diff --git a/.generator/schemas/v2/openapi.yaml b/.generator/schemas/v2/openapi.yaml
index df325279eec0..60d30be4338c 100644
--- a/.generator/schemas/v2/openapi.yaml
+++ b/.generator/schemas/v2/openapi.yaml
@@ -38173,7 +38173,7 @@ components:
             $ref: "#/components/schemas/LLMObsAnnotationItem"
           type: array
         content_id:
-          description: Identifier of the content for this interaction.
+          description: Identifier of the content (trace ID or session ID) for this interaction.
           example: "trace-abc-123"
           type: string
         id:
@@ -38376,7 +38376,7 @@ components:
       description: A single interaction to add to an annotation queue.
       properties:
         content_id:
-          description: Identifier of the content (such as trace ID) for this interaction.
+          description: Identifier of the content (trace ID or session ID) for this interaction.
           example: "trace-abc-123"
           type: string
         type:
@@ -38393,7 +38393,7 @@ components:
           example: false
           type: boolean
         content_id:
-          description: Identifier of the content for this interaction.
+          description: Identifier of the content (trace ID or session ID) for this interaction.
           example: "trace-abc-123"
           type: string
         id:
@@ -39912,11 +39912,13 @@ components:
       enum:
         - trace
         - experiment_trace
+        - session
       example: trace
       type: string
       x-enum-varnames:
         - TRACE
         - EXPERIMENT_TRACE
+        - SESSION
     LLMObsLabelSchema:
       description: Schema definition for a single label in an annotation queue.
       properties:
@@ -104738,7 +104740,7 @@ paths:
         If you have any feedback, contact [Datadog support](https://docs.datadoghq.com/help/).
   /api/v2/llm-obs/v1/annotation-queues/{queue_id}/annotated-interactions:
     get:
-      description: Retrieve all interactions and their annotations for a given annotation queue.
+      description: Retrieve all interactions (traces and sessions) and their annotations for a given annotation queue.
       operationId: GetLLMObsAnnotatedInteractions
       parameters:
         - $ref: "#/components/parameters/LLMObsAnnotationQueueIDPathParameter"
@@ -104787,7 +104789,7 @@ paths:
   /api/v2/llm-obs/v1/annotation-queues/{queue_id}/interactions:
     post:
       description: |-
-        Add one or more interactions (traces) to an annotation queue.
+        Add one or more interactions (traces or sessions) to an annotation queue.
         At least one interaction must be provided.
       operationId: CreateLLMObsAnnotationQueueInteractions
       parameters:
diff --git a/lib/datadog_api_client/v2/api/llm_observability_api.rb b/lib/datadog_api_client/v2/api/llm_observability_api.rb
index cc58db487a77..28c76c4b6501 100644
--- a/lib/datadog_api_client/v2/api/llm_observability_api.rb
+++ b/lib/datadog_api_client/v2/api/llm_observability_api.rb
@@ -109,7 +109,7 @@ def create_llm_obs_annotation_queue_interactions(queue_id, body, opts = {})
 
     # Add annotation queue interactions.
     #
-    # Add one or more interactions (traces) to an annotation queue.
+    # Add one or more interactions (traces or sessions) to an annotation queue.
     # At least one interaction must be provided.
     #
     # @param queue_id [String] The ID of the LLM Observability annotation queue.
@@ -1100,7 +1100,7 @@ def get_llm_obs_annotated_interactions(queue_id, opts = {})
 
     # Get annotated queue interactions.
     #
-    # Retrieve all interactions and their annotations for a given annotation queue.
+    # Retrieve all interactions (traces and sessions) and their annotations for a given annotation queue.
     #
     # @param queue_id [String] The ID of the LLM Observability annotation queue.
     # @param opts [Hash] the optional parameters
diff --git a/lib/datadog_api_client/v2/models/llm_obs_annotated_interaction_item.rb b/lib/datadog_api_client/v2/models/llm_obs_annotated_interaction_item.rb
index ec0d4db000f6..fb01c9d09b07 100644
--- a/lib/datadog_api_client/v2/models/llm_obs_annotated_interaction_item.rb
+++ b/lib/datadog_api_client/v2/models/llm_obs_annotated_interaction_item.rb
@@ -24,7 +24,7 @@ class LLMObsAnnotatedInteractionItem
     # List of annotations for this interaction.
     attr_reader :annotations
 
-    # Identifier of the content for this interaction.
+    # Identifier of the content (trace ID or session ID) for this interaction.
     attr_reader :content_id
 
     # Unique identifier of the interaction.
diff --git a/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_item.rb b/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_item.rb
index 195319884adf..2f8b1b8c7723 100644
--- a/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_item.rb
+++ b/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_item.rb
@@ -21,7 +21,7 @@ module DatadogAPIClient::V2
   class LLMObsAnnotationQueueInteractionItem
     include BaseGenericModel
 
-    # Identifier of the content (such as trace ID) for this interaction.
+    # Identifier of the content (trace ID or session ID) for this interaction.
     attr_reader :content_id
 
     # Type of interaction in an annotation queue.
diff --git a/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_response_item.rb b/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_response_item.rb
index 0602c34900a3..b9887ec352c9 100644
--- a/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_response_item.rb
+++ b/lib/datadog_api_client/v2/models/llm_obs_annotation_queue_interaction_response_item.rb
@@ -24,7 +24,7 @@ class LLMObsAnnotationQueueInteractionResponseItem
     # Whether this interaction already existed in the queue.
     attr_reader :already_existed
 
-    # Identifier of the content for this interaction.
+    # Identifier of the content (trace ID or session ID) for this interaction.
     attr_reader :content_id
 
     # Unique identifier of the interaction.
diff --git a/lib/datadog_api_client/v2/models/llm_obs_interaction_type.rb b/lib/datadog_api_client/v2/models/llm_obs_interaction_type.rb
index 872ef0791e16..f0cdde032576 100644
--- a/lib/datadog_api_client/v2/models/llm_obs_interaction_type.rb
+++ b/lib/datadog_api_client/v2/models/llm_obs_interaction_type.rb
@@ -23,5 +23,6 @@ class LLMObsInteractionType
 
     TRACE = "trace".freeze
     EXPERIMENT_TRACE = "experiment_trace".freeze
+    SESSION = "session".freeze
   end
 end