `frontend` interaction.
+        :type frontend: LLMObsFrontendContent
         """
         super().__init__(kwargs)
 
@@ -54,10 +57,14 @@ def _composed_schemas(_):
         from datadog_api_client.v2.model.llm_obs_display_block_interaction_response_item import (
             LLMObsDisplayBlockInteractionResponseItem,
         )
+        from datadog_api_client.v2.model.llm_obs_frontend_interaction_response_item import (
+            LLMObsFrontendInteractionResponseItem,
+        )
 
         return {
             "oneOf": [
                 LLMObsTraceInteractionResponseItem,
                 LLMObsDisplayBlockInteractionResponseItem,
+                LLMObsFrontendInteractionResponseItem,
             ],
         }
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_request.py b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_request.py
index 49c7b1be91..295ab6fcb3 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_request.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_request.py
@@ -17,6 +17,7 @@
     )
     from datadog_api_client.v2.model.llm_obs_trace_interaction_item import LLMObsTraceInteractionItem
     from datadog_api_client.v2.model.llm_obs_display_block_interaction_item import LLMObsDisplayBlockInteractionItem
+    from datadog_api_client.v2.model.llm_obs_frontend_interaction_item import LLMObsFrontendInteractionItem
 
 
 class LLMObsAnnotationQueueInteractionsDataAttributesRequest(ModelNormal):
@@ -43,7 +44,12 @@ def openapi_types(_):
     def __init__(
         self_,
         interactions: List[
-            Union[LLMObsAnnotationQueueInteractionItem, LLMObsTraceInteractionItem, LLMObsDisplayBlockInteractionItem]
+            Union[
+                LLMObsAnnotationQueueInteractionItem,
+                LLMObsTraceInteractionItem,
+                LLMObsDisplayBlockInteractionItem,
+                LLMObsFrontendInteractionItem,
+            ]
         ],
         **kwargs,
     ):
diff --git a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_response.py b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_response.py
index 97d7713cca..d336768636 100644
--- a/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_response.py
+++ b/src/datadog_api_client/v2/model/llm_obs_annotation_queue_interactions_data_attributes_response.py
@@ -19,6 +19,9 @@
     from datadog_api_client.v2.model.llm_obs_display_block_interaction_response_item import (
         LLMObsDisplayBlockInteractionResponseItem,
     )
+    from datadog_api_client.v2.model.llm_obs_frontend_interaction_response_item import (
+        LLMObsFrontendInteractionResponseItem,
+    )
 
 
 class LLMObsAnnotationQueueInteractionsDataAttributesResponse(ModelNormal):
@@ -43,6 +46,7 @@ def __init__(
                 LLMObsAnnotationQueueInteractionResponseItem,
                 LLMObsTraceInteractionResponseItem,
                 LLMObsDisplayBlockInteractionResponseItem,
+                LLMObsFrontendInteractionResponseItem,
             ]
         ],
         **kwargs,
diff --git a/src/datadog_api_client/v2/model/llm_obs_any_interaction_type.py b/src/datadog_api_client/v2/model/llm_obs_any_interaction_type.py
index 12f010a070..5b5ac2aaff 100644
--- a/src/datadog_api_client/v2/model/llm_obs_any_interaction_type.py
+++ b/src/datadog_api_client/v2/model/llm_obs_any_interaction_type.py
@@ -16,7 +16,7 @@ class LLMObsAnyInteractionType(ModelSimple):
     """
     Type of an annotated interaction.
 
-    :param value: Must be one of ["trace", "experiment_trace", "session", "display_block"].
+    :param value: Must be one of ["trace", "experiment_trace", "session", "display_block", "frontend"].
     :type value: str
     """
 
@@ -25,11 +25,13 @@ class LLMObsAnyInteractionType(ModelSimple):
         "experiment_trace",
         "session",
         "display_block",
+        "frontend",
     }
     TRACE: ClassVar["LLMObsAnyInteractionType"]
     EXPERIMENT_TRACE: ClassVar["LLMObsAnyInteractionType"]
     SESSION: ClassVar["LLMObsAnyInteractionType"]
     DISPLAY_BLOCK: ClassVar["LLMObsAnyInteractionType"]
+    FRONTEND: ClassVar["LLMObsAnyInteractionType"]
 
     @cached_property
     def openapi_types(_):
@@ -42,3 +44,4 @@ def openapi_types(_):
 LLMObsAnyInteractionType.EXPERIMENT_TRACE = LLMObsAnyInteractionType("experiment_trace")
 LLMObsAnyInteractionType.SESSION = LLMObsAnyInteractionType("session")
 LLMObsAnyInteractionType.DISPLAY_BLOCK = LLMObsAnyInteractionType("display_block")
+LLMObsAnyInteractionType.FRONTEND = LLMObsAnyInteractionType("frontend")
diff --git a/src/datadog_api_client/v2/model/llm_obs_display_block_annotated_interaction_item.py b/src/datadog_api_client/v2/model/llm_obs_display_block_annotated_interaction_item.py
index 0eb8a65c98..e09e98661e 100644
--- a/src/datadog_api_client/v2/model/llm_obs_display_block_annotated_interaction_item.py
+++ b/src/datadog_api_client/v2/model/llm_obs_display_block_annotated_interaction_item.py
@@ -12,7 +12,7 @@
 
 
 if TYPE_CHECKING:
-    from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
+    from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
     from datadog_api_client.v2.model.llm_obs_content_block import LLMObsContentBlock
     from datadog_api_client.v2.model.llm_obs_display_block_interaction_type import LLMObsDisplayBlockInteractionType
 
@@ -26,12 +26,12 @@ class LLMObsDisplayBlockAnnotatedInteractionItem(ModelNormal):
 
     @cached_property
     def openapi_types(_):
-        from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
+        from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
         from datadog_api_client.v2.model.llm_obs_content_block import LLMObsContentBlock
         from datadog_api_client.v2.model.llm_obs_display_block_interaction_type import LLMObsDisplayBlockInteractionType
 
         return {
-            "annotations": ([LLMObsAnnotationItem],),
+            "annotations": ([LLMObsAnnotationItemResponse],),
             "can_annotate": (bool,),
             "content_id": (str,),
             "display_block": ([LLMObsContentBlock],),
@@ -50,7 +50,7 @@ def openapi_types(_):
 
     def __init__(
         self_,
-        annotations: List[LLMObsAnnotationItem],
+        annotations: List[LLMObsAnnotationItemResponse],
         can_annotate: bool,
         content_id: str,
         display_block: List[LLMObsContentBlock],
@@ -62,7 +62,7 @@ def __init__(
         A display_block interaction with its associated annotations.
 
         :param annotations: List of annotations for this interaction.
-        :type annotations: [LLMObsAnnotationItem]
+        :type annotations: [LLMObsAnnotationItemResponse]
 
         :param can_annotate: Whether the current caller can annotate this interaction.
         :type can_annotate: bool
diff --git a/src/datadog_api_client/v2/model/llm_obs_frontend_annotated_interaction_item.py b/src/datadog_api_client/v2/model/llm_obs_frontend_annotated_interaction_item.py
new file mode 100644
index 0000000000..0809a66eca
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_frontend_annotated_interaction_item.py
@@ -0,0 +1,83 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+from typing import List, TYPE_CHECKING
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+if TYPE_CHECKING:
+    from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
+    from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+    from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
+
+
+class LLMObsFrontendAnnotatedInteractionItem(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
+        from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+        from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
+
+        return {
+            "annotations": ([LLMObsAnnotationItemResponse],),
+            "can_annotate": (bool,),
+            "content_id": (str,),
+            "frontend": (LLMObsFrontendContent,),
+            "id": (str,),
+            "type": (LLMObsFrontendInteractionType,),
+        }
+
+    attribute_map = {
+        "annotations": "annotations",
+        "can_annotate": "can_annotate",
+        "content_id": "content_id",
+        "frontend": "frontend",
+        "id": "id",
+        "type": "type",
+    }
+
+    def __init__(
+        self_,
+        annotations: List[LLMObsAnnotationItemResponse],
+        can_annotate: bool,
+        content_id: str,
+        frontend: LLMObsFrontendContent,
+        id: str,
+        type: LLMObsFrontendInteractionType,
+        **kwargs,
+    ):
+        """
+        A frontend interaction with its associated annotations.
+
+        :param annotations: List of annotations for this interaction.
+        :type annotations: [LLMObsAnnotationItemResponse]
+
+        :param can_annotate: Whether the current caller can annotate this interaction.
+        :type can_annotate: bool
+
+        :param content_id: Server-generated deterministic identifier derived from the content.
+        :type content_id: str
+
+        :param frontend: Web content that makes up a ``frontend`` interaction.
+        :type frontend: LLMObsFrontendContent
+
+        :param id: Unique identifier of the interaction.
+        :type id: str
+
+        :param type: Type discriminator for a ``frontend`` interaction.
+        :type type: LLMObsFrontendInteractionType
+        """
+        super().__init__(kwargs)
+
+        self_.annotations = annotations
+        self_.can_annotate = can_annotate
+        self_.content_id = content_id
+        self_.frontend = frontend
+        self_.id = id
+        self_.type = type
diff --git a/src/datadog_api_client/v2/model/llm_obs_frontend_content.py b/src/datadog_api_client/v2/model/llm_obs_frontend_content.py
new file mode 100644
index 0000000000..bb1c5001c2
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_frontend_content.py
@@ -0,0 +1,33 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+class LLMObsFrontendContent(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        return {
+            "code": (str,),
+        }
+
+    attribute_map = {
+        "code": "code",
+    }
+
+    def __init__(self_, code: str, **kwargs):
+        """
+        Web content that makes up a ``frontend`` interaction.
+
+        :param code: Caller-provided web content.
+        :type code: str
+        """
+        super().__init__(kwargs)
+
+        self_.code = code
diff --git a/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_item.py b/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_item.py
new file mode 100644
index 0000000000..2261eac84d
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_item.py
@@ -0,0 +1,50 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+if TYPE_CHECKING:
+    from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+    from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
+
+
+class LLMObsFrontendInteractionItem(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+        from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
+
+        return {
+            "frontend": (LLMObsFrontendContent,),
+            "type": (LLMObsFrontendInteractionType,),
+        }
+
+    attribute_map = {
+        "frontend": "frontend",
+        "type": "type",
+    }
+
+    def __init__(self_, frontend: LLMObsFrontendContent, type: LLMObsFrontendInteractionType, **kwargs):
+        """
+        An interaction whose rendered content is supplied directly as web
+        content. The server generates ``content_id`` deterministically from the
+        content.
+
+        :param frontend: Web content that makes up a ``frontend`` interaction.
+        :type frontend: LLMObsFrontendContent
+
+        :param type: Type discriminator for a ``frontend`` interaction.
+        :type type: LLMObsFrontendInteractionType
+        """
+        super().__init__(kwargs)
+
+        self_.frontend = frontend
+        self_.type = type
diff --git a/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_response_item.py b/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_response_item.py
new file mode 100644
index 0000000000..82544f7cff
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_response_item.py
@@ -0,0 +1,74 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
+from datadog_api_client.model_utils import (
+    ModelNormal,
+    cached_property,
+)
+
+
+if TYPE_CHECKING:
+    from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+    from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
+
+
+class LLMObsFrontendInteractionResponseItem(ModelNormal):
+    @cached_property
+    def openapi_types(_):
+        from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+        from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
+
+        return {
+            "already_existed": (bool,),
+            "content_id": (str,),
+            "frontend": (LLMObsFrontendContent,),
+            "id": (str,),
+            "type": (LLMObsFrontendInteractionType,),
+        }
+
+    attribute_map = {
+        "already_existed": "already_existed",
+        "content_id": "content_id",
+        "frontend": "frontend",
+        "id": "id",
+        "type": "type",
+    }
+
+    def __init__(
+        self_,
+        already_existed: bool,
+        content_id: str,
+        frontend: LLMObsFrontendContent,
+        id: str,
+        type: LLMObsFrontendInteractionType,
+        **kwargs,
+    ):
+        """
+        A frontend interaction result.
+
+        :param already_existed: Whether this interaction already existed in the queue.
+        :type already_existed: bool
+
+        :param content_id: Server-generated deterministic identifier derived from the content.
+        :type content_id: str
+
+        :param frontend: Web content that makes up a ``frontend`` interaction.
+        :type frontend: LLMObsFrontendContent
+
+        :param id: Unique identifier of the interaction.
+        :type id: str
+
+        :param type: Type discriminator for a ``frontend`` interaction.
+        :type type: LLMObsFrontendInteractionType
+        """
+        super().__init__(kwargs)
+
+        self_.already_existed = already_existed
+        self_.content_id = content_id
+        self_.frontend = frontend
+        self_.id = id
+        self_.type = type
diff --git a/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_type.py b/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_type.py
new file mode 100644
index 0000000000..58be50f68c
--- /dev/null
+++ b/src/datadog_api_client/v2/model/llm_obs_frontend_interaction_type.py
@@ -0,0 +1,35 @@
+# Unless explicitly stated otherwise all files in this repository are licensed under the Apache-2.0 License.
+# This product includes software developed at Datadog (https://www.datadoghq.com/).
+# Copyright 2019-Present Datadog, Inc.
+from __future__ import annotations
+
+
+from datadog_api_client.model_utils import (
+    ModelSimple,
+    cached_property,
+)
+
+from typing import ClassVar
+
+
+class LLMObsFrontendInteractionType(ModelSimple):
+    """
+    Type discriminator for a `frontend` interaction.
+
+    :param value: If omitted defaults to "frontend". Must be one of ["frontend"].
+    :type value: str
+    """
+
+    allowed_values = {
+        "frontend",
+    }
+    FRONTEND: ClassVar["LLMObsFrontendInteractionType"]
+
+    @cached_property
+    def openapi_types(_):
+        return {
+            "value": (str,),
+        }
+
+
+LLMObsFrontendInteractionType.FRONTEND = LLMObsFrontendInteractionType("frontend")
diff --git a/src/datadog_api_client/v2/model/llm_obs_trace_annotated_interaction_item.py b/src/datadog_api_client/v2/model/llm_obs_trace_annotated_interaction_item.py
index da96e519af..65b0642e0c 100644
--- a/src/datadog_api_client/v2/model/llm_obs_trace_annotated_interaction_item.py
+++ b/src/datadog_api_client/v2/model/llm_obs_trace_annotated_interaction_item.py
@@ -13,18 +13,18 @@
 
 
 if TYPE_CHECKING:
-    from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
+    from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
     from datadog_api_client.v2.model.llm_obs_trace_interaction_type import LLMObsTraceInteractionType
 
 
 class LLMObsTraceAnnotatedInteractionItem(ModelNormal):
     @cached_property
     def openapi_types(_):
-        from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
+        from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
         from datadog_api_client.v2.model.llm_obs_trace_interaction_type import LLMObsTraceInteractionType
 
         return {
-            "annotations": ([LLMObsAnnotationItem],),
+            "annotations": ([LLMObsAnnotationItemResponse],),
             "can_annotate": (bool,),
             "content_id": (str,),
             "created_at": (datetime,),
@@ -45,7 +45,7 @@ def openapi_types(_):
 
     def __init__(
         self_,
-        annotations: List[LLMObsAnnotationItem],
+        annotations: List[LLMObsAnnotationItemResponse],
         can_annotate: bool,
         content_id: str,
         created_at: datetime,
@@ -58,7 +58,7 @@ def __init__(
         A trace, experiment trace, or session interaction with its associated annotations.
 
         :param annotations: List of annotations for this interaction.
-        :type annotations: [LLMObsAnnotationItem]
+        :type annotations: [LLMObsAnnotationItemResponse]
 
         :param can_annotate: Whether the current caller can annotate this interaction.
         :type can_annotate: bool
diff --git a/src/datadog_api_client/v2/models/__init__.py b/src/datadog_api_client/v2/models/__init__.py
index ba4fdd992c..35137998a3 100644
--- a/src/datadog_api_client/v2/models/__init__.py
+++ b/src/datadog_api_client/v2/models/__init__.py
@@ -4458,7 +4458,14 @@
 from datadog_api_client.v2.model.llm_obs_annotated_interaction_by_trace_item import (
     LLMObsAnnotatedInteractionByTraceItem,
 )
+from datadog_api_client.v2.model.llm_obs_annotated_interaction_data_attributes_response import (
+    LLMObsAnnotatedInteractionDataAttributesResponse,
+)
+from datadog_api_client.v2.model.llm_obs_annotated_interaction_data_response import (
+    LLMObsAnnotatedInteractionDataResponse,
+)
 from datadog_api_client.v2.model.llm_obs_annotated_interaction_item import LLMObsAnnotatedInteractionItem
+from datadog_api_client.v2.model.llm_obs_annotated_interaction_response import LLMObsAnnotatedInteractionResponse
 from datadog_api_client.v2.model.llm_obs_annotated_interactions_by_trace_data_attributes_response import (
     LLMObsAnnotatedInteractionsByTraceDataAttributesResponse,
 )
@@ -4482,7 +4489,6 @@
 from datadog_api_client.v2.model.llm_obs_annotation_assessment import LLMObsAnnotationAssessment
 from datadog_api_client.v2.model.llm_obs_annotation_error import LLMObsAnnotationError
 from datadog_api_client.v2.model.llm_obs_annotation_error_code import LLMObsAnnotationErrorCode
-from datadog_api_client.v2.model.llm_obs_annotation_item import LLMObsAnnotationItem
 from datadog_api_client.v2.model.llm_obs_annotation_item_response import LLMObsAnnotationItemResponse
 from datadog_api_client.v2.model.llm_obs_annotation_label_value import LLMObsAnnotationLabelValue
 from datadog_api_client.v2.model.llm_obs_annotation_label_value_response import LLMObsAnnotationLabelValueResponse
@@ -4844,6 +4850,13 @@
 )
 from datadog_api_client.v2.model.llm_obs_experimentation_type import LLMObsExperimentationType
 from datadog_api_client.v2.model.llm_obs_experiments_response import LLMObsExperimentsResponse
+from datadog_api_client.v2.model.llm_obs_frontend_annotated_interaction_item import (
+    LLMObsFrontendAnnotatedInteractionItem,
+)
+from datadog_api_client.v2.model.llm_obs_frontend_content import LLMObsFrontendContent
+from datadog_api_client.v2.model.llm_obs_frontend_interaction_item import LLMObsFrontendInteractionItem
+from datadog_api_client.v2.model.llm_obs_frontend_interaction_response_item import LLMObsFrontendInteractionResponseItem
+from datadog_api_client.v2.model.llm_obs_frontend_interaction_type import LLMObsFrontendInteractionType
 from datadog_api_client.v2.model.llm_obs_inference_code import LLMObsInferenceCode
 from datadog_api_client.v2.model.llm_obs_inference_content import LLMObsInferenceContent
 from datadog_api_client.v2.model.llm_obs_inference_content_value import LLMObsInferenceContentValue
@@ -14608,7 +14621,10 @@
     "KindObj",
     "KindResponseMeta",
     "LLMObsAnnotatedInteractionByTraceItem",
+    "LLMObsAnnotatedInteractionDataAttributesResponse",
+    "LLMObsAnnotatedInteractionDataResponse",
     "LLMObsAnnotatedInteractionItem",
+    "LLMObsAnnotatedInteractionResponse",
     "LLMObsAnnotatedInteractionsByTraceDataAttributesResponse",
     "LLMObsAnnotatedInteractionsByTraceDataResponse",
     "LLMObsAnnotatedInteractionsByTraceResponse",
@@ -14620,7 +14636,6 @@
     "LLMObsAnnotationAssessment",
     "LLMObsAnnotationError",
     "LLMObsAnnotationErrorCode",
-    "LLMObsAnnotationItem",
     "LLMObsAnnotationItemResponse",
     "LLMObsAnnotationLabelValue",
     "LLMObsAnnotationLabelValueResponse",
@@ -14844,6 +14859,11 @@
     "LLMObsExperimentationSortFieldDirection",
     "LLMObsExperimentationType",
     "LLMObsExperimentsResponse",
+    "LLMObsFrontendAnnotatedInteractionItem",
+    "LLMObsFrontendContent",
+    "LLMObsFrontendInteractionItem",
+    "LLMObsFrontendInteractionResponseItem",
+    "LLMObsFrontendInteractionType",
     "LLMObsInferenceCode",
     "LLMObsInferenceContent",
     "LLMObsInferenceContentValue",
diff --git a/tests/generated-test/test-server b/tests/generated-test/test-server
index 899230cbcc..a7224b2c64 100755
--- a/tests/generated-test/test-server
+++ b/tests/generated-test/test-server
@@ -16,7 +16,7 @@ import re
 import tempfile
 import threading
 import uuid
-from datetime import datetime, timezone
+from datetime import UTC, datetime
 from http import HTTPStatus
 from http.server import BaseHTTPRequestHandler, ThreadingHTTPServer
 from pathlib import Path
@@ -435,7 +435,8 @@ def _json_contains(actual: Any, expected: Any) -> bool:
         return all(key in actual and _json_contains(actual[key], value) for key, value in expected.items())
     if isinstance(expected, list) and isinstance(actual, list):
         return len(expected) == len(actual) and all(
-            _json_contains(actual_item, expected_item) for actual_item, expected_item in zip(actual, expected)
+            _json_contains(actual_item, expected_item)
+            for actual_item, expected_item in zip(actual, expected, strict=False)
         )
     return actual == expected
 
@@ -460,7 +461,7 @@ def _slug(value: str) -> str:
 
 
 def _now_iso() -> str:
-    return datetime.now(timezone.utc).isoformat().replace("+00:00", "Z")
+    return datetime.now(UTC).isoformat().replace("+00:00", "Z")
 
 
 def _read_json(path: Path) -> dict[str, Any]:
diff --git a/tests/v2/features/agent_observability.feature b/tests/v2/features/agent_observability.feature
index acf08cf0dd..3136a1312f 100644
--- a/tests/v2/features/agent_observability.feature
+++ b/tests/v2/features/agent_observability.feature
@@ -782,6 +782,33 @@ Feature: Agent Observability
     When the request is sent
     Then the response status is 200 OK
 
+  @generated @skip @team:DataDog/ml-observability
+  Scenario: Get an annotated queue interaction returns "Bad Request" response
+    Given operation "GetLLMObsAnnotatedInteraction" enabled
+    And new "GetLLMObsAnnotatedInteraction" request
+    And request contains "queue_id" parameter from "REPLACE.ME"
+    And request contains "interaction_id" parameter from "REPLACE.ME"
+    When the request is sent
+    Then the response status is 400 Bad Request
+
+  @generated @skip @team:DataDog/ml-observability
+  Scenario: Get an annotated queue interaction returns "Not Found" response
+    Given operation "GetLLMObsAnnotatedInteraction" enabled
+    And new "GetLLMObsAnnotatedInteraction" request
+    And request contains "queue_id" parameter from "REPLACE.ME"
+    And request contains "interaction_id" parameter from "REPLACE.ME"
+    When the request is sent
+    Then the response status is 404 Not Found
+
+  @generated @skip @team:DataDog/ml-observability
+  Scenario: Get an annotated queue interaction returns "OK" response
+    Given operation "GetLLMObsAnnotatedInteraction" enabled
+    And new "GetLLMObsAnnotatedInteraction" request
+    And request contains "queue_id" parameter from "REPLACE.ME"
+    And request contains "interaction_id" parameter from "REPLACE.ME"
+    When the request is sent
+    Then the response status is 200 OK
+
   @generated @skip @team:DataDog/ml-observability
   Scenario: Get annotated interactions by content IDs returns "Bad Request" response
     Given operation "GetLLMObsAnnotatedInteractionsByTraceIDs" enabled
diff --git a/tests/v2/features/undo.json b/tests/v2/features/undo.json
index 535ebca0b1..f73a9089c8 100644
--- a/tests/v2/features/undo.json
+++ b/tests/v2/features/undo.json
@@ -4636,6 +4636,12 @@
       "type": "safe"
     }
   },
+  "GetLLMObsAnnotatedInteraction": {
+    "tag": "Agent Observability",
+    "undo": {
+      "type": "safe"
+    }
+  },
   "UpsertLLMObsAnnotations": {
     "tag": "Agent Observability",
     "undo": {